Novel iron-based compounds, processes for the preparation thereof, and use thereof as catalysts

Abstract

The present invention relates to iron anilido-imine complexes, processes for their preparation and their use as catalysts in the Suzuki-Miyaura reaction.

Description

[0001] Description

[0002] Title: New iron-based compounds, their preparation processes and their use as catalysts

[0003] Technical field

[0004] The present invention relates to the synthesis of novel iron-based compounds, their preparation processes and their use as catalysts.

[0005] State of the art

[0006] Iron is a cheap, abundant, readily available, and low-toxicity metal (Angew. Chem. Int. Ed. 2016, 55, 12150) and is tending to substitute palladium in the chemical industries. Indeed, iron offers many advantages from a sustainable development perspective. Moreover, iron is one of the few base metals that has been successfully tested as a catalyst in industrial cross-coupling processes at the kilogram scale. Iron β-diketiminate complexes have already been used to catalyze hydroamination reactions (Chem. Eur. J. 2019, 25, 835-844). The use of such iron complexes requires working in a controlled atmosphere, in the absence of humidity and ambient air, in glove box-type equipment. (Chem. Eur. J. 2019, 25, 835-844), which represents a constraint that makes these catalysts difficult to use on an industrial scale.

[0007] Indeed, metal catalysis is a way to accelerate, or even make possible, certain reactions and to access a large number of compounds at production costs much lower than conventional organic synthesis routes, which sometimes require a significant number of steps. In addition, the requirements for residual metals in products intended for human use, particularly in products for pharmaceutical use, currently represent a barrier to the use of metal catalysis in the manufacture of such products.

[0008] The development of carbon-carbon bond formation reactions by cross-coupling is one of the greatest revolutions in the field of synthetic organic chemistry. Among the different types of cross-coupling, the Suzuki-Miyaura coupling (Angew. Chem., Int. Ed. 2011, 50, 6722), which is a coupling between a halogenated or pseudohalogenated organic derivative and an organoboron derivative, catalyzed by palladium, is one of the most commonly applied strategies for carbon-carbon bond formation in the pharmaceutical and agrochemical industries and the fine chemicals sector. (Adv. Synth. Catcil. 2009, 351, 3027). For example, in the pharmaceutical industry, the Suzuki-Miyaura coupling is used in nearly 25% of small molecule drug syntheses and accounts for 40% of carbon-carbon bond forming reactions, while other cross-coupling reactions account for less than 5%.Indeed, this coupling is mainly limited to couplings between 2 partners carrying an sp hybridized carbon. 2 (or even sp) leading to the formation of molecules with planar geometry. Indeed, the ease of elimination of the Pd(II)-alkyl intermediates formed during the coupling reaction prevents its generalized extension to coupling partners bearing sp hybridized carbons 3 . Very few molecules with more complex three-dimensional geometry are accessible by palladium catalysis and even fewer when they contain a heteroaromatic unit, which is problematic since nearly 70% of pharmaceutical molecules contain at least one heterocycle (Bioactive Heterocyclic Compound Classes: Pharmaceuticals, Wiley, Weinheim, 2012). In addition, the coupling between 2 partners carrying a sp hybridized carbon 3 represent only 1% of the Suzuki-Miyaura reactions described to date despite the significant presence of C(sp3 )-C(sp 3 ) in natural or biologically active molecules.

[0009] Moreover, the ligands used to stabilize these catalysts commonly used in industry are phosphorus-based ligands. Since nitrogen is more abundant than phosphorus, chemists are turning to the design of nitrogen-based ligands because it is an advantage from the point of view of sustainable development. Although some examples of iron-based catalysts for Suzuki-Miyaura coupling have been described in the state of the art, few have been reported as being effective for the coupling of partners bearing sp hybridized carbons. 3. In addition, they often rely on the use of activated boronic derivatives (using an organolithium or an organomagnesium), which represents significant limitations in terms of functional compatibility and they use catalysts bearing phosphorus-based ligands. In addition, there are few examples of coupling with tertiary halides. The latter are generally halides that are difficult to couple due to their steric hindrance.

[0010] The invention aims to remedy the problem mentioned above and to enable the creation of C(sp 3 )-C(sp 2 ) and C(sp 3 )-C(sp 3 ).

[0011] An object of the present invention relates to novel iron iminoanilide compounds

[0012] Another object of the invention is the use of iron imino-anilide complexes to catalyze the formation of carbon-carbon bonds, in particular, the Suzuki-Miyaura reaction.

[0013] The invention also aims to provide a catalyst stable in ambient air allowing the creation of carbon-carbon bonds.

[0014] Another object of the invention is to provide the processes for preparing iron imino-anilide complexes which can be advantageous in the Suzuki-Miyaura reaction.

[0015] Another object of the invention is to provide novel compounds prepared with the iron iminoanilide complexes

[0016] Description of the invention.

[0017] The present invention relates to the use of at least one of the compounds of general formula (I) below: in which:

[0018] • A is chosen from:

[0019] ▪ a group -X in which X is chosen from a chlorine atom a bromine atom

[0020] ▪ a grouping in which:

[0021] M is a coordinating solvent p is chosen from 1, 2, 3, 4 or a decimal number which can vary from a value greater than 0 but less than 4

[0022] ▪ a grouping

[0023] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0024] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0025] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0026] It was unexpectedly found that iron imino-anilide complexes could catalyze the formation of carbon-carbon bonds.

[0027] A can represent X, this group X being chosen from a chlorine or bromine atom, X(Li-X)- (M) pand (Acac)2In case of steric hindrance due to groups B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 , A advantageously represents X.

[0028] When there is little or no steric hindrance due to the groups B, C, D, E, R1, R2, R3, R4, R5, R1, R7, R8, R9 and R 10 , A advantageously represents XX(Li-X)-(M) p .

[0029] By "coordinating solvent" is meant any solvent capable of stabilizing the electron gap of a metal cation by giving up part of its negative charge using a non-bonding doublet. The coordinating solvent is chosen from the group consisting of diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran. p can take the values ​​of 1, 2, 3, 4 or a decimal number which can vary from a value greater than 0 but less than 4, preferably 1.

[0030] When A represents two acetyloacetonate groups, the compounds do not degrade or lose their properties under the action of ambient air.

[0031] The term "ambient air" refers to the surrounding air naturally present in the atmosphere, the composition of which can vary depending on location or altitude.

[0032] By "linear" is meant the carbon atoms of the alkyl chain, with the exception of those located at the ends of the chain, are all linked one to one through a carbon-carbon bond, in such a way that each carbon atom has only two carbon-carbon bonds, the carbon atom at the beginning of the chain has only one carbon-carbon bond with the rest of the chain and the carbon atom located at the end of the chain has only one carbon-carbon bond.

[0033] The term "branched" means that each carbon atom in the alkyl chain can contain 3 to 4 carbon-carbon bonds.

[0034] The term "catalyst" means a chemical substance which, directly or after transformation by another chemical substance, activates or makes possible a chemical reaction.

[0035] The expression "coupling reaction" designates a carbon-carbon bond formation reaction for carrying out the association of two carbon units and comprising at least one transmetallation step and at least one reductive elimination step. In particular, the coupling reaction also designates a carbon-carbon bond formation reaction for carrying out the association of two carbon units and comprising at least one monoelectronic oxidative addition step or one bielectronic oxidative addition step, at least one transmetallation step and at least one reductive elimination step.

[0036] In a particular embodiment, the invention relates to the use, as defined above, as a catalyst for carrying out a reaction chosen from carbon-carbon bond formation reactions, using an organoboron or an organomagnesium or an organozinc or an organostannous compound, in particular for carrying out the Suzuki-Miyaura reaction.

[0037] The term “organoboron” means an organic compound comprising at least one bond between a carbon atom and a boron atom. For example, without limitation, an organic compound comprising a boronic acid function or a boronic ester function may be mentioned.

[0038] By "organomagnesium" is meant an organic compound comprising at least one bond between a carbon atom and a magnesium atom. For example, but not limited to, the Grignard reagent can be mentioned.

[0039] The term "organozinc" means an organic compound comprising at least one bond between a carbon atom and a zinc atom.

[0040] The term "organostannous" refers to an organic compound comprising at least one bond between a carbon atom and a tin atom.

[0041] In a particular embodiment, the invention relates to the use, as defined above, for carrying out the Suzuki-Miyaura, Kumada and Sonogashira reactions, in particular for carrying out the Suzuki-Miyaura reaction.

[0042] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (I) below:

[0043]

[0044] (I) in which:

[0045] A is chosen from: a group -X in which X is chosen from o a chlorine atom o a bromine atom a group in which:

[0046] ▪ M is a coordinating solvent

[0047] ▪ p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 a grouping

[0048] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms when A corresponds to the group then R1, R5, R6, and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 or 2 or 4 to 10 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms when A corresponds to the -X group or to the group then R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0049] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, the compound of the following formula being excluded:

[0050]

[0051] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below: in which:

[0052] • X is chosen from a chlorine atom and a bromine atom

[0053] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 10 carbon atoms

[0054] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0055] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0056] This structure corresponds to the presence of steric hindrance around the iron atom due to the groups B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10

[0057] To facilitate the understanding of what follows, we arbitrarily consider 3 axes of symmetry (I), (II) (III) as represented in the diagram below

[0058] Axis (I) creates symmetry between C and D, and between B and E. Axis (II) includes the carbon bearing R3 and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between R1 and R5, and between R2 and R4. Axis (III) includes the carbon bearing R8 and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between R6 and R 10 , and between R7 and R9.

[0059] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ib) below: in which:

[0060] • X is chosen from a chlorine atom and a bromine atom

[0061] • M is a coordinating solvent

[0062] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0063] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0064] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0065] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0066] This structure corresponds to the absence of steric hindrance, or to the presence of low steric hindrance around the iron atom due to the groups B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10

[0067] Advantageously, the compound of formula (Ib) has the following formula:

[0068] To facilitate the understanding of what follows, we arbitrarily consider 3 axes of symmetry (I), (II) (III) as represented in the diagram below

[0069]

[0070] Axis (I) creates symmetry between C and D, and between B and E. Axis (II) includes the carbon bearing R3 and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between R1 and R5, and between R2 and R4. Axis (III) includes the carbon bearing R8 and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between R6 and R 10 , and between R7 and R9.

[0071] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of the following general formula (Ic): in which:

[0072] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 , identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0073] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0074] To facilitate the understanding of what follows, we arbitrarily consider 3 axes of symmetry (I), (II) (III) as represented in the diagram below

[0075] Axis (I) creates symmetry between C and D, and between B and E. Axis (II) includes the carbon bearing R3 and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between R1 and R5, and between R2 and R4. Axis (III) includes the carbon bearing R8 and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between R6 and R 10 , and between R7 and R9.

[0076] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below:

[0077] in which:

[0078] • X is chosen from a chlorine atom and a bromine atom

[0079] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others.

[0080] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9

[0081] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0082] This particular embodiment corresponds to an absence of symmetry with respect to the axis (I), the axis

[0083] (II) and axis (III).

[0084] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below:

[0085] in which:

[0086] • X is chosen from a chlorine atom and a bromine atom

[0087] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0088] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0089] ▪ R1 is different from R5 and / or R2 is different from R4 and

[0090] ▪ R6 is identical to R 10 and R7 is identical to R9 or

[0091] ▪ R6 is different from R 10 and / or R7 is different from R9 and

[0092] ▪ R1 is identical to R5 and R2 is identical to R4

[0093] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0094] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I) and the axis (II), and the presence of symmetry with respect to the axis (III).

[0095] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below:

[0096] in which:

[0097] • X is chosen from a chlorine atom and a bromine atom

[0098] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0099] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5R2 is identical to R4R6 is identical to R 10 R7 is identical to R9

[0100] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0101] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I). It also corresponds to the presence of symmetry with respect to the axis (II) and the axis (III)

[0102] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below:

[0103] in which:

[0104] • X is chosen from a chlorine atom and a bromine atom

[0105] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0106] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9

[0107] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0108] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I). It also corresponds to the absence of a symmetry with respect to the axis (II) and the axis (III)

[0109] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below:

[0110] in which:

[0111] • X is chosen from a chlorine atom and a bromine atom

[0112] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0113] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is identical to R9 or R6 is different from R 10 and / or R7 is different from R9 and R1 is identical to R5 and R2 is identical to R4

[0114] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0115] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I) and the axis (III). It also corresponds to the absence of a symmetry with respect to the axis (II).

[0116] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below:

[0117] in which:

[0118] • X is chosen from a chlorine atom and a bromine atom

[0119] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0120] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5R2 is identical to R4R6 is identical to R 10 R7 is identical to R9

[0121] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0122] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I), the axis (II) and the axis (III).

[0123] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below:

[0124] in which:

[0125] • X is chosen from a chlorine atom and a bromine atom

[0126] • B, C, D and E are fluorine atoms

[0127] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 , identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0128] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0129] This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl group carrying the groups B, C, D and E. This has the consequence of modifying the electronic properties of the iron atom of the catalyst.

[0130] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ib) below:

[0131] in which:

[0132] • X is chosen from a chlorine atom and a bromine atom

[0133] • M is a coordinating solvent

[0134] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0135] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others.

[0136] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9

[0137] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0138] This particular embodiment corresponds to an absence of symmetry with respect to the axis (I), the axis (II) and the axis (III). In a particular embodiment, the invention relates to the use, as defined above, the use of at least one of the compounds of general formula (Ib) below: in which:

[0139] • X is chosen from a chlorine atom and a bromine atom

[0140] • M is a coordinating solvent

[0141] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0142] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0143] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0144] ▪ R1 is different from R5 and / or R2 is different from R4 and

[0145] ▪ R6 is identical to R 10 and R7 is identical to R9 or

[0146] ▪ R6 is different from R 10 and / or R7 is different from R9 and

[0147] ▪ R1 is identical to R5 and R2 is identical to R4

[0148] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0149] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I) and the axis (II), and the presence of symmetry with respect to the axis (III).

[0150] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ib) below: in which:

[0151] • X is chosen from a chlorine atom and a bromine atom

[0152] • M is a coordinating solvent

[0153] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0154] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0155] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5R2 is identical to R4R6 is identical to R 10 R7 is identical to R9

[0156] G is selected from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0157] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I). It also corresponds to the presence of symmetry with respect to the axis (II) and the axis (III)

[0158] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ib) below: in which:

[0159] • X is chosen from a chlorine atom and a bromine atom

[0160] • M is a coordinating solvent

[0161] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0162] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0163] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9

[0164] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0165] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I). It also corresponds to the absence of a symmetry with respect to the axis (II) and the axis (III)

[0166] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ib) below: in which:

[0167] • X is chosen from a chlorine atom and a bromine atom

[0168] • M is a coordinating solvent

[0169] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0170] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0171] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is identical to R9 or R6 is different from R 10 and / or R7 is different from R9 and R1 is identical to R5 and R2 is identical to R4

[0172] G is selected from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0173] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I) and the axis (III). It also corresponds to the absence of a symmetry with respect to the axis (II).

[0174] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ib) below: in which:

[0175] • X is chosen from a chlorine atom and a bromine atom

[0176] M is a coordinating solvent p is chosen from 1, 2, 3, 4 or a decimal number which can vary from a value greater than 0 but less than 4

[0177] B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: - R1 is identical to R5 - R2 is identical to R4 - R6 is identical to R 10 R7 is identical to R9

[0178] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0179] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I), the axis

[0180] (II) and axis (III).

[0181] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ib) below: in which:

[0182] • X is chosen from a chlorine atom and a bromine atom

[0183] • M is a coordinating solvent

[0184] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0185] • B, C, D and E are fluorine atoms

[0186] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0187] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0188] This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl group carrying the groups B, C, D and E. This has the consequence of modifying the electronic properties of the iron atom of the catalyst. In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ic) below: in which:

[0189] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0190] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9

[0191] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0192] This particular embodiment corresponds to an absence of symmetry with respect to the axis (I), the axis (II) and the axis (III).

[0193] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of the following general formula (Ie):

[0194] in which:

[0195] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0196] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is identical to R9 or R6 is different from R 10 and / or R7 is different from R9 and R1 is identical to R5 and R2 is identical to R4

[0197] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0198] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I) and the axis (II), and the presence of symmetry with respect to the axis (III).

[0199] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of the following general formula (Ic):

[0200] in which:

[0201] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0202] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5R2 is identical to R4R6 is identical to R 10 R7 is identical to R9

[0203] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0204] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I). It also corresponds to the presence of symmetry with respect to the axis (II) and the axis (III)

[0205] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of the following general formula (Ic):

[0206] in which:

[0207] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0208] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9

[0209] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0210] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I). It also corresponds to the absence of a symmetry with respect to the axis (II) and the axis (III)

[0211] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of the following general formula (Ic):

[0212] in which:

[0213] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0214] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is identical to R9 or R6 is different from R 10 and / or R7 is different from R9 and R1 is identical to R5 and R2 is identical to R4

[0215] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0216] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I) and the axis (III). It also corresponds to the absence of a symmetry with respect to the axis (II).

[0217] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of the following general formula (Ic):

[0218] in which:

[0219] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0220] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5R2 is identical to R4R6 is identical to R 10 R7 is identical to R9

[0221] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0222] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I), the axis (II) and the axis (III).

[0223] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of the following general formula (Ic):

[0224] in which:

[0225] • B, C, D and E are fluorine atoms

[0226] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 , identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0227] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

[0228] This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl group carrying the groups B, C, D and E. This has the consequence of modifying the electronic properties of the iron atom of the catalyst

[0229] In another embodiment, the invention relates, as defined above, to the use of compounds of formula (I), chosen from:

[0230]

[0231] The invention relates in particular to the compound of the following general formula (I):

[0232] A is chosen from: a group -X in which X is chosen from o a chlorine atom o a bromine atom a group in which:

[0233] ▪ M is a coordinating solvent

[0234] ▪ p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 a grouping

[0235] B, C, D, and E, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being other than a hydrogen atom when A corresponds to the group then R1, R5, R6, and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 or 2 or 4 to 10 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9. identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms when A corresponds to the group -X or to the group then R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0236] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms

[0237] In this particular embodiment, at least one of the groups B, C, D and E is other than a hydrogen atom, and there may be presence or absence of symmetry with respect to the (I) axis, the (II) axis or the (III) axis.

[0238] The invention relates in particular to the compound of general formula (I) below:

[0239] A is chosen from: a group -X in which X is chosen from o a chlorine atom o a bromine atom a group in which:

[0240] M is a coordinating solvent ▪ p is chosen from 1, 2, 3, 4 or a decimal number which can vary from a value greater than 0 but less than 4 a group

[0241] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0242] • R1, R5, R6, and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3. a linear or branched alkyl group of 1 to 2 or 4 to 10 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0243] • R2, R3, R4, R6, R7, R8, and R9, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0244] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, the compound of the following formula being excluded:

[0245] In this particular embodiment, there may be presence or absence of symmetry with respect to the axis (I), the axis (II) or the axis (III).

[0246] The invention relates in particular to the compound as defined above, of the following general formula (I):

[0247] in which:

[0248] • A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and G have the meanings indicated above

[0249] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms and at least one of B, C, D or E is other than a hydrogen atom.

[0250] In this particular embodiment, at least one of the groups B, C, D and E is other than a hydrogen atom, and there may be presence or absence of symmetry with respect to the (I) axis, the (II) axis or the (III) axis.

[0251] The invention relates in particular to the compound as defined above, of the following general formula (I): in which:

[0252] • A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and G have the meanings indicated above

[0253] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms and at least one of B, C, D or E is a halogen, in particular F In this particular embodiment, at least one of the groups B, C, D and E is a fluorine atom, and there may be the presence or absence of symmetry with respect to the axis (I), the axis (II) or the axis (III). The invention relates in particular to the compound as defined above, of the following general formula (I): in which

[0254] • A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and G have the meanings indicated above

[0255] • B, C, D, and E are fluorine atoms

[0256] In this particular embodiment, the groups B, C, D and E are fluorine atoms. This has the consequence of modifying the electronic properties of the iron atom of the catalyst, and there is the presence of a symmetry with respect to the (I) axis. There may be the presence or absence of symmetry with respect to the (II) axis or the (III) axis.

[0257] The invention has as its particular subject the compound as defined above, of general formula (Ia) as follows: in which:

[0258] • X is chosen from a chlorine atom and a bromine atom

[0259] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 , identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0260] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms

[0261] The invention has as its particular subject the compound as defined above, of general formula (Ia) as follows: in which X and G have the meanings indicated above, and

[0262] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0263] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9

[0264] In this particular embodiment, there is a presence of symmetry with respect to the axis (I) and an absence of symmetry with respect to the axis (II) and the axis (III).

[0265] The invention has as its particular subject the compound as defined above, of general formula (Ia) as follows:

[0266] in which X and G have the meanings indicated above, and

[0267] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0268] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5R2 is identical to R4R6 is identical to R 10 R7 is identical to R9

[0269] In this particular embodiment, there is a symmetry with respect to the axis (I), the axis (II) and the axis (III)

[0270] The invention relates in particular to the compound as defined above, of the following general formula (Ib):

[0271] in which:

[0272] • X is chosen from a chlorine atom and a bromine atom

[0273] • M is a coordinating solvent

[0274] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0275] • B, C, D and E, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0276] • R1, R5, R6 and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3. a linear or branched alkyl group of 1 to 2 or 4 to 10 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 1 to 20 carbon atoms, and R2, R3, R4, R7, R8, and R9, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0277] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, the compound of the following formula being excluded:

[0278]

[0279] The invention relates in particular to the compound as defined above, of the following general formula (Ib): in which X, M, p and G have the meanings indicated above, and

[0280] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0281] • R1, R5, R6 and R10 , are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 2 or 4 to 10 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and R2, R3, R4, R7, R8, and R9, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a group linear or branched dialkylamino of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9

[0282] In this particular embodiment, there is a presence of symmetry with respect to the axis (I) and an absence of symmetry with respect to the axis (II) and the axis (III)

[0283] The invention relates in particular to the compound as defined above, of the following general formula (Ib): in which X, M, p and G have the meanings indicated above, and

[0284] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0285] • R1, R5, R6 and R 10, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 2 or 4 to 10 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and R2, R3, R4, R6, R7, and R9, which are identical, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5R2 is identical to R4R6 is identical to R 10 R7 is identical to R9, the compound of the following formula being excluded:

[0286] In this particular embodiment, there is a symmetry with respect to the axis (I), the axis (II) and the axis (III).

[0287] The invention relates in particular to the compound of the following general formula (Ie): in which:

[0288] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0289] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0290] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms

[0291] The invention has as its particular subject the compound as defined above, of the following general formula (Ic): in which:

[0292] • B, C, D and E are chosen from: a hydrogen atom, a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0293] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5R2 is identical to R4R6 is identical to R 10 R7 is identical to R9

[0294] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms

[0295] In this particular embodiment, there is a symmetry with respect to the axis (I), the axis (II) and the axis (III).

[0296] The invention has as its particular subject the compound as defined above, of the following general formula (Ic):

[0297] in which:

[0298] • B, C, D and E are chosen from: a hydrogen atom, a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0299] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is identical to R9 or R6 is different from R 10 and / or R7 is different from R9 and R1 is identical to R5 and R2 is identical to R4

[0300] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms

[0301] In this particular embodiment, there is a symmetry with respect to the axis (I). There is also the absence of a symmetry with respect to the axis (II) and the axis (III)

[0302] The invention has as its particular subject the compound as defined above chosen from:

[0303]

[0304] In a particular embodiment, the present invention relates to the use of at least one of the compounds of formulae (Ia), (Ib) or (Ic) as defined above as a catalyst for carrying out a reaction, chosen from carbon-carbon bond formation reactions such as the Suzuki-Miyaura, Kumada and Sonogashira reactions,

[0305] The term "carbon-carbon bond formation reaction" means that in the reaction balance, a carbon-carbon bond will have been created between two distinct molecules or intramolecularly.

[0306] In another embodiment, the compound of formula (Ia), (Ib) or (Ic) is used, as defined above, at catalytic loadings of 0.01 mol% to 0.1 mol%, 0.1 mol% to 1 mol%, 1 mol% to 10 mol%, 10 mol% to 20 mol% and 20 mol% to 30 mol%, preferably 1 mol% to 10 mol%.

[0307] The term "catalytic charge" refers to the molar equivalent percentage at which the catalyst is introduced.

[0308] In another embodiment, the invention relates to the use of the compounds, as defined above, in order to carry out the Suzuki-Miyaura reaction.

[0309] As a non-limiting example, the Suzuki-Miyaura reaction is carried out in the presence of a halogenated derivative, a boronic ester and a base (1 / 2 / 1, 2 or 2) and the catalyst with stirring at 25°C for 24 hours.

[0310] The use of these compounds in a Suzuki-Miyaura reaction can be done in benzene, toluene, 2-methyltetrahydrofuran, methyl tert-butyl ether, tert-amyl methyl ether or anisole, preferably in benzene.

[0311] These catalysts can be activated in a Suzuki-Miyaura reaction by thermal heating, by microwave, preferably by thermal heating.

[0312] The reaction medium can be heated to temperatures from 25°C to 150°C, preferably at 25°C. The use of these catalysts in a Suzuki-Miyaura reaction can be done in batch or continuous flow, preferably in batch.

[0313] In another embodiment, the invention relates to the use of the compounds, as defined above, in which the implementation of the Suzuki-Miyaura reaction comprises the use of a base chosen from LiNMeEt, LiNMe2, LiNEt2, LiNiPr2, LiNTMS2, LiNPhMe, in particular LiNMeEt and LiNMe2. In another embodiment, the invention relates to the use as defined above, for the synthesis of one of the compounds of the following formula:

[0314]

[0315] in which Y is chosen from:

[0316] ▪ a hydrogen atom

[0317] ▪ a linear or branched alkyl group of 1 to 10 carbon atoms

[0318] ▪ a linear or branched alkoxyl group of 1 to 10 carbon atoms

[0319] ▪ a -OPh group

[0320] ▪ an alkylamino or dialkylamino group, substituted by one or two linear alkyl groups of 1 to 10 carbon atoms

[0321] ▪ a halogen, in particular a fluorine atom, a chlorine atom or a bromine atom a nitro group NO2 a trifluoromethyl group CF3

[0322] ▪ a group

[0323] The invention relates in particular to the new compound of the following formula:

[0324] The invention relates in particular to the new compound of the following formula:

[0325] The invention relates in particular to the new compound of the following formula:

[0326] The invention relates in particular to the new compound of the following formula:

[0327] The invention relates in particular to the new compound of the following formula:

[0328] The invention relates in particular to the new compound of the following formula:

[0329] In another embodiment, the invention relates to the use as defined above of a compound of formula (Ia), (Ib) or (Ic) for carrying out a Suzuki-Miyaura reaction from a compound of formula (SI) in which W is chosen from: a phenyl group in which Y is chosen from:

[0330] ▪ a hydrogen atom

[0331] ▪ a linear or branched alkyl group of 1 to 10 carbon atoms

[0332] ▪ a linear or branched alkoxyl group of 1 to 10 carbon atoms

[0333] ▪ a -OPh group

[0334] ▪ an alkylamino or dialkylamino group, substituted by one or two linear alkyl groups of 1 to 10 carbon atoms

[0335] ▪ a halogen, in particular a fluorine atom, a chlorine atom or a bromine atom

[0336] . a nitro group NO2

[0337] . a trifluoromethyl group CF3

[0338] ▪ a grouping a 2-thiophenyl group a 3-fiiranyl group a 2-naphthyl group a 6-quinolyl group a group a group a group a group a group a group a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, in particular an octyl group a group and V is chosen from: a group in which q is equal to 0 or 1. a grouping with a compound of formula (S2): Z-Hal in which Z is chosen from: a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, in particular an octyl, hexyl, cycloheptyl, cyclopentyl or cyclopropyl group a 1-adamantyl group of formula a benzyl group of formula a group a group a group a group a group a group a group a group and Hal is chosen from: a chlorine atom a bromine atom an iodine atom

[0339] In one embodiment, the present invention relates to a process for preparing a compound of formula (Ia) as defined above: in which:

[0340] • X is chosen from a chlorine atom and a bromine atom

[0341] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0342] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 , identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0343] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms comprising a step of sequential addition of n-butyllithium then iron (II) halide FeX2 to a compound of formula (II)

[0344] in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above.

[0345] In this embodiment, the addition reaction here consists of the deprotonation of the secondary amine function of compound (II) located between two phenyl groups in order to create the N-Fe bond. Lithium does not coordinate to compound (Ia) due to the steric hindrance around the iron atom due to the groups B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10The compound (la) obtained is sensitive to oxygen and must be stored under inert atmospheric conditions. In another embodiment, the present invention relates to a preparation process, as defined above, in which the above-mentioned addition step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran, from -78°C to 25°C, preferably at -78°C, for 30 minutes, then 2 hours at 25°C, then 15 hours with stirring.

[0346] The term "ethereal solvent" refers to a solvent in which there is at least one ether function.

[0347] This sequential addition can be carried out either in a single solvent, or in a first solvent for the addition of n-butyllithium, then after evaporation of this solvent, in a second solvent for the addition of FeX2.

[0348] As a non-limiting example, this step of sequential addition of n-butyllithium and FeX2(1 / 1) can be carried out for the addition of n-butyllithium in hexane, then for the addition of FeX2 in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole.

[0349] As a non-limiting example, this step of sequential addition of n-butyllithium and FeX2(1 / 1) can be carried out for the addition of n-butyllithium in a non-coordinating apolar solvent in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, then for the addition of FeX2 in tetrahydrofurane.

[0350] By "non-coordinating apolar solvent" we mean a solvent whose barycenter of the sums of the electronegativity differences are the same,

[0351] As a non-limiting example, this step of adding n-butyllithium and Fe2 chloride (1 / 1) can be carried out in tetrahydrofiirane at temperatures of -78°C to 25°C, preferably -78°C to -30°C for 30 minutes, then 2 hours from -78°C to 25°C, preferably from 0°C to 25°C, then 15 hours from -78°C to 25°C, preferably from 0°C to 25°C with stirring.

[0352] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (II):

[0353] in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above, said step comprising a step of aromatic nucleophilic substitution of a compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom on a compound of formula (IV): in which R6, R7, R8, R9, and R 10 have the meanings indicated above to obtain said compound of formula (II) the compounds of the following formula being excluded:

[0354]

[0355] In this embodiment, the aromatic nucleophilic substitution occurs via the lithium amide of compound (IV) substituting for the fluorine of compound (III).

[0356] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above-mentioned aromatic nucleophilic substitution step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran and at a temperature of 25°C to 125°C, preferably at 25°C.

[0357] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0358] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above-mentioned aromatic nucleophilic substitution step is carried out in a non-coordinating apolar solvent, in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, preferably in toluene and at a temperature of 25°C to 125°C, preferably at 25°C or 90°C.

[0359] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0360] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (III)

[0361] in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom, said step comprising a condensation reaction of a compound of formula (V) in which B, C, D, and E have the meanings indicated above, and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain said compound of formula (III) the compounds of the following formula being excluded:

[0362]

[0363] In this embodiment, the condensation step forming compound (III) is carried out from an aldehyde, compound (V) and an amine, compound (IV).

[0364] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above condensation step is carried out, at a temperature of 0°C to 150°C, in a non-coordinating apolar or alcoholic solvent, in particular chosen from hexane, toluene, benzene, cyclohexane, methylcyclohexane, butan-1-ol, butan-2-ol, isobutanol, tert-butanol, propan-2-ol, isopropanol, methanol, or ethanol, preferably hexane at 25°C, or preferably toluene at 150°C, or preferably ethanol at 90°C.

[0365] The term "alcoholic solvent" refers to a solvent that contains a hydroxyl function.

[0366] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1) is carried out in the presence of MgSO4 (0.08 mol%) in hexane at temperatures of 25°C to 75°C, preferably at 25°C.

[0367] As a non-limiting example, this condensation of an aldehyde and an amine is carried out in the presence of para-toluenesulfonic acid (1 / 1.1 / 0.01) in toluene at temperatures of 25°C to 150°C, preferably at 150°C.

[0368] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1,1) is carried out in ethanol at temperatures of 25°C to 90°C, preferably at 25°C.

[0369] In another embodiment, the present invention relates to a process for the preparation, as defined above, of a compound of formula (Ia)

[0370] in which:

[0371] • X is chosen from a chlorine atom and a bromine atom

[0372] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0373] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 , identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0374] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atoms comprising: a) a step of condensation of a compound of formula (V) in which in which B, C, D, and E have the meanings indicated above and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom b) a step of aromatic nucleophilic substitution of said compound of formula (III) on a compound of formula (IV): in which R6, R7, R8, R9, and R 10 have the meanings indicated above to obtain the compound of formula (II)

[0375] in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the meanings indicated above c) a step of sequential addition of n-butyl lithium then iron (II) halide FeX2 on said compound of formula (II) to obtain the compound of formula (Ia).

[0376] In another embodiment, the present invention relates to a process for the preparation, as defined above, of a compound of formula (Ib): in which:

[0377] • X is chosen from a chlorine atom and a bromine atom

[0378] • M is a coordinating solvent

[0379] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0380] B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0381] • R1, R2, R3, R4, R5, R, R7, R8, R9and R 10 , identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0382] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms comprising a step of sequential addition of n-butyllithium then iron (II) halide FeX2 to a compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above.

[0383] In this embodiment, the addition reaction here consists of the deprotonation of the secondary amine function of compound (II) located between two phenyl groups in order to create the N-Fe bond. A first X atom linked to iron coordinates to a lithium atom, itself already coordinated by another X atom. This coordination can occur in the absence or presence of a low steric hindrance around the iron atom due to the groups B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10The resulting compound is sensitive to ambient air and must be stored under inert atmospheric conditions.

[0384] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above-mentioned addition step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran, from -78°C to 25°C, preferably at -78°C, for 30 minutes, then 2 hours at 25°C, then 15 hours at 25°C with stirring. This sequential addition can be carried out either in a single solvent, or in a first solvent for the addition of n-butyllithium, then after evaporation of this solvent, in a second solvent for the addition of FeCX2.

[0385] As a non-limiting example, this step of sequential addition of n-butyllithium and FeX2(1 / 1) can be carried out for the addition of n-butyllithium in hexane, then for the addition of FeX2 in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole.

[0386] As a non-limiting example, this step of sequential addition of n-butyllithium and FeX2(1 / 1) can be carried out for the addition of n-butyllithium in a non-coordinating apolar solvent in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, then for the addition of FeX2 in tetrahydrofuran.

[0387] As a non-limiting example, this step of adding n-butyllithium and FcCF (1 / 1) can be carried out in tetrahydrofuran at temperatures from -78°C to 25°C, preferably from -78°C to -30°C for 30 minutes, then 2 hours from -78°C to 25°C, preferably from 0°C to 25°C, then 15 hours from -78°C to 25°C, preferably from 0°C to 25°C with stirring.

[0388] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (II): in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above, said step comprising a step of aromatic nucleophilic substitution of a compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom on a compound of formula (IV): in which R6, R7, R8, R9, and R 10 have the meanings indicated above to obtain said compound of formula (II) the compounds of the following formula being excluded:

[0389] In this embodiment, the aromatic nucleophilic substitution occurs via the lithium amide of compound (IV) substituting for the fluorine of compound (III).

[0390] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above-mentioned aromatic nucleophilic substitution step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran and at a temperature of 25°C to 125°C, preferably at 25°C.

[0391] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0392] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above-mentioned aromatic nucleophilic substitution step is carried out in a non-coordinating apolar solvent, in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, preferably in toluene and at a temperature of 25°C to 125°C, preferably at 25°C or 90°C.

[0393] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0394] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom, said step comprising a condensation reaction of a compound of formula (V) in which B, C, D, and E have the meanings indicated above, and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain said compound of formula (III) the compounds of the following formula being excluded:

[0395] ]

[0396] In this embodiment, the condensation step forming the imine of compound (III) is carried out from an aldehyde, compound (V) and an amine, compound (IV).

[0397] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above condensation step is carried out, at a temperature of 0°C to 150°C, in a non-coordinating apolar or alcoholic solvent, in particular chosen from hexane, toluene, benzene, cyclohexane, methylcyclohexane, butan-1-ol, butan-2-ol, isobutanol, tert-butanol, propan-2-ol, isopropanol, methanol, or ethanol, preferably hexane at 25°C, or preferably toluene at 150°C or preferably ethanol at 90°C.

[0398] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1) is carried out in the presence of MgSO4 (0.08 mol%) in hexane at temperatures of 25°C to 75°C, preferably at 25°C.

[0399] As a non-limiting example, this condensation of an aldehyde and an amine is carried out in the presence of para-toluenesulfonic acid (1 / 1.1 / 0.01) in toluene at temperatures of 25°C to 150°C, preferably at 150°C.

[0400] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1,1) is carried out in ethanol at temperatures of 25°C to 90°C, preferably at 25°C.

[0401] In another embodiment, the present invention relates to a process for the preparation, as defined above, of a compound of formula (Ib)

[0402] in which:

[0403] • X is chosen from a chlorine atom and a bromine atom

[0404] • M is a coordinating solvent

[0405] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0406] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 10 carbon atoms

[0407] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 , identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0408] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) comprising: a) a step of condensation of a compound of formula (V) in which in which B, C, D, and E have the meanings indicated above and F is a fluorine atom in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom b) a step of aromatic nucleophilic substitution of said compound of formula (III) on a compound of formula (IV): in which R6, R7, R8, R9, and R 10 have the meanings indicated above to obtain the compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10have the meanings indicated above c) a step of sequential addition of n-butyl lithium then iron (II) halide FeX2 on said compound of formula (II) to obtain the compound of formula (Ib).

[0409] In a particular embodiment, the present invention relates to a process for the preparation, as defined above, of a compound of formula (Ic): in which:

[0410] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0411] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0412] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms comprising a step of sequential addition of n-butyl lithium, then iron (III) tris-acetylacetonate to a compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above to obtain said compound of formula (Ic).

[0413] In this embodiment, the addition reaction here consists of the deprotonation of the secondary amine function of compound (II) located between two phenyl groups in order to create the N-Fe bond. The compounds of formula (Ie) thus obtained are stable in ambient air.

[0414] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above-mentioned addition step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran, from -78°C to 25°C, preferably at 25°C, then 16h at 25°C with stirring.

[0415] This sequential addition can be carried out either in a single solvent, or in a first solvent for the addition of n-butyllithium, then after evaporation of this solvent, in a second solvent for the addition of Fe(acac)3.

[0416] As a non-limiting example, this step of sequential addition of n-butyllithium and Fe(acac)3(1 / 1) can be carried out for the addition of n-butyllithium in hexane, then for the addition of Fe(acac)3 in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole.

[0417] As a non-limiting example, this step of sequential addition of n-butyllithium and Fe(acac)3(1 / 1) can be carried out for the addition of n-butyllithium in a non-coordinating apolar solvent in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, then for the addition of Fe(acac)3 in tetrahydrofuran.

[0418] As a non-limiting example, this step of adding n-butyllithium and Fe(acac)3(1 / 1) can be carried out in tetrahydrofiirane at temperatures of -78°C to 25°C, preferably -78°C to -30°C for 30 minutes, then 2 hours from -78°C to 25°C, preferably from 0°C to 25°C, then 16 hours from -78°C to 25°C, preferably at 25°C.

[0419] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (II): in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above, said step comprising a step of aromatic nucleophilic substitution of a compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom on a compound of formula (IV): in which R6, R7, R8, R9, and R 10 have the meanings indicated above to obtain said compound of formula (II). In this embodiment, the aromatic nucleophilic substitution occurs via the lithium amide of compound (IV) replacing the fluorine of compound (III).

[0420] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above-mentioned aromatic substitution step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran and at a temperature of 25°C to 125°C, preferably at 25°C.

[0421] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0422] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above-mentioned addition step is carried out in a non-coordinating apolar solvent, in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, preferably in toluene and at a temperature of 25°C to 125°C, preferably at 25°C or 90°C.

[0423] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures of 25°C to 125°C, preferably 90°C to 125°C. As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures of 25°C to 125°C, preferably 25°C to 75°C.

[0424] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom said step, comprising a step of condensation of a compound of formula (V) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above, to obtain said compound of formula (III).

[0425] In this embodiment, the step of forming the imine of compound (III) is carried out from an aldehyde, compound (V) and an amine, compound (IV).

[0426] In another embodiment, the present invention relates to a preparation process, as defined above, in which the above condensation step is carried out, at a temperature of 0°C to 150°C, in a non-coordinating apolar or alcoholic solvent, in particular chosen from hexane, toluene, benzene, cyclohexane, methylcyclohexane, butan-1-ol, butan-2-ol, isobutanol, tert-butanol, propan-2-ol, isopropanol, methanol or ethanol, preferably hexane at 25°C, or preferably in toluene at 150°C or preferably in ethanol at 90°C.

[0427] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1) is carried out in the presence of MgSO4 (0.08 mol%) in hexane at temperatures of 25°C to 75°C, preferably at 25°C.

[0428] As a non-limiting example, this condensation of an aldehyde and an amine is carried out in the presence of para-toluenesulfonic acid (1 / 1.1 / 0.01) in toluene at temperatures of 25°C to 150°C, preferably at 150°C.

[0429] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1,1) is carried out in ethanol at temperatures of 25°C to 90°C, preferably at 25°C.

[0430] In another embodiment, the present invention relates to a process for the preparation, as defined above, of a compound of formula (Ic) in which: • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0431] • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0432] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atoms comprising: a) a step of condensation of a compound of formula (V) in which B, C, D, and E have the meanings indicated above, and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom b) a step of aromatic nucleophilic substitution of said compound of formula (III) on a compound of formula (IV): in which R6, R7, R8, R9, and R 10 have the meanings indicated above to obtain the compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above, c) a step of sequential addition of n-butyl lithium then iron (III) tris-acetylacetonate to said compound of formula (II) to obtain said compound of formula (Ic).

[0433] Examples

[0434] Materials and methods

[0435] NMR spectra 1 H and 13 C were made at 298 K on a Bruker AM250, AV300 or AV360 MHz Bruker spectrometer. The NMR spectra of the 7 Li and du 19F were made at 295 K on a Bruker 300 and 250 spectrometer respectively. The chemical shifts of the spectra of the 1 H were measured using an internal reference which is residual protonated CHCI3 in CDCI3 (7.24 ppm) or residual protonated benzene in benzene-de (7.16 ppm).

[0436] Elemental analyses were performed at Analytische Laboratorien GMBH in Lindlar, Germany.

[0437] High-resolution mass spectra were measured by electrospray ionization (ESI) with a Bruker MicrOTOFq time-of-flight mass spectrometer or a Waters LCT spectrometer using electrospray ionization-time-of-flight (ESI-TOF) mass spectrometry. The following are general procedures for the preparation of compounds of formula (Ia), (II) and (III). in which the groups R2, R4, R7 and R< represent a hydrogen atom, and the groups R1, R3, R5, R6, R8 and R 10have the meanings indicated in the following table [Table 1]

[0438] Procedure A1: The appropriate aniline derivative (1 eq) is added with stirring to a solution of the appropriate 2-fluorobenzaldehyde derivative (1 eq) and MgSO4 in Thexane (c = 1.6 M) at 25 °C. The solution is stirred for 2 h at this temperature then filtered, concentrated under reduced pressure and cooled to -20 °C to give the corresponding compound (III) in the form of yellow crystals.

[0439] Procedure A2: In a Dean-Stark apparatus, para-toluenesulfonic acid (0.01 eq) is added with stirring to a solution of the appropriate 2-fluorobenzaldehyde derivative (1 eq) and the appropriate aniline derivative (1.1 eq) in toluene (c = 0.40 M). The solution is heated at 150°C for 15 h. Then, the solution is cooled to 25°C before the addition of saturated aqueous Na2CO3 solution. The aqueous phase is separated and extracted with Et2O. The organic phases are combined, dried over MgSO4, filtered and concentrated under reduced pressure to give a slightly yellow oil. Recrystallization from Thexane at -20°C gives the corresponding compound (III) as yellow crystals.

[0440] Procedure A3: 2,6-Diisopropylamine (1.1 eq) is added to a solution of perfluorobenzaldehyde (1 eq) in EtOH (c = 1.5 M) at 25 °C and the solution is stirred at this temperature for 2 h. The solution is concentrated under reduced pressure and then cooled to -20 °C, the corresponding compound (III) is obtained in the form of yellow crystals.

[0441] Procedure Bl: A solution of n-butyllithium (n-Buli) (1 eq) is added with stirring to a solution of the appropriate aniline derivative (1 eq) in tetrahydrofuran (THF) (c = 1 M) at -78 °C. The solution is stirred for 15 h and then is cannulated into a solution of the appropriate compound (III) (1 eq) in THF (c = 1 M) at 25 °C. The solution is stirred for 2 h at this temperature and then water is added. The aqueous phase is separated and extracted with hexane. The organic phases are combined, dried over MgSO4, filtered and concentrated under reduced pressure to give a brown oil. Recrystallization from hot ethanol or at -20 °C gives the corresponding compound (II) as yellow crystals.

[0442] Procedure B2: The appropriate compound (III) (1 eq) is added to a suspension of lithium (2,6-diisopropylphenyl)amide (2.5 eq) in toluene (10 mL) at 25 °C. The solution is heated at 90 °C with stirring for 72 h or at 25 °C for 48 h. Then, the solution is cooled to 25 °C before the addition of a saturated aqueous solution of Na2CO3. The aqueous phase is separated and extracted with Et2O. The organic phases are combined, dried over MgSO4, filtered and concentrated under reduced pressure to give a slightly brown oil. Recrystallization from hot EtOH gives the corresponding compound (II) as pale yellow crystals.

[0443] Procedure B3: TiCl (0.5 eq) was added to a solution of 2,6-diisopropylaniline (3 eq) in hexane (c = 1 M) while stirring at 0 °C. The solution was stirred at 25 °C for 24 h. Then the solution was heated to reflux and a solution of 2-fluoroacetophenone (1 eq) in hexane (c = 2.6 M) was added. The solution was heated to reflux for 16 h. A brown solid appeared in the solution. The solution was filtered and the solid was washed with hexane. The organic phases were combined and washed with water. The aqueous phase was separated and then extracted with hexane. The organic phases were combined and dried with MgSO4, filtered and concentrated in vacuo until a yellow oil appeared. n-BuLi (1 eq) was added to a stirred solution of 2,6-diisopropylaniline (1 eq) in THF (c = 1 M) at -78 °C.The solution is stirred for 18 hours, then is deposited using a cannula into the solution of the yellow oil previously synthesized in THF at 25°C. The solution is stirred for 2 hours at 25°C. Then water is added to the medium. The aqueous phase is separated, then extracted with Et2O. The organic phases are combined, dried with MgSO4, filtered and the solvent is evaporated under vacuum to obtain a slightly brown oil. The slightly brown oil is recrystallized from hot ethanol to obtain the corresponding compound (II) in the form of a pale white powder.

[0444] Procedure Cl: n-BuLi (1.6 eq) is added with stirring to a solution of the appropriate compound (III) (1 eq) in THF (c = 0.4 M) at -78 °C. The cooling bath is removed 30 min after the addition. The solution is stirred for 2 h at 25 °C. Then, FeCl2 (1 eq) is added. The solution is stirred for 15 h at 25 °C and then the solvent is evaporated under reduced pressure. The residual solid is washed with hexane and then extracted with Et2O. The dark red solution is concentrated and cooled to -20 °C to give a dark red powder of the corresponding compound (Ia).

[0445] EXAMPLE 1: Synthesis of (E)-N-mesityl-l-(perfluorophenyl)methanimine 2,4,6-Trimethylaniline (2.3 mL, 16.05 mmol) was added to a solution of perfluorobenzaldehyde (1.8 mL, 15 mmol) in EtOH (10 mL) at 25 °C and the solution was refluxed (90 °C) for 16 h. After evaporation of the solvent and recrystallization from Et2O at -20 °C, (E)-A-mesityl- l - (perfluorophenyl)methanimine (4.4 g, 14 mmol, 94%) was obtained as yellow crystals. 1 H NMR (360 MHz, CDCl3, 25°C) δ ppm 8.36 (s, 1H, NH), 6.91 (s, 2H, H Ar), 2.30 (s, 3H, p-Me), 2.15 (s, 6H, o-Me). ). 13 C NMR (90 MHz, CDCl3, 25°C) 5 151.6, 148.4, 134.2, 129.0, 126.5, 20.8, 18.1. MS- HR (ESI) m / z calculated for C16H13F5N [M+H] + 314.0963, found: 314.0957.

[0446] EXAMPLE 2: Synthesis of (E)-N-(2-ethylphenyl)-l-(pentafluorophenyl)methanimine

[0447] 2-Ethylaniline (2.0 mL, 16.5 mmol) was added to a solution of perfluorobenzaldehyde (1.8 mL, 15 mmol) in EtOH (10 mL) at 25 °C and the solution was refluxed (90 °C) for 16 h. After evaporation of the solvent and recrystallization from ether at -20 °C, (E)-N-(2 -ethylphenyl)- 1- (pentafluorophenyl)methanimine (3.7 g, 13.3 mmol, 82%) was obtained as yellow crystals. 1 H NMR (360 MHz, CDCl3, 25 °C) δ ppm 8.59 (s, 1H, NH), 7.34-7.26 (m, 3H, H Ar), 7.03-6.98 (m, 1H, H Ar), 2.84 (q, 2H, J = 7.5 Hz, CH2CH3), 1.26 (t, 3H, J = 7.5 Hz, CH2CH3). 13 C NMR (90 MHz, CDCl3, 25°C) 5 149.8, 147.3, 138.8, 129.0, 127.4, 126.9, 116.9, 24.8, 14.9. MS-HR (ESI) m / z calculated for C15H11F5N [M+H] + 300.0806, found: 300.0799.

[0448] EXAMPLE 3: Synthesis of (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesitylimino)methyl)aniline

[0449] (E)-N-mesityl-l-(perfluorophenyl)methanimine (2.5 g, 8 mmol) is added to a solution of lithium 2,4,6-trimethylphenylamide (2.8 g, 20 mmol) in toluene (16 mL) and then stirred for 48 h at 25°C. After the addition of a saturated solution of NaHCO3 (50 mL), the aqueous phase is extracted with EtOAc (50 mL). The organic phases are combined, dried over MgSO4, filtered and concentrated under reduced pressure. Recrystallization from MeOH at -20°C is carried out and gives pale yellow crystals of the product (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesitylimino)methyl)aniline (3.3 g, 7.7 mmol, 96%) 1 H NMR (360 MHz, CDCl3, 25 °C) δ ppm 10.94 (s, 1H, NH), 8.66 (s, 1H, ArCHN), 6.92-6.90 (m, 4H, H Ar), 2.30 (s, 6H, p-Me), 2.22 (s, 6H, o-Me), 2.15 (s, 6H, o-Me). 13 C { 19F} NMR (100 MHz, CDCl3, 25°C) δ ppm 157.8, 147.5, 137.6, 135.9, 135.8, 135.4, 135.3, 135.1, 134.1, 131.9, 129.5, 129.0, 128.5, 127.3, 102.5, 20.9, 20.7, 18.4. MS-HR (ESI) m / z calculated for C25H25F4N [M+H] + 429.1948, found: 429.1934.

[0450] EXAMPLE 4: Synthesis of (E)-N-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3,4,5,6-tetrafluoroaniline

[0451] (E)-N-(2-ethylphenyl)-l-(pentafluorophenyl)methanimine (2.4 g, 8 mmol) was added to a solution of lithium 2-(ethylphenyl)amide (2.5 mL, 20 mmol) in toluene (16 mL) and stirred for 48 h at 25°C. After the addition of saturated NaHCOs solution (50 mL), the aqueous phase was extracted with EtOAc (50 mL). The organic phases were combined, dried over MgSO4, filtered and concentrated under reduced pressure. Recrystallization from MeOH at -20°C gave pale yellow crystals of the product (E)-A-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3, 4,5,6-tetrafluoroaniline (2.7 g, 6.75 mmol, 84%). 1 H NMR (360 MHz, CDCl3, 25 °C) δ ppm 10.91 (s, 1H, NH), 8.84 (s, 1H, ArCHN), 7.32-7.23 (m, 4H, H Ar), 7.21-7.12 (m, 2H, H Ar), 7.04-7.00 (m, 2H, H Ar), 2.81-2.70 (m, 4H, CH2CH3), 1.26 (t, 3H, J = 7.5 Hz, CH2CH3), 1.13 (t, 3H, J = 7.5 Hz, CH2CH3). 13 C { 19F} NMR (100 MHz, CDCl3, 25°C) δ ppm 153.9, 149.1, 139.3, 137.7, 137.0, 133.7, 132.9, 131.3, 128.9, 128.6, 127.1, 127.0, 126.1, 124.8, 122.2, 118.2, 106.0, 24.9, 24.7, 14.8, 14.2. MS-HR (ESI) m / z calculated for C23H21F4N2 [M+H] + 401.1635, found: 401.1621.

[0452] EXAMPLE 5: Synthesis of P5

[0453] n-BuLi (2.5 M in hexane) (2 mL, 5 mmol) was added with stirring to a solution of (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesitylimino)methyl)anilinc (2.1 g, 5 mmol) in THF (10 mL) at -78 °C. The cooling bath was removed 30 minutes after the addition. The solution was stirred for 4 h at 25 °C. Then, FeCl2 (0.63 g, 5 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane or pentane (10 mL) and extracted with Et2O (25 mL). The ethereal solution was filtered, concentrated, and replaced with hexane (20 mL). After adding a few drops of THF and cooling to -20°C, red crystals of product P5 (2.09 g, 3.0 mmol 60%) are obtained. Elemental analysis calculated for C 25 H 23 Cl2F4FeLiN2(C4H8O)2: C, 56.19; H, 5.57; N, 3.97, found: C, 54.53; H 5.92; N 4.15. 1H RMN (360 MHz, C6D6-50 μL THF-d8, 25 °C) δ ppm 71.05 (s, 3H, p-Me), 33.95 (s, 3H, p-Me), 25.51 (s, 2H, m-H Ar), 24.01 (br s, 6H, o-Me), 14.16 (s, 2H, m-H Ar), 4.37 (br s, 12H, THF), 2.15 (br s, 6H, o-Me), 1.69 (br s, 12H, THF). 7Li NMR (117 MHz, C6D6-50 μL THF-d8, 25 °C) δ ppm 239.6 (br s).

[0454] EXEMPLE 6 : Synthèse de P6

[0455] n-BuLi (2.5 M in hexane) (2 mL, 5 mmol) was added with stirring to a solution of (E)-N-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3,4,5,6-tetrafluoroaniline (2 g, 5 mmol) in THF (10 mL) at -78 °C. The cooling bath was removed 30 minutes after the addition. The solution was stirred for 4 h at 25 °C. Then, FeCl2 (0.63 g, 5 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane or pentane (10 mL) and extracted with Et2O (25 mL). The ethereal solution was filtered, concentrated, and replaced with hexane (20 mL). After adding a few drops of THF and cooling to -20°C, red crystals of product P6 (1.1 g, 1.6 mmol, 35%) are obtained. Elemental analysis calculated for C 23 H 19Cl2F4FeLiN2(C4H8O)2: C, 54.97 H, 5.21; N, 4.14, trouvé: C, 51.13; H 4.90; N 4.40. 1H RMN (250 MHz, C6D6-50 μL THF-d8, 25 °C) δ ppm 34.58 (br s, 1H, H Ar), 26.05 (s, 1H, H Ar), 23.66 (s, 1H, H Ar), 14.94 (s, 2H, H Ar), 12.90 (s, 1H, H Ar), 4.94 (br s, 10H, THF), 1.91 (br s, 10H, THF), -7.84 (br s, 4H, CH2), -10.46 (br s, 6H, CH3), -37.60 (s, 1H, H Ar), -71.64 (s, 1H, H Ar), -87.68 (br s, 1H, ArCHN).

[0456] EXEMPLE 7 : Synthèse de P7

[0457] n-BuLi (2.5 M in hexane) (2.8 mL, 7 mmol) was added with stirring to a solution of (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesitylimino)methyl)aniline (3 g, 7 mmol) in THF (15 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 4 h at 25 °C and concentrated under reduced pressure to give (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesitylimino)methyl)aniline lithium amide. To a solution of Fe(acac)3 (2.1g, 6 mmol) in THF (12 ml) is added with stirring the lithium amide of (E)-2.3.4.5- tetrafluoro-N-mesityl-6-((mesitylimino)methyl)aniline (2.6g, 6 mmol) in THF (6 ml) at 25 °C, then the solution is stirred for 16 h at the same temperature. The red solution becomes dark green. After cooling to - 20 °C, a fusion on celite is carried out as well as an evaporation, the solid is washed with cold pentane to give a dark green powder of the product P7 (2g, 2.9 mmol, 50%).Elemental analysis calculated for C. 35 H 37 F4FeN2O4: C, 61.68 H, 5.47; N, 4.11, found: C, 59.9; H 5.39; N 3.92. 1 H NMR (250 MHz, C6D6-50 μL THF-d825 °C) 62.91 (br s, 3H, p-Me), 50.93 (br s, 3H, p-Me), 28.92 (br s, 14H, o-Me and mH Ar), 20.99 (br s, 14H, Me and mH Ar), -25.10 (br s, 2H, CH) (deviations in integration values ​​may be observed due to signal width) EXAMPLE 8: Synthesis of P8

[0458] n-BuLi (2.5 M in hexane) (0.8 mL, 2.0 mmol) was added with stirring to a solution of (E)-N-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3,4,5,6-tetrafluoroaniline (0.77 g, 1.8 mmol) in THF (3.6 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 4 h at 25 °C. Then, FeBr2 (0.389 g, 1.8 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane or pentane and extracted with Et2O. The ethereal solution was filtered, concentrated and replaced with hexane. After adding a few drops of THF and cooling to -20°C, red crystals of the product P8 (0.63 g, 0.8 mmol, 44%) are obtained. 1 H NMR (250 MHz, C6D6-50 μL THF-d8, 25 °C) δ ppm 71.09 (s, 3H, p-Me), 33.98 (s, 3H, p-Me), 27.42 (br s, 8H, mH Ar and o-Me), 15.91 (s, 2H, mH Ar), 4.43 (br s, 14H, THF), 2.13 (br s, 6H, o-Me), 1.75 (br s, 14H, THF).7 Li NMR (117 MHz, C6D6-50μL THF-d8, 25 °C) δ ppm 162.66 (br s).

[0459] EXAMPLE 9: Synthesis according to Byers of phenylcycloheptane (reference example)

[0460] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to EtNMeLi (1.2 eq) and Byers catalyst (Angew. Chem., Int. Ed. 2020, 59, 5392) (10 mol%).

[0461] A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then made up to 0.08 M by adding benzene. The reaction mixture is stirred at 25 °C for 5 h, then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered, and evaporated under reduced pressure. Gas chromatographic analysis using dodecane as an internal standard gives phenylcycloheptane in 94% yield.

[0462] EXAMPLE 10: Synthesis A of phenylcycloheptane

[0463] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then made up to 0.08 M by adding benzene. The reaction mixture is stirred at 25 °C for 4 h, then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered, and evaporated under reduced pressure. Gas chromatographic analysis using dodecane as an internal standard gives phenylcycloheptane in >99% yield. Silica gel column chromatography is performed and gives phenylcycloheptane in 95% yield. 1H NMR (400 MHz, CDCl3. 25°C) (mixture with dodecane) δ ppm 7.30-7.14 (m, 5H), 2.70-2.65 (m, 1H), 1.95-1.92 (m, 2H), 1.83-1.60 (m, 10H). 13 C NMR (100 MHz, CDCl3, 25°C) (mixture with dodecane) δ 150.0, 128.3, 126.7, 125.5, 47.0, 36.8, 28.0, 27.2.

[0464] The yield is higher than that obtained with the Byers catalyst and the reaction is faster.

[0465] EXAMPLE 11: Synthesis B of phenylcycloheptane

[0466] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P6 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total bromocycloheptane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h (time not optimized) and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives phenylcycloheptane in >99% yield.

[0467] EXAMPLE 12: Synthesis C of phenylcycloheptane

[0468] The reaction is carried out under an inert atmosphere in a glove box. Catalyst P7 was previously exposed to ambient air for 2 weeks. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P7 (10 mol%) and EtNMeLi (2.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total bromocycloheptane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h (reaction time not optimized) and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives phenylcycloheptane in 89% yield. EXAMPLE 13: Synthesis D of phenylcycloheptane

[0469] The reaction is carried out under an inert atmosphere outside the glove box. Catalyst P7 was previously exposed to ambient air for 2 weeks. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P7 (10 mol%) and EtNMeLi (2.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total bromocycloheptane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives phenylcycloheptane in 87% yield.

[0470] This example shows that the catalyst is not sensitive to ambient air because it retains good catalytic activities even after being exposed to it for two weeks.

[0471] EXAMPLE 14: Synthesis E of phenylcycloheptane

[0472] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P8 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total bromocycloheptane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 5 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Gas chromatographic analysis using dodecane as an internal standard gives phenylcycloheptane in >99% yield.

[0473] The yield is higher than that obtained with the Byers catalyst and the reaction is faster.

[0474] EXAMPLE 15: Synthesis A of octylbenzene

[0475] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. A silica gel column chromatography is carried out and gives octylbenzene with 71% yield. 1H NMR (400 MHz, CDCl3, 25°C) δ ppm 7.29 (t, J= 7.4 Hz, 2H), 7.20 (d, J= 7.4 Hz, 3H), 2.63 (t, J= 7.8 Hz, 2H), 1.66-1.60 (m, 2H), 1.33-1.30 (m, 10H), 0.91 (t, J= 6.5 Hz, 3H). 13 C NMR (100 MHz, CDCl3, 25°C) δ ppm 143.0, 128.4, 128.2, 125.5, 36.0, 31.9, 31.5, 29.5, 29.4, 29.3, 22.7, 14.1.

[0476] EXAMPLE 16: Synthèse B de l'octylbenzene

[0477] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P7 (10 mol%) and EtNMeLi (2.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then made up to 0.08 M by adding benzene. The reaction mixture is stirred at 25 °C for 29 h, then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered, and evaporated under reduced pressure. A silica gel column chromatography is carried out and gives octylbenzene with 91% yield. 1 H NMR (400 MHz, CDCl3, 25°C) δ ppm 7.29 (t, J= 7.4 Hz, 2H), 7.20 (d, J= 7.4 Hz, 3H), 2.63 (t, J= 7.8 Hz, 2H), 1.66-1.60 (m, 2H), 1.33-1.30 (m, 10H), 0.91 (t, J= 6.5 Hz, 3H). 13C NMR (100 MHz, CDCl3, 25°C) δ ppm 143.0, 128.4, 128.2, 125.5, 36.0, 31.9, 31.5, 29.5, 29.4, 29.3, 22.7, 14.1.

[0478] EXAMPLE 17: Synthesis of 1-methyl-4-octylbenzene

[0479] The reaction is carried out under an inert atmosphere in a glove box. A solution of 4-tolylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1H NMR using 1,3,5-trimethoxybenzene as internal standard gives l-methyl-4-octylbenzene in 82% yield. Silica gel column chromatography is performed and gives l-methyl-4-octylbenzene in 76% yield. 1 H NMR (360 MHz, CDCI3, 25°C) δ ppm 7.15-7.10 (m, 4H), 2.61 (t, J= 7.6 Hz, 2H), 2.37 (s, 3H), 1.66-1.60 (m, 2H), 1.35-1.32 (m, 10H), 0.93 (t, J= 6.8 Hz, 3H). 13 C NMR (100 MHz, CDCl3, 25°C) δ ppm 139.9, 134.9, 128.9, 128.3, 35.5, 31.9, 31.7, 29.5, 29.4, 29.3, 22.7, 21.0, 14.1.

[0480] EXAMPLE 18: Synthesis of l-methoxy-4-octylbenzene

[0481] The reaction is carried out under an inert atmosphere in a glove box. A solution of 4-methoxyphenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h or 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 1-methoxy-4-octylbenzene in 78% yield (after 24 h) and 99% yield (after 48 h). Silica gel column chromatography is performed and gives 1-methoxy-4-octylbenzene in 76% yield (after 24 h). 1 H NMR (360 MHz, CDCl3, 25°C) δ ppm 7.12 (d, J= 8.7 Hz, 2H), 6.85 (d, J= 8.7 Hz, 2H), 3.81 (s, 3H), 2.57 (t, J= 7.6 Hz, 2H), 1.64-1.56 (m, 2H), 1.33-1.30 (m, 10H), 0.91 (t, J= 6.8 Hz, 3H). 13 C NMR (360 MHz, CDCl3, 25°C) δ ppm 157.6, 135.0, 129.2, 113.6, 55.2, 35.0, 31.9, 31.8, 29.5, 29.3, 22.7, 14.1. MS-HR (ESI) m / z calculated for C 15 H 25 O [M+H] + , 221.1900, found: 221.1756.

[0482] EXAMPLE 19: Synthesis of l-phenoxy-4-octylbenzene

[0483] The reaction is carried out under an inert atmosphere in a glove box. A solution of 4-phenoxyphenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives l-phenoxy-4-octylbenzene in >96% yield.

[0484] EXAMPLE 20: Synthesis of N^V-dimethyl-4-octylaniline

[0485] The reaction is carried out under an inert atmosphere in a glove box. A solution of 4-(dimethylamino)phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then made up to 0.08 M by adding benzene. The reaction mixture is stirred at 25 °C for 24 h, then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered, and evaporated under reduced pressure. A silica gel column chromatography is carried out and gives N,N-dimethyl-4-octylanilinc with

[0486] 90% yield. H NMR (360 MHz, CDCl3, 25°C) δ ppm 7.12 (d, J= 8.7 Hz, 2H), 6.75 (d, J= 8.7 Hz, 2H), 3.96 (s, 6H), 2.57 (t, J1, 6= 7.6), δ ppm. 7.3 Hz, 2H), 1.36–1.33 (m, 10H), 0.94 (t, J= 6.8 Hz, 3H). 13 C NMR (90 MHz, CDCl3, 25°C) δ ppm 148.9, 131.23, 128.90, 113.0, 40.9, 34.9, 31.9, 29.5, 29.3, 22.1.7., 14 MS-HR (ESI) m / z calculations for C 16 H 28 N [M+H] + 234.2216, found: 234.2213.

[0487] EXAMPLE 21 Synthesis of l-chloro-4-octylbenzene.

[0488] The reaction is carried out under an inert atmosphere in a glove box. A solution of 4-chlorophenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 80 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives l-chloro-4-octylbenzene in 40% yield.

[0489] EXAMPLE 22: Synthesis of l-nitro-4-octylbenzene

[0490] The reaction is carried out under an inert atmosphere in a glove box. A solution of 4-nitrophenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 80 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives l-nitro-4-octylbenzene in 36% yield.

[0491] EXAMPLE 23: Synthesis of l-fluoro-4-octylbenzene

[0492] The reaction is carried out under an inert atmosphere in a glove box. A solution of 4-fluorophenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then made up to 0.08 M by adding benzene. The reaction mixture is stirred at 25°C for 24 h, then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered, and evaporated under reduced pressure. Silica gel column chromatography is performed and gives l-fluoro-4-octylbenzene with 88% yield. 1 H NMR (360 MHz, CDCl3, 25°C) δ ppm 7.16-7.11 (m, 2H), 7.01-6.94 (m, 2H), 2.59 (t, J= 7.6 Hz, 2H), 1.61 (which, J= 7.4 Hz, 2H), 1.33-1.30 (m, 10H), 0.91 (t, J= 6.7 Hz, 3H). 13C NMR (90 MHz, CDCl3, 25°C) δ ppm 161.1 (d, J= 242.8 Hz), 138.5 (d, J= 3.2 Hz), 129.6 (d, J= 7.8 Hz), 114.9 (d, J= 20.8 Hz), 35.1, 31.9, 31.7, 29.5, 29.3, 29.2, 22.7, 14.1. EXAMPLE 24: Synthesis of l-octyl-3-(trifluoromethyl)benzene

[0493] The reaction is carried out under an inert atmosphere in a glove box. A solution of 3-trifluoromethylphenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography is performed and gives l-octyl-3-(trifluoromethyl)benzene with 83% yield. 1 H NMR (360 MHz, CDCI3, 25°C) δ ppm 7.46-7.34 (m, 4H), 2.67 (t, J= 7.6 Hz, 2H), 1.64 (qt, J= 7.4 Hz, 2H), 1.34-1.29 (m, 10H), 0.90 (t, J= 6.7 Hz, 3H). 13C RMN (90 MHz, CDCl3, 25°C) δ ppm 143.8, 131.8, 130.5 (q, J= 31.8 Hz), 128.9, 125.0 (q, J= 3.7 Hz), 124.3 (q, J= 271.8 Hz), 122.5 (q, J= 3.7 Hz), 35.8, 31.9, 31.3, 29.4, 29.2, 22.7, 14.1.

[0494] EXEMPLE 25 : Synthèse du benzyl 4-phenylpiperidine-l-carboxylate

[0495] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of benzyl 4-bromopiperidine-l -carboxylate (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total concentration of benzyl 4-bromopiperidine-l -carboxylate of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography is performed and gives benzyl 4-phenylpiperidine-1-carboxylate with 95% yield. 1H RMN (360 MHz, CDCI3, 25°C) δ ppm 7.45- 7.35 (m, 7H), 7.29-7.25 (m, 3H), 5.24 (s, 2H), 4.40 (s, 2H), 2.94 (s, 2H), 2.76-2.70 (m, 1H), 1.88 (m, 2H), 1.72-1.70 (m, 2H). 13 C RMN (90 MHz, CDCI3, 25°C) δ ppm 155.2, 145.4, 136.8, 128.4, 127.8, 126.6, 126.3, 67.0, 44.5, 42.5, 33.0. MS-HR (ESI) m / z calculé pour C 19 H 22 NO2[M+H] + 296.1645, trouvé: 296.1638.

[0496] EXEMPLE 26 : Synthèse A du 1-phényladamantane The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromoadamantane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total concentration of 1-chloroadamantane of 0.08 M. The reaction mixture is stirred at 80 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography is performed and gives 1-phenyladamantane with 98% yield. 1 H NMR (360 MHz, CDCl3, 25°C) δ ppm 7.41-7.32 (m, 4H), 7.23-7.18 (m, 1H), 2.13 (m, 3H), 1.96-1.95 (m, 6H), 1.85-1.75 (m, 6H). 13C NMR (90 MHz, CDCl3, 25°C) δ ppm 151.3, 128.1, 125.5, 124.8, 43.1, 36.8, 28.9.

[0497] EXAMPLE 27: Synthesis B of 1-phenyladamantane

[0498] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P7 (10 mol%) and EtNMeLi (2.2 eq). A solution of 1-bromoadamantane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total concentration of 1-chloroadamantane of 0.08 M. The reaction mixture is stirred at 80 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography is performed and gives 1-phenyladamantane with 79% yield.1 H RMN (360 MHz, CDCl3, 25°C) δ ppm 7.41-7.32 (m, 4H), 7.23-7.18 (m, 1H), 2.13 (m, 3H), 1.96-1.95 (m, 6H), 1.85-1.75 (m, 6H). 13 C RMN (90 MHz, CDCl3, 25°C) δ ppm 151.3, 128.1, 125.5, 124.8, 43.1, 36.8, 28.9.

[0499] EXEMPLE 28 : Synthèse du 2-octylthiophène

[0500] The reaction is carried out under an inert atmosphere in a glove box. A solution of 2-thienylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 2-octylthiophene in 78% yield. EXAMPLE 29: Synthesis of 6-cycloheptylquinoline

[0501] The reaction is carried out under an inert atmosphere in a glove box. A solution of 6-quinolineboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene. The reaction mixture is stirred at 80 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography is performed and gives 6-cycloheptylquinoline with 88% yield. 1H NMR (400 MHz, CDCI3, 25°C) δ ppm 8.88 (d, J= 4.2 Hz, 1H), 8.07 (d, J= 8.4 Hz, 1H), 8.02 (d, J= 8.6 Hz, 1H), 7.60-7.56 (m, 2H), 7.34 (dd, J= 4.2 Hz, J= 8.3 Hz, 1H), 2.85 (st, 1H), 2.02-1.95 (m, 2H), 1.87- 1.80 (m, 2H), 1.78-1.69 (m, 4H), 1.66-1.55 (m, 4H). 13 C NMR (100 MHz, CDCl3, 25°C) δ ppm 149.5, 148.1, 147.1, 135.6, 129.7, 129.3, 128.3, 124.0, 120.9, 46.8, 36.6, 27.9, 27.2. MS-HR (ESI) m / z calculated for C16H20N [M+H] + 226.1590, found: 226.1583.

[0502] EXAMPLE 30: Synthesis of Ll'-methylenedibenzene

[0503] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P6 (10 mol%) and EtNMeLi (1.2 eq). A solution of benzyl bromide (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total benzyl bromide concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives 1,r-methylenedibenzene in 30% yield.

[0504] EXAMPLE 31: Synthesis of 2-octylnaphthalene

[0505] The reaction is carried out under an inert atmosphere in a glove box. A solution of napthylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSCE, filtered and evaporated under reduced pressure. A silica gel column chromatography is carried out and gives 2-octylnaphthalene with 93% yield. 1H NMR (400 MHz, CDC13, 25°C) δ ppm 7.92-7.86 (m, 3H), 7.72 (s, 1H), 7.53 (quintet, J= 15.1 Hz, 6.8 Hz, 2H), 7.44 (d, J= 8.3 Hz, 1H), 2.88 (t, J= 7.7 Hz, 2H), 1.86-1.79 (m, 2H), 1.47-1.41 (m, 10H), 1.03 (t, J= 7.0 Hz, 3H). 13 C NMR (100 MHz, CDCl3, 25°C) δ ppm 140.4, 133.7, 132.0, 127.7, 127.6, 127.4, 127.4, 126.3, 125.8, 124.9, 36.1, 31.9, 31.4, 29.5, 29.4, 29.3, 22.7, 14.1.

[0506] EXEMPLE 32 : Synthèse de l'hexylbenzène

[0507] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromohexane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total 1-bromohexane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSCE, filtered and evaporated under reduced pressure. Silica gel column chromatography is carried out and gives hexylbenzene with 90% yield. 1 H NMR (360 MHz, CDCl3, 25°C) δ ppm 7.22-7.17 (m, 2H), 7.11-7.07 (m, 3H), 2.53 (t, J= 7.6 Hz, 2H), 1.58-1.49 (m, 2H), 1.28- 1.20 (m, 6H), 0.81 (t, J= 6.8 Hz, 3H). 13C NMR (90 MHz, CDCl3, 25°C) δ ppm 143.0, 128.4, 128.2, 125.5, 36.0, 31.7, 31.5, 29.0, 22.6, 14.1.

[0508] EXAMPLE 33: Synthesis A of cyclopropylbenzene

[0509] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocyclopropane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total bromocyclopropane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1H NMR using 1,3,5-trimethoxybenzene as internal standard gives cyclopropylbenzene in 45% yield.

[0510] EXAMPLE 34: Synthesis B of cyclopropylbenzene

[0511] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P6 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocyclopropane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total bromocyclopropane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1H NMR using 1,3,5-trimethoxybenzene as internal standard gives cyclopropylbenzene in 26% yield.

[0512] EXAMPLE 35: Synthesis of 3-phenyloxetane

[0513] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 3-bromooxetane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total 3-bromooxetane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 3-phenyloxetane in 69% yield. Silica gel column chromatography is performed and gives 3-phenyloxetane in 58% yield. 1 H NMR (360 MHz, CDCl3, 25°C) δ ppm 7.44-7.30 (m, 5H), 5.11 (dd, J= 8.4 Hz, J= 6.0 Hz, 2H), 4.82 (t, J= 6.4 Hz, 2H), 4.30-4.23 (m, 1H). 13 C NMR (90 MHz, CDCl3, 25°C) δ ppm 141.5, 128.8, 127.0, 126.8, 78.9, 40.4.

[0514] EXAMPLE 36: Synthesis A of tert-butylbenzene

[0515] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl chloride (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total tert-butyl chloride concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives tert-butylbenzene in 54% yield.

[0516] EXAMPLE 37: Synthesis B of tert-butylbenzene

[0517] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P6 (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl chloride (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total tert-butyl chloride concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives tert-butylbenzene in 32% yield.

[0518] EXAMPLE 38: Synthesis of 2-cycloheptylthiophene

[0519] The reaction is carried out under an inert atmosphere in a glove box. A solution of 2-thienylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total bromocycloheptane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 2-cycloheptylthiophene in 86% yield. Silica gel column chromatography is performed and gives 2-cycloheptylthiophene in 78% yield. 1H NMR (250 MHz, CDCl3, 25°C) δ ppm 7.10 (dd, J = 5.0 Hz, 1.0 Hz, 1H), 6.91 (dd, J = 5.0 Hz, 3.5 Hz, 1H), 6.80 (d, J = 3.1 Hz, 1H), 3.04 (septet, J = 4.1 Hz, 1H), 2.11-2.05 (m, 2H), 1.79-1.55 (m, 10H). 13 C NMR (63 MHz, CDCl3, 25°C) δ ppm 153.6, 126.3, 122.0, 121.7, 41.6, 37.5, 28.1, 26.3.

[0520] EXEMPLE 39 : Synthèse du tert-butyl 4-(5-cvcloheptylpyridin-2-yl)piperazine-l-carboxylate

[0521] The reaction is carried out under an inert atmosphere in a glove box. A solution of l-tert-butyl-4-(pyridin-2-yl)piperazineboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then made up to 0.08 M by adding benzene. The reaction mixture is stirred at 25 °C for 24 h, then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered, and evaporated under reduced pressure. Silica gel column chromatography is performed and gives tert-butyl 4-(5-cycloheptylpyridin-2-yl)piperazine-l-carboxylate with 92% yield. 1H NMR (360 MHz, CDCl3, 25 °C) δ ppm 7.96 (d, J= 2.3 Hz, 1H), 7.28 (dd, J= 2.4 Hz, 8.7 Hz, 1H), 6.53 (d, J= 8.7 Hz, 1H), 3.48- 3.45 (m, 4H), 3.40-3.37 (m, 4H), 2.54-2.46 (m, 1H), 1.81-1.48 (m, 12H), 1.41 (s, 9H). 13 C NMR (90 MHz, CDCl3, 25 °C) δ ppm 157.8, 154.8, 145.9, 136.1, 134.9, 107.3, 79.8, 45.5, 43.4, 36.7, 28.4, 27.8, 26.9. MS-HR (ESI) m / z calculated for C 21 H 34 N3O2[M+H] + 360.2646, found: 360.2629.

[0522] EXAMPLE 40: Synthesis of tert-butyldimethyl(3-phenylpropoxy)silane The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of (4-bromobutoxy)(tert-butyl)dimethylsilane (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then made up to benzene to obtain a total concentration of (4-bromobutoxy)(tert-butyl)dimethylsilane of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography is performed and gives tert-butyldimethyl(3-phenylpropoxy)silane with 78% yield. 1H RMN (360 MHz, CDCl3. 25°C) δ ppm 7.33- 7.29 (m, 2H), 7.24- 7.19 (m, 3H), 3.67 (t, J= 6.3 Hz, 2H), 2.72 (t, J= 7.8 Hz, 2H), 1.92-1.84 (m, 2H), 0.95 (s, 9H), 0.09 (s, 6H). 13 C RMN (90 MHz, CDCl3, 25°C) δ ppm 142.3, 128.5, 128.31, 125.7, 62.4, 34.5, 32.2, 26.0, 18.4, -5.2.

[0523] EXEMPLE 41 : Synthèse A du cyclopentylbenzène

[0524] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocyclopentane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total bromocyclopentane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives cyclopentylbenzene in 99% yield. Silica gel column chromatography is performed and gives cyclopentylbenzene in 70% yield. 1H RMN (360 MHz, CDCl3, 25°C) δ ppm 7.21- 7.14 (m, 4H), 7.09- 7.05 (m, 1H), 2.94-2.85 (m, 1H), 2.01-1.94 (m, 2H), 1.77-1.66 (m, 2H), 1.64-1.45 (m, 4H). 13 C RMN (90 MHz, CDCl3, 25°C) δ ppm 146.5, 128.2, 127.1, 125.6, 45.9, 34.6, 25.5.

[0525] EXEMPLE 42 : Synthèse B du cyclopentylbenzène

[0526] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of chlorocyclopentane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total bromocyclopentane concentration of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives cyclopentylbenzene in 99% yield. 1 H NMR (360 MHz, CDCl3, 25°C) δ ppm 7.21- 7.14 (m, 4H), 7.09- 7.05 (m, 1H), 2.94-2.85 (m, 1H), 2.01-1.94 (m, 2H), 1.77-1.66 (m, 2H), 1.64-1.45 (m, 4H). 13C NMR (90 MHz, CDCl3, 25°C) δ ppm 146.5, 128.2, 127.1, 125.6, 45.9, 34.6, 25.5.

[0527] EXAMPLE 43: Synthesis C of cyclopentylbenzene

[0528] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of iodocyclopentane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M iodocyclopentane concentration by adding benzene. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard gives cyclopentylbenzene in 77% yield. Silica gel column chromatography is performed and gives cyclopentylbenzene in 77% yield.

[0529] P5 can catalyze carbon-carbon bond formation with previously defined brominated, chlorinated or iodinated halogenated derivatives Z-Hal.

[0530] EXAMPLE 44: Synthesis of tert-butyl 3-phenylazetidine-l-carboxylate

[0531] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl 3-bromoazetidine-1-carboxylate (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to the required concentration by adding benzene to obtain a total concentration of tert-butyl 3-bromoazetidine-1-carboxylate of 0.08 M. The reaction mixture is stirred at 25 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard gives tert-butyl 3-phenylazetidine-1-carboxylate in >99% yield. Silica gel column chromatography is performed and gives tert-butyl 3-phenylazetidine-1-carboxylate in 83% yield. 1 H NMR (360 MHz, CDCl3, 25°C) δ ppm 7.30-7.15 (m, 5H), 4.25 (t, J= 8.7 Hz, 2H), 3.90 (dd, J= 8.6 Hz, J= 6.1 Hz, 2H), 3.69-3.61 (m, 1H), 1.39 (s, 9H). 13 C NMR (90 MHz, CDCl3, 25°C) δ ppm 156.4, 142.2, 128.7, 126.9, 126.7, 79.5, 33.5, 28.4. MS-HR (ESI) m / z calculated for C 14 H 20 NO2[M+H] + 234.1489, found: 234.1482.

[0532] EXAMPLE 45: Synthesis of 2-octyl-l-tosyl-lH-indole

[0533] The reaction is carried out under an inert atmosphere in a glove box. A solution of (1-tosyl-1H-indol-2-yl)boronic acid pinacolic ester_(2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4. filtered and evaporated under reduced pressure. Silica gel column chromatography is performed and gives 2-octyl-l-tosyl-1H-indole with 69% yield. 1H NMR (360 MHz, CDCl3, 25 °C) δ ppm 7.90 (d, J= 8.5 Hz, 1H), 7.77 (d, J= 8.4 Hz, 2H), 7.53 (d, J= 3.7 Hz, 1H), 7.32 (d, J= 1.0 Hz, 1H), 7.20 (d, J= 8.1 Hz, 2H), 7.14 (dd, J= 8.5 Hz, 1.6 Hz, 1H), 6.60 (dd, J= 3.6 Hz, 0.4 Hz, 1H), 2.66 (t, J= 7.6 Hz, 2H), 2.32 (s, 3H), 1.62 (quint, J= 7.2 Hz, 2H), 1.31-1.27 (m, 10H), 0.89 (t, J= 7.0 Hz, 3H). 13 C NMR (90 MHz, CDCl3, 25 °C) δ ppm 144.9, 138.2, 135.6, 133.4, 131.1, 129.9, 126.9, 126.5, 125.5, 120.7, 113.3, 109.0, 35.9, 32.0, 29.6, 29.5, 29.4, 22.8, 21.6, 14.2.

[0534] EXEMPLE 46 : Synthèse du ti / 7-butyl 2-octyl-lH-indole-l-carboxylate

[0535] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid_(2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol %) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 80 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard gives tert-butyl 2-octyl-1H-indole-1-carboxylate in 82% yield. Silica gel column chromatography is performed and gives tert-butyl 2-octyl-1H-indole-1-carboxylate in 50% yield. 1 H NMR (300 MHz, CDCI3, 25°C) δ ppm 8.02 (d, J= 8.3 Hz, 1H), 7.56 (d, J= 3.6 Hz, 1H), 7.35 (d, J= 1.0 Hz, 1H), 7.14 (dd, J= 8.5 Hz, 1.7 Hz, 1H), 6.51 (dd, J= 3.7 Hz, 0.6 Hz, 1H), 2.69 (t, J= 7.5 Hz, 2H), 1.67 (s, 9H), 1.64-1.60 (m, 2H), 1.32-1.26 (m, 10H), 0.88 (t, J= 6.8 Hz, 3H). 13 C NMR (75 MHz, CDCI3, 25°C) δ ppm 149.9, 137.3, 133.5, 130.7, 125.9, 125.0, 120.2, 114.7, 107.1, 83.4, 35.8, 32.0, 31.9, 29.5, 29.3, 28.2, 22.7, 14.1. MS-HR (ESI) m / z calculated for C25H25F4N2 [M+H] + 330.2428, found: 330.2415.

[0536] EXAMPLE 47: Synthesis of 2-octyl-l-benzofuran

[0537] The reaction is carried out under an inert atmosphere in a glove box. A solution of 2-benzofuranboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 80 °C for 48 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 2-octyl-l-benzofuran in 87% yield. Silica gel column chromatography is performed and gives 2-octyl-l-benzofuran in 82% yield. 1H RMN (400 MHz, CDCI3, 25°C) δ ppm 7.49-7.47 (m, 1H), 7.41 (d, J= 7.9 Hz, 1H), 7.22-7.15 (m, 2H), 6.37 (s, 1H), 2.76 (t, J= 7.6 Hz, 2H), 1.75 (qui, J= 7.6 Hz, 2H), 1.39-1.28 (m, 10H), 0.89 (t, J= 7.1 Hz, 3H). 13 C RMN (100 MHz, CDCl3, 25°C) δ ppm 160.0, 154.6, 129.0, 123.0, 122.3, 120.1, 110.7, 101.7, 31.8, 29.3, 29.2, 28.5, 27.7, 22.7, 14.1

[0538] EXEMPLE 48 : Synthèse du 3-octylfurane

[0539] The reaction is carried out under an inert atmosphere in a glove box. A solution of 3-furaneboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 3-octylfuran in 89% yield. Silica gel column chromatography is performed and gives 3-octylfuran in 82% yield. 1H NMR (300 MHz, CDCl3, 25 °C) δ ppm 7.35 (br s, 1H), 7.21 (br s, 1H), 6.27 (br s, 1H), 2.41 (t, J= 7.5 Hz, 2H), 1.58-1.53 ​​(m, 2H), 1.31-1.29 (m, 10H), 0.90 (t, J= 6.5 Hz, 3H). 13 C NMR (75 MHz, CDCl3, 25 °C) δ ppm 142.7, 138.8, 125.5, 111.2, 32.0, 30.2, 29.6, 29.5, 29.4, 24.9, 22.8, 14.2.

[0540] EXEMPLE 49 : Synthèse du (3-méthylundécyl)benzène

[0541] The reaction is carried out under an inert atmosphere in a glove box. A solution of 9-octyl-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (20 mol%) and NMe2Li (1.2 eq). A solution of (3-bromobutyl)benzene (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to the total concentration of (3-bromobutyl)benzene of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc (3 x 40 mL), the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Gas chromatographic analysis using dodecane as an internal standard gives (3-methylundecyl)benzene in 89% yield. Silica gel column chromatography is performed and gives (3-methylundecyl)benzene in 60% yield. 1H RMN (300 MHz, CDCl3. 25°C) δ ppm 7.34-7.29 (m, 2H), 7.23-7.21 (m, 3H), 2.74-2.64 (m, 1H), 2.63-2.55 (m, 1H), 1.71-1.61 (m, 1H), 1.50-1.46 (m, 2H), 1.30 (br s, 13H), 1.19-1.14 (m, 1H), 0.97-0.90 (m, 6H). 13 C RMN (75 MHz, CDCl3, 25°C) δ ppm 143.4, 128.5, 128.4, 125.6, 39.1, 37.1, 33.7, 32.7, 32.1, 30.2, 29.8, 29.5, 27.1, 22.9, 19.8, 14.3.

[0542] EXEMPLE 50 : Synthèse du benzyl 4-(3-phenylpropyl)piperidine-l-carboxylate

[0543] The reaction is carried out under an inert atmosphere in a glove box. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane_(2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (20 mol%) and NMe2Li (1.2 eq). A solution of benzyl 4-bromopiperidine-l -carboxylate (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total concentration of benzyl 4-bromopiperidine-l -carboxylate of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4. filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives benzyl 4-(3-phenylpropyl)piperidine-l-carboxylate in 70% yield.

[0544] EXAMPLE 51: Synthesis of tert-butyldimethyl((6-phenylhexyl)oxy)silane

[0545] The reaction is carried out under an inert atmosphere in a glove box. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (20 mol %) and NMe2Li (1.2 eq). A solution of (4-bromobutoxy)(tert-butyl)dimethylsilane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total concentration of (4-bromobutoxy)(tert-butyl)dimethylsilane of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard gives tert-butyldimethyl((6-phenylhexyl)oxy)silane in 78% yield. Silica gel column chromatography is performed and gives tert-butyldimethyl((6-phenylhexyl)oxy)silane in 44% yield. 1 H NMR (250 MHz, CDCl3, 25°C) δ ppm 7.34-7.29 (m, 2H), 7.23-7.18 (m, 3H), 3.63 (t, J= 6.4 Hz, 2H), 2.64 (t, J= 7.5 Hz, 2H), 1.69-1.50 (m, 4H), 1.42- 1.36 (m, 4H), 0.93 (s, 9H), 0.08(m, 6H). 13 C NMR (63 MHz, CDCl3, 25°C) δ ppm 143.0, 128.5, 128.4, 125.7, 63.4, 36.1, 33.0, 31.6, 29.3, 26.1, 25.8, 18.5, -5.1.

[0546] EXAMPLE 52: Synthesis of (3-cyclopentylpropyl)benzene

[0547] The reaction is carried out under an inert atmosphere in a glove box. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (20 mol%) and NMe2Li (1.2 eq). A solution of bromocyclopentane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total bromocyclopentane concentration of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives (3-cyclopentylpropyl)benzene in 59% yield. Silica gel column chromatography is performed and gives (3-cyclopentylpropyl)benzene in 53% yield. 1H NMR (250 MHz, CDCl3, 25 °C) δ ppm 7.35-7.30 (m, 2H), 7.24-7.22 (m, 3H), 2.65 (t, J= 7.6 Hz, 2H), 1.83-1.78 (m, 3H), 1.71-1.57 (m, 6H), 1.44-1.38 (m, 2H), 1.12-1.11 (m, 2H). 13 C RMN (63 MHz, CDCl3, 25°C) δ ppm 143.1, 128.5, 128.4, 125.7, 40.2, 36.4, 36.1, 32.8, 30.8, 25.4.

[0548] EXEMPLE 53 : Synthèse du (3-phenylpropyl)cvcloheptane

[0549] The reaction is carried out under an inert atmosphere in a glove box. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (20 mol%) and NMe2Li (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total bromocycloheptane concentration of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives (3-phenylpropyl)cycloheptane in 74% yield. Silica gel column chromatography is performed and gives (3-phenylpropyl)cycloheptane in 65% yield. 1H NMR (360 MHz, CDCl3, 25 °C) δ ppm 7.31-7.26 (m, 2H), 7.21-7.17 (m, 3H), 2.60 (t, J= 7.8 Hz, 2H), 1.73-1.57 (m, 8H), 1.50-1.37 (m, 5H), 1.32-1.27 (m, 2H), 1.18 (dtd, J= 2.7 Hz, 9.9 Hz, 12.3 Hz, 2H). 13 C NMR (63 MHz, CDCl3, 25°C) δ ppm 143.1, 128.5, 128.4, 125.7, 39.4, 38.1, 36.5, 34.8, 29.5, 28.7, 26.7.

[0550] EXEMPLE 54 : Synthèse du l-méthyl-2-octylbenzène

[0551] The reaction is carried out under an inert atmosphere in a glove box. A solution of 2-tolylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 40 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives l-methyl-2-octylbenzene in 99% yield. Silica gel column chromatography is performed and gives l-methyl-2-octylbenzene in 90% yield. 1H NMR (360 MHz, CDCI3, 25 °C) δ ppm 7.18-7.13 (m, 4H), 2.64 (t, J= 7.6 Hz, 2H), 2.36 (s, 3H), 1.66-1.58 (m, 2H), 1.38-1.34 (m, 10H), 0.94 (t, J= 6.2 Hz, 3H). 13 C NMR (90 MHz, CDCl3, 25 °C) δ ppm 141.3, 135.9, 130.2, 128.9, 126.0, 125.8, 33.5, 32.1, 30.5, 29.9, 29.7, 29.5, 22.8, 19.4, 14.3.

[0552] EXEMPLE 55 : Synthèse du l-méthyl-3-octylbenzène

[0553] The reaction is carried out under an inert atmosphere in a glove box. A solution of 3-tolylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives l-methyl-3-octylbenzene in 99% yield. Silica gel column chromatography is performed and gives l-methyl-3-octylbenzene in 94% yield. 1H NMR (300 MHz, CDCl3, 25 °C) δ 7.20 (dd, J= 7.6 Hz, 7.6 Hz, 1H), 7.04-7.01 (m, 3H), 2.61 (t, J= 7.6 Hz, 2H), 2.37 (s, 3H), 1.67-1.65 (m, 2H), 1.35-1.32 (m, 10H), 0.93 (t, J= 6.5 Hz, 3H). 13 C NMR (75 MHz, CDCl3, 25 °C) δ ppm 143.0, 137.8, 129.4, 128.3, 126.4, 125.6, 36.1, 32.1, 31.8, 29.7, 29.6, 29.5, 22.9, 21.5, 14.3.

[0554] EXEMPLE 56 : Synthesis of 4-octylbenzoate de tert-butyle

[0555] The reaction is carried out under an inert atmosphere in a glove box. A solution of 4-(tert-butoxycarbonyl)phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 40 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives tert-butyl 4-octylbenzoate in 99% yield. Silica gel column chromatography is performed and gives tert-butyl 4-octylbenzoate in 82% yield. 1H NMR (360 MHz, CDCl3. 25 °C) δ ppm 7.91 (d, J= 7.7 Hz, 2H), 7.22 (d, J= 7.7 Hz, 2H), 2.65 (t, J= 7.6 Hz, 2H), 1.59 (br s, 9H + 2H), 1.30- 1.27 (m, 10H), 0.93 (t, J= 5.9 Hz, 3H). 13 C NMR (90 MHz, CDCl3, 25 °C) δ ppm 166.0, 148.0, 129.64, 129.58, 128.4, 80.7, 36.1, 32.0, 31.3, 29.6, 29.4, 28.4, 22.8, 14.2. MS-HR (ESI) m / z calculated for C 19 H 30 NaO2[M+Na] + 313.2127, found: 313.2138.

[0556] EXAMPLE 57: Synthesis of tert-butyl 3-(4-fluorophenyl)azetidine-l-carboxylate

[0557] The reaction is carried out under an inert atmosphere in a glove box. A solution of p-fluoroboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl 3-bromoazetidine-1-carboxylate (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total concentration of tert-butyl 3-bromoazetidine-1-carboxylate of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard gives tert-butyl 3-(4-fluorophenyl)azetidine-l-carboxylate in 92% yield. Silica gel column chromatography is performed and gives 3-(4-fluorophenyl)azetidine-l-carboxylate in 83% yield. 1 H NMR (400 MHz, CDCl3, 25 °C) δ ppm 7.34-7.31 (m, 2H), 7.11-7-06 (m, 2H), 4.38 (t, J= 8.7 Hz, 2H), 3.99 (dd, J= 6.0 Hz, 8.7 Hz, 2H), 3.76 (tt, J= 6.0 Hz, 8.7 Hz, 1H), 1.53 (s, 9H). 13 C NMR (100 MHz, CDCl3, 25 °C) δ ppm 161.9 (d, J= 245.4 Hz), 156.5, 138.1 (d, J= 3.1 Hz), 128.4 (d, J= 7.9 Hz), 115.6 (d, J= 21.3 Hz), 79.7, 56.8, 33.0, 28.5.

[0558] EXAMPLE 58: Synthesis of tert-butyl 3-(4-ethoxyphenyl)azetidine-l-carboxylate

[0559] The reaction is carried out under an inert atmosphere in a glove box. A solution of p-ethoxyboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl 3-bromoazetidine-1-carboxylate (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total concentration of tert-butyl 3-bromoazetidine-1-carboxylate of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard gives tert-butyl 3-(4-ethoxyphenyl)azetidine-l-carboxylate in 87% yield. Silica gel column chromatography is performed and gives 3-(4-ethoxyphenyl)azetidine-l-carboxylate in 78% yield. 1 H NMR (300 MHz, CDCl3, 25 °C) δ ppm 7.22-7.19 (m, 2H), 6.88-6.85 (m, 2H), 4.29 (t, J= 8.7 Hz, 2H), 4.02 (q, J= 7.0 Hz, 2H), 3.93 (dd, J= 6.0 Hz, 8.6 Hz, 2H), 3.67 (tt, J= 6.0 Hz, 8.6 Hz, 1H), 1.46 (s, 9H), 1.40 (t, J= 7.0 Hz, 3H). 13 C NMR (100 MHz, CDCl3, 25 °C) δ ppm 158.1, 156.5, 134.3, 127.9, 114.8, 79.5, 63.6, 56.9, 33.0, 28.5, 14.9.

[0560] EXAMPLE 59: Synthesis of l-cyclopentyl-2-(trifluoromethyl)benzene

[0561] The reaction is carried out under an inert atmosphere in a glove box. A solution of 2-trifluoromethylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocyclopentane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to 0.08 M by adding benzene to obtain a total bromocyclopentane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives l-cyclopentyl-2-(trifluoromethyl)benzene in 51% yield.

[0562] EXAMPLE 60: Synthesis of 2-phenyl-2,3-dihydro-1H-indene

[0563] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 2-bromo-2,3-dihydro-1H-indene (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total concentration of 2-bromo-2,3-dihydro-1H-indene of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 2-phenyl-2,3-dihydro-1H-indene in >99% yield. Silica gel column chromatography is performed and gives 2-phenyl-2,3-dihydro-1H-indene in 92% yield.1 H NMR (400 MHz, CDCl3, 25 °C) δ ppm 7.36-7.34 (m, 4H), 7.30-7.25 (m, 3H), 7.24-7.21 (m, 2H), 3.78-3.69 (m, 1H), 3.39 (dd, J= 8.1 Hz, 15.3 Hz, 2H), 3.13 (dd, J= 9.0 Hz, 15.4 Hz, 2H). 13 C NMR (100 MHz, CDCI3, 25 °C) δ ppm 145.6, 143.1, 128.6, 127.2, 126.6, 126.3, 124.4, 45.6, 41.0.

[0564] EXEMPLE 61 : Synthèse du N,N,5-triphénylhexanamide

[0565] The reaction is carried out under an inert atmosphere in a glove box. A solution of phenylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 5-bromo-N,N-diphenylhexanamide (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total concentration of 5-bromo-N,N-diphenylhexanamide of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives N,N,5-triphenylhexanamide in 93% yield. Silica gel column chromatography is performed and gives N,N.5-triphenylhexanamide in 84% yield. 1H NMR (300 MHz, CDCl3, 25 °C) δ ppm 7.40-7.17 (m, 15H), 2.72-2.65 (m, 1H), 2.27 (t, J= 6.6 Hz, 2H), 1.70-1.57 (m, 4H), 1.27 (d, J= 7.0 Hz, 3H). 13 C NMR (75 MHz, CDCI3, 25 °C) δ ppm 173.1, 147.5, 143.0, 129.4 (br), 128.4, 127.1, 126.0, 40.0, 38.0, 35.5, 23.8, 22.3. MS-HR (ESI) m / z calculé pour C 24 H 26 NO [M+H] + 344.2000, trouvé: 344.2009.

[0566] EXEMPLE 62 : Synthèse du l-methyl-5-octyl- 1H-pyrazole

[0567] The reaction is carried out under an inert atmosphere in a glove box. A solution of (1-methyl-1H-pyrazol-5-yl)boronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives l-methyl-5-octyl- \H-pyrazole in 15% yield.

[0568] EXAMPLE 63: Synthesis of 5-octylbenzo[d][l,31dioxole

[0569] The reaction is carried out under an inert atmosphere in a glove box. A solution of benzo[d][l,3]dioxol-5-ylboronic acid pinacolic ester (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 80°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 5-octylbenzo[d][l,3]dioxole in >99% yield. Silica gel column chromatography is performed and gives 5-octylbenzo[d][l,3]dioxole in 91% yield. 1H NMR (400 MHz, CDCl3, 25 °C) δ ppm 6.73 (d, J= 7.9 Hz, 1H), 6.69 (d, J= 1.4 Hz, 1H), 6.63 (dd, J= 1.4 Hz, 7.9 Hz, 1H), 5.92 (s, 2H), 2.53 (t, J= 7.6 Hz, 2H), 1.60-1.55 (m, 2H), 1.32-1.28 (m, 10H), 0.90 (t, J= 7.0 Hz, 3H). 13 C NMR (63 MHz, CDCI3, 25 °C) δ ppm 147.6, 145.5, 137.0, 121.2, 109.0, 108.1, 100.8, 35.9, 32.0, 31.9, 29.6, 29.41, 29.36, 22.8, 14.2.

[0570] EXEMPLE 64 : Synthèse du 2-octyl-2,3-dihydro-1H-indène The reaction is carried out under an inert atmosphere in a glove box. A solution of 9-octyl-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (20 mol%) and NMe2Li (1.2 eq). A solution of 2-bromo-2,3-dihydro-1H-indene (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to the total concentration of 2-bromo-2,3-dihydro-1H-indene of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. An analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 2-octyl-2,3-dihydro-1H-indene in 37% yield. Silica gel column chromatography is performed and gives 2-octyl-2,3-dihydro-1H-indene in 30% yield. 1<h2 style=";text-align:left;direction:ltr">H NMR (400 MHz, CDCl3, 25 °C) δ ppm 7.22-7.19 (m, 2H), 7.15-7.13 (m, 2 H), 3.06 (dd, J= 8.0 Hz, 15.4 Hz, 2H), 2.60 (dd, J= 8.2 Hz, 15.3 Hz, 2H), 2.45 (tt, J= 7.3 Hz, 14.7 Hz, 22.8 Hz, 1H), 1.41-1.29 (m, 14H), 0.92 (t, J= 7.0 Hz, 3H).<h2 style=";text-align:left;direction:ltr"> 13 <h2 style=";text-align:left;direction:ltr"> C RMN (100 MHz, CDCl3, 25°C) δ ppm 143.9, 126.1, 124.5, 40.4, 39.5, 36.0, 32.1, 30.0, 29.8, 29.5, 28.6, 22.8, 14.3.<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0571] <h2 style=";text-align:left;direction:ltr"> EXEMPLE 65: Synthesis of (3-methylhexane-l,6-diyl)dibenzene<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0572] The reaction is carried out under an inert atmosphere in a glove box. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (20 mol%) and NMe2Li (1.2 eq). A solution of (3-bromobutyl)benzene (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up by the addition of benzene to obtain a total concentration of (3-bromobutyl)benzene of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. A silica gel column chromatography is carried out and gives (3-methylhexane-l,6-diyl)dibenzene with 56% yield. 1H NMR (400 MHz, CDCl3, 25 °C) δ ppm 7.21-7.17 (m, 4H), 7.10-7.08 (m, 6H), 2.59-2.45 (m, 4H), 1.61-1.50 (m, 3H), 1.41-1.28 (m, 3H), 1.16-1.12 (m, 1H), 0.86 (d, J= 6.4 Hz, 3H). 13 C RMN (100 MHz, CDCl3, 25°C) δ ppm 143.2, 143.0, 128.54, 128.49, 128.4, 125.8, 125.7, 39.0, 36.7, 36.4, 33.6, 32.5, 29.1, 19.7.

[0573] EXEMPLE 66 : Synthèse du 5-méthyl- N,N-diphényltridecanamide

[0574] The reaction is carried out under an inert atmosphere in a glove box. A solution of 9-octyl-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (20 mol%) and NMe2Li (1.2 eq). A solution of 5-bromo-N,N-diphenylhexanamide (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to benzene to obtain a total concentration of 5-bromo-N,N-diphenylhexanamide of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 5-methylN,N-diphenyltridecanamide in 60% yield. Silica gel column chromatography is performed and gives 5-methylN,N-diphenyltridecanamide in 36% yield.1 H NMR (400 MHz, CDC13, 25 °C) δ ppm 7.39-7.37 (m, 4H), 7.30-7.28 (m, 6H), 2.27 (t, J= 7.6 Hz, 2H), 1.74-1.62 (m, 2H), 1.33-1.29 (m, 15H), 1.12-1.07 (m, 2H), 0.91 (t, J= 7.0 Hz, 3H), 0.85 (d, J= 6.5 Hz, 3H). 13 C RMN (100 MHz, CDC13, 25°C) δ ppm 173.4, 143.2, 129.4, 127.2 (br s), 37.0, 36.8, 35.8, 32.8, 32.1, 30.1, 29.8, 29.5, 27.2, 23.3, 22.8, 19.7, 14.2. MS-HR (ESI) m / z calculé pour C 26 H 38 NO [M+H] + 380.2932, trouvé: 380.2948. EXEMPLE 67 : Synthèse du (3-cvclopropylpropyl)benzène

[0575] The reaction is carried out under an inert atmosphere in a glove box. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) is added to the catalyst P5 (20 mol%) and NMe2Li (1.2 eq). A solution of bromocyclopropane (1 eq) in benzene (c = 0.25 M) is added to the solution which is then made up to the total bromocyclopropane concentration of 0.08 M. The reaction mixture is stirred at 25°C for 24 h and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives (3-cyclopropylpropyl)benzene in 30% yield.

[0576] EXAMPLE 68: Synthesis F of phenylcycloheptane

[0577] The reaction is carried out under an inert atmosphere in a glove box. A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the catalyst P5 (10 mol%). A solution of phenylmagnesium bromide (1.2 eq) in benzene (c = 0.5 M) is added to the solution which is then made up to the required concentration by adding benzene to obtain a total bromocycloheptane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h (time not optimized) and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Analysis by 1 H NMR using 1,3,5-trimethoxybenzene as internal standard gives phenylcycloheptane in >99% yield.

Claims

DEMANDS 1. Use of at least one of the compounds with the following general formula (I): in which: • A is chosen from: ▪ a -X group in which X is chosen from a chlorine atom and a bromine atom ▪ a group in which: M is a coordinating solvent; p is chosen from 1, 2, 3, 4, or a decimal number that can vary from a value greater than 0 but less than 4; a group • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is selected from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms as catalysts for coupling reactions. Use, according to claim 1, as catalysts for carrying out a reaction selected from carbon-carbon bond-forming reactions, using an organoboron, organomagnesium, organozinc, or organostanneal compound, in particular for carrying out the Suzuki-Miyaura reaction. Use, according to claim 1, for carrying out the Suzuki-Miyaura, Kumada, and Sonogashira reactions, in particular for carrying out the Suzuki-Miyaura reaction. Use, according to any one of claims 1 to 3, of at least one of the compounds having the following general formula (I): in which: A is chosen from: a group -X in which X is chosen from o a chlorine atom o a bromine atom a group in which: M is a coordinating solvent; p is chosen from 1, 2, 3, 4, or a decimal number that can vary from a value greater than 0 but less than 4; a group • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • when A corresponds to the grouping then R1, R5, R6, and R 10The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1, 2, or 4 to 10 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atom(s), or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and R2, R3, R4, R7, R8, and R9. are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • when A corresponds to the grouping -X or to the grouping then R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, the compound with the following formula being excluded:

5. Use, according to any one of claims 1 to 4, of at least one of the compounds of the following general formula (la): in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 10 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

6. Use, according to any one of claims 1 to 4, of at least one of the compounds of the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

7. Use, according to any one of claims 1 to 4, of at least one of the compounds having the following general formula: in which: • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

8. Use, according to any one of claims 1 to 5, of at least one of the compounds, > of the following general formula: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others. • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, with at least one of the groups B, C, D, or E being different from the others • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: ▪ R1 is different from R5 and / or R2 is different from R4 and ▪ R6 is identical to R 10 and R7 is identical to R9 or ▪ R6 is different from R 10 and / or R7 is different from R9 and ▪ R1 is identical to R5 and R2 is identical to R4 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, with at least one of the groups B, C, D, or E being different from the others • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5, R2 is identical to R4, and R6 is identical to R 10 R7 is identical to R9 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is either identical to R9 or R6 is different from R 10 and / or R7 is either different from R9 and R1, or identical to R5 and R2, or identical to R4 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5, R2 is identical to R4, and R6 is identical to R 10 R7 is identical to R9 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

9. Use, according to any one of claims 1 to 4 or 6, of at least one of the compounds, > of the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others. • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D, or E being different from the others • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: ▪ R1 is different from R5 and / or R2 is different from R4 and ▪ R6 is identical to R 10 and R7 is identical to R9 or ▪ R6 is different from R 10 and / or R7 is different from R9 and ▪ R1 is identical to R5 and R2 is identical to R4 • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D, or E being different from the others • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5, R2 is identical to R4, and R6 is identical to R 10 R7 is identical to R9 G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9 • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is either identical to R9 or R6 is different from R 10 and / or R7 is different from R9 and R1 is identical to R5 and R2 is identical to R4 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5, R2 is identical to R4, and R6 is identical to R 10 R? is identical to R9 • G is selected from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the coupling reactions. Use, according to any one of claims 1 to 4 or 7, of at least one of the compounds > of the following general formula: in which: • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, with at least one of the groups B, C, D, or E being different from the others • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9 G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, with at least one of the groups B, C, D, or E being different from the others • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is either identical to R9 or R6 is different from R 10 and / or R7 is either different from R9 and R1, or identical to R5 and R2, or identical to R4 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, with at least one of the groups B, C, D, or E being different from the others • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5, R2 is identical to R4, and R6 is identical to R 10 R7 is identical to R9 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is either identical to R9 or R6 is different from R 10 and / or R7 is either different from R9 and R1, or identical to R5 and R2, or identical to R4 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5, R2 is identical to R4, and R6 is identical to R 10 R7 is identical to R9 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

11. Use, according to any one of claims 1 to 8, of at least one of the compounds > of the following general formula: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D and E are fluorine atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D and E are fluorine atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) > or the following general formula: in which: • B, C, D and E are fluorine atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for coupling reactions.

12. Use of compounds of formula (I), according to any one of claims 1 to 8, selected from: A is chosen from: a group -X in which X is chosen from o a chlorine atom o a bromine atom a group in which: M is a coordinating solvent; p is chosen from 1, 2, 3, 4, or a decimal number that can vary from a value greater than 0 but less than 4; a group • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • when A corresponds to the grouping then R1, R5, R6, and R 10The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1, 2, or 4 to 10 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atom(s), or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and R2, R3, R4, R7, R8, and R9. are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • when A corresponds to the grouping -X or to the grouping then R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, the compound with the following formula being excluded:

14. Compound, according to claim 12 > of the following general formula (I): in which: • A, , R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and G have the meanings indicated in claim 11 • B, C, D, and E, whether identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and at least one of B, C, D, or E is different from a hydrogen atom > or the following general formula (I): in which: • A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and G have the meanings indicated in claim 11 • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular an alkyl group linear or branched of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and at least one of B, C, D, or E is a halogen, in particular F > or the following general formula (I): in which • A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and G have the meanings indicated in claim 11 • B, C, D, and E are fluorine atoms 15. Compound > of the following general formula: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular an alkyl group linear or branched of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atom(s), or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms > or the following general formula: in which X and G have the meanings indicated above, and • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6. R7, R8, R9and R 10The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9 > or the following general formula: in which X and G have the meanings indicated above, and • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5, R2 is identical to R4, and R6 is identical to R 10 R7 is identical to R9 > or the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D, and E, whether identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R5, R6 and R 10, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3. a linear or branched alkyl group of 1 to 2 or 4 to 10 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 1 to 20 carbon atoms, and R2, R3, R4, R7, R8, and R9, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, the compound with the following formula being excluded: > or the following general formula (Ib): in which X, M, p and G have the meanings indicated above, and • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C R1, R5, R6 and R 10, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 2 or 4 to 10 carbon atom(s), a linear or branched alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and R2, R3, R4, R7, R8, and R9. are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is different from R 10 and / or R7 is different from R9 > or the following general formula (Ib) in which X, M, p and G have the meanings indicated above, and • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R5, R6 and R 10, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 2 or 4 to 10 carbon atom(s), a linear or branched alkoxyl group of 1 to 10 carbon atom(s), or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and R2, R3, R4, R6, R7, and R9. identical, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular a linear or branched alkyl group of 2 to 4 carbon atoms, an alkoxyl group linear or branched of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5, R2 is identical to R4, R6 is identical to R 10 R7 si is identical to R9, the composition of the following formula being excluded:

16. Compound > of the following general formula: in which: • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms > or the following general formula: in which: • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 , identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a group a linear or branched alkoxyl of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is identical to R5, R2 is identical to R4, R6 is identical to R 10 R7 is identical to R9 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms > or the following general formula: in which: • B, C, D, and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4 and R6 is identical to R 10 and R7 is either identical to R9 or R6 is different from R 10 and / or R7 is either different from R9 and R1, or identical to R5 and R2, or identical to R4 • G is selected from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, or a compound of formula (I) according to any one of claims 13 to 16, selected from: Use of one or at least one of the compounds of formulas (la), (Ib) or (le) according to any one of claims 1 to 12, for the synthesis of one of the compounds of the following formula: 61zT in which Y is chosen from: ▪ a hydrogen atom ▪ a linear or branched alkyl group of 1 to 10 carbon atom(s) ▪ a linear or branched alkoxyl group of 1 to 10 carbon atom(s) ▪ a grouping -OPh ▪ an alkylamino or dialkylamino group, substituted by one or two linear alkyl group(s) of 1 to 10 carbon atom(s) ▪ a halogen, in particular a fluorine atom, a chlorine atom or a bromine atom a nitro group NO2 . a trifluoromethyl group CF3 ▪ a group Use of at least one of the compounds of formulas (la), (Ib) or (le) according to any one of claims 1 to 12 for carrying out a Suzuki-Miyaura reaction from a compound (SI) in which W is chosen from: a phenyl group in which Y is chosen from: ▪ a hydrogen atom ▪ a linear or branched alkyl group of 1 to 10 carbon atom(s) ▪ a linear or branched alkoxyl group of 1 to 10 carbon atom(s) ▪ a grouping -OPh ▪ an alkylamino or dialkylamino group, substituted by one or two linear alkyl group(s) of 1 to 10 carbon atom(s) ▪ a halogen, in particular a fluorine atom, a chlorine atom or a bromine atom a nitro group NO2 . a trifluoromethyl group CF3 a 2-thiophenyl group a 3-fiiranyl group a 2-naphthyl group a 6-quinolyl group a group a group a group a group a group a linear or branched alkyl group of 1 to 20 carbon atoms or a cyclic group of 3 to 12 carbon atoms, in particular an octyl group, a group and V is chosen from: a group in which q is equal to 0 or 1. a grouping with a compound of formula (S2): Z-Hal in which Z is selected from: a linear or branched alkyl group of 1 to 20 carbon atoms or a cyclic group of 3 to 12 carbon atoms, in particular an octyl, hexyl, cycloheptyl, cyclopentyl or cyclopropyl group; an 1-adamantyl group of formula a benzyl group of formula a group a group a group a group a group a group a group a group and Hal is chosen from: a chlorine atom, a bromine atom, an iodine atom. Method for preparing a compound of formula (la), according to claim 15 in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) comprising: a) a condensation step of a compound of formula (V) (V) in which B, C, D, and E have the meanings indicated above and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom b) an aromatic nucleophilic substitution step of said compound of formula (III) on a compound of formula (IV): in which R6, R7, R8, R9, and R 10 have the meanings indicated above to obtain the compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above c) a step of sequential addition of n-butyl lithium and then of iron(II) halide FeX2 to said compound of formula (II) to obtain the compound of formula (la). Process for preparing a compound of formula (Ib), according to claim 15 in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular an alkyl group a linear or branched alkoxyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 10 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10 The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) comprising: a) a condensation step of a compound of formula (V) in which B, C, D, and E have the meanings indicated above and F is a fluorine atom in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom b) an aromatic nucleophilic substitution step of said compound of formula (III) on a compound of formula (IV): in which R6, R7, R8, R9, and R 10 have the meanings indicated above to obtain the compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above c) a step of sequential addition of n-butyl lithium then of iron (II) halide FeX2 on said compound of formula (II) to obtain the compound of formula (Ib).

22. A method for preparing a compound of formula (the), according to claim 16 in which: • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R2, R3, R4, R5, R6, R7, R8, R9and R 10The components, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms. • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) comprising: a) a condensation step of a compound of formula (V) in which B, C, D, and E have the meanings indicated above, and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom b) an aromatic nucleophilic substitution step of said compound of formula (III) on a compound of formula (IV): in which R6, R7, R8, R9, and R 10 have the meanings indicated above to obtain the compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 have the meanings indicated above, c) a step of sequential addition of n-butyl lithium and then of iron (III) tris-acetylacetonate to said compound of formula (II) to obtain said compound of formula (lc).

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