New iron-based compounds, their preparation processes and their use as catalysts

Abstract

The present invention relates to iron iminoanilidide complexes, their preparation processes and their use as catalysts in the Suzuki-Miyaura reaction. Figures (no figures)

Description

Title of the invention: New iron-based compounds, their preparation processes and their use as catalysts. Technical field

[0001] The present invention relates to the synthesis of new iron-based compounds, their preparation processes and their use as catalysts. Prior art

[0002] Iron is an inexpensive, abundant, readily available, and relatively non-toxic metal (Angew. Chem. Int. Ed. 2016, 55, 12150) and is increasingly replacing palladium in the chemical industry. Indeed, iron offers numerous advantages from a sustainability perspective. Moreover, iron is one of the few base metals that has been successfully tested as a catalyst in industrial cross-coupling processes on a kilogram scale. Iron [3-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, free from humidity and ambient air, in glovebox-type equipment. (Angew. Chem., Int. Ed. 2020, 59, 5392), which represents a constraint that makes these catalysts difficult to use on an industrial scale.

[0003] Indeed, metal catalysis is a means of accelerating, or even enabling, certain reactions and accessing a large number of compounds at production costs far lower than those of conventional organic synthesis routes, which sometimes require a significant number of steps. Furthermore, the requirements for residual metals in products intended for human use, particularly in pharmaceutical products, currently represent a barrier to the use of metal catalysis in the manufacture of such products.

[0004] 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 various types of cross-coupling, the Suzuki-Miyaura coupling (Angew. Chem., Int. Ed. 2011, 50, 6722), which is a coupling between a halogenated 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. Catal. 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 formation reactions, while other reactions Cross-coupling accounts for less than 5%. Indeed, this type of coupling is primarily limited to couplings between two partners bearing an sp2 (or even sp) hybridized carbon, leading to the formation of planar molecules. The ease with which Pd(II)-alkyl intermediates formed during the coupling reaction can be eliminated prevents its widespread application to coupling partners bearing sp3 hybridized carbons. Very few molecules with more complex three-dimensional geometries are accessible to 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).Furthermore, coupling between two partners bearing an sp3 hybridized carbon represents only 1% of the Suzuki-Miyaura reactions described to date, despite the significant presence of C(sp3)-C(sp3) bonds in natural or biologically active molecules.

[0005] 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 this is advantageous from a sustainability perspective. Although a few examples of iron-based catalysts for Suzuki-Miyaura coupling have been described in the prior art, few have been reported as effective for coupling partners bearing sp3-hybridized carbons. Furthermore, they often rely on the use of activated boronic derivatives (using an organolithium or organomagnesium compound), 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.These are generally halides that are difficult to couple due to their steric hindrance.

[0006] The invention aims to remedy the problem mentioned above and to enable the creation of C(sp3)-C(sp2) and C(sp3)-C(sp3) bonds.

[0007] An object of the present invention relates to novel iron iminoanilidide compounds

[0008] Another object of the invention is the use of iron imino-anilidide complexes to catalyze the formation of carbon-carbon bonds, in particular, the Suzuki-Miyaura reaction.

[0009] The invention also aims to provide a catalyst stable in ambient air allowing the creation of carbon-carbon bonds.

[0010] Another object of the invention is to provide methods for preparing iron iminoanilidide complexes that may be advantageous in the Suzuki-Miyaura reaction

[0011] Another object of the invention is to provide new compounds prepared with iron iminoanilidide complexes Description of the invention.

[0012] The present invention relates to the use of at least one of the compounds of the following general formula (I):

[0013] [Chem.l]

[0014] (I)

[0015] in which: • A is chosen from: • a group -X in which X is chosen from - a chlorine atom - a bromine atom • a group

[0016] [Chem.2]

[0017] 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

[0018] [Chem. 3]

[0019]

[0020]

[0021]

[0022]

[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 • Rb, R2, R3, R4, R5, R6, R7, R8, R9 and Rio, 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. It was unexpectedly found that iron iminoanilidide complexes could catalyze the formation of carbon-carbon bonds. A can represent X, this group X being chosen from a chlorine or bromine atom, X(Li-X)-(M)p and (Acac)2. In case of steric hindrance due to the groups B, C, D, E, Rb R2, R3, R4, R5, R6, R7, R8, R9 and R10, A advantageously represents X. When there is little or no steric hindrance due to the B, C, D, E, Rb R2, R3, R4, R5, R6, R7, R8, R9 and R10 groups, A advantageously represents XX(Li-X)-(M)p. The term "coordinating solvent" refers to any solvent capable of stabilizing the electron deficiency of a metal cation by donating some of its negative charge using a lone pair of electrons. The coordinating solvent is chosen from the group consisting of diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, or 1,4-dioxane; preferably, tetrahydrofuran. The value p can be 1, 2, 3, 4, or a decimal number greater than 0 but in- less than 4, preferably 1.

[0024] When A represents two acetyloacetonate groups, the compounds do not degrade or lose their properties under the action of ambient air.

[0025] The expression "ambient air" refers to the surrounding air naturally present in the atmosphere, and whose composition can vary depending on the location or altitude.

[0026] By "linear", we mean the carbon atoms of the alkyl chain, with the exception of those 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, that the carbon atom at the beginning of the chain has only one carbon-carbon bond with the rest of the chain and that the carbon atom at the end of the chain has only one carbon-carbon bond.

[0027] The term “branched” means that each carbon atom in the alkyl chain can comprise 3 to 4 carbon-carbon bonds.

[0028] By “catalyst” is meant a chemical substance which, directly or after transformation by another chemical substance, enables or makes possible a chemical reaction.

[0029] 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 (la):

[0030] [Chem.4]

[0031] (the)

[0032] in which: • X is chosen from - a chlorine atom - 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 trifluoro- group romethyl 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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)

[0033] as catalysts.

[0034] This structure corresponds to the presence of steric hindrance around the iron atom due to the B, C, D, E, Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio groups

[0035] To facilitate understanding of what follows, we arbitrarily consider 3 axes of symmetry (I), (II) and (III) as represented in the diagram below

[0036] [Chem.5]

[0037] Axis (I) creates a 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 a symmetry between Ri and R5, and between R2 and R4. Axis (III) includes the carbon bearing Rs and the carbon bearing the nitrogen of the same phenyl group, and creates a symmetry between R6 and Rio, and between R7 and R9.

[0038] In a particular embodiment, the invention relates to the use, such as

[0039] defined previously, of at least one of the compounds with the following general formula (Ib): [Chem. 6]

[0040]

[0041] (Ib) in which: X is chosen from - a chlorine atom - 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. Ri, R2, R3, R4, R5, Re, R7, Rs, R9, and Rio, 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 dialkylamino group or branched with 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)

[0042] as catalysts.

[0043] This structure corresponds to the absence of steric hindrance, or to the presence of low steric hindrance around the iron atom due to the B, C groups, D, E, Ri, R2, R3, R4, R5, R6, R7, R8, R9 and R10

[0044] Advantageously, the compound of formula (Ib) has the following formula:

[0045] [Chem.7]

[0046] To facilitate understanding of what follows, we arbitrarily consider 3 axes of symmetry (I), (II) and (III) as represented in the diagram below

[0047] [Chem. 8]

[0048] Axis (I) creates a 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 a symmetry between Ri 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 a symmetry between R6 and Rio, and between R7 and R9.

[0049] 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:

[0050] [Chem.9]

[0051] (the)

[0052] 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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)

[0053] as catalysts.

[0054] To facilitate understanding of what follows, we arbitrarily consider 3 axes of symmetry (I), (II) and (III) as represented in the diagram below

[0055] [Chem. 10]

[0056] Axis (I) creates a symmetry between C and D, and between B and E. Axis (II) includes the The carbon bearing R3 and the carbon bearing the nitrogen of the same phenyl group create a symmetry between Ri 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 a symmetry between R6 and Rio, and between R7 and R9.

[0057] 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 (la):

[0058] [Chem. 11]

[0059] (the)

[0060] in which: • X is chosen from - a chlorine atom - a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in by 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. • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4

[0061] and - R6 is different from Rio 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)

[0062] as catalysts.

[0063] This particular embodiment corresponds to an absence of symmetry with respect to axis (I), axis (II) and axis (III).

[0064] 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 (la):

[0065] [Chem. 12]

[0066] (the)

[0067] in which: • X is chosen from - a chlorine atom - a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in by a 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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 atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: • Ri is different from R5 and / or R2 is different from R4

[0068] and • R6 must be identical to R10 and R7 must be identical to R9

[0069] or • R6 must be different from R10 and / or R7 must be different from R9

[0070] and • Ri 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)

[0071] as catalysts.

[0072] This particular embodiment corresponds to the absence of symmetry with respect to axis (I) and axis (II), and the presence of symmetry with respect to axis (III).

[0073] 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 (la):

[0074] [Chem. 13]

[0075] (the)

[0076] in which: • X is chosen from - a chlorine atom - a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in by a 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 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, DouE being different from the others • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is identical to R5 - R2 is identical to R4 - R6 is identical to R10 - 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)

[0077] as catalysts.

[0078] This particular embodiment corresponds to the absence of symmetry with respect to axis (I). It also corresponds to the presence of symmetry with respect to axis (II) and axis (HD).

[0079] 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 (la):

[0080] [Chem. 14]

[0081] (the)

[0082] in which: • X is chosen from - a chlorine atom - 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4

[0083] and - R6 is different from Rio 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)

[0084] as catalysts.

[0085] This particular embodiment corresponds to the presence of symmetry with respect to axis (I). It also corresponds to the absence of symmetry with respect to axis (II) and axis (III).

[0086] 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 (la):

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] (there) 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 alkoxy 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. Rb, R2, R3, R4, R5, R6, R7, Rs, R9, and Rio 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. branched with 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, provided that: - Ri is different from R5 and / or R2 is different from R4 and R6 is identical to R10 and R7 is identical to R9 or R6 must be different from R10 and / or R7 must be different from R9 and Ri 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)

[0093] as catalysts.

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

[0095] 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 (la): [Chem. 16]

[0097]

[0098] (there) 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9, and Rio 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: - Ri is identical to R5 - R2 is identical to R4 - R6 is identical to R10 - 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)

[0099] as catalysts.

[0100] This particular embodiment corresponds to the presence of symmetry with respect to axis (I), axis (II) and axis (HD

[0101] 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 (la):

[0102] [Chem. 17]

[0103] (the)

[0104] in which: • X is chosen from - a chlorine atom - a bromine atom • B, C, D and E are fluorine atoms • Rb, R2, R4, R5, R6, R7, Rs, R9 and Rio, 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)

[0105] as catalysts.

[0106] This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl group bearing groups B, C, D and E. This has the effect of modifying the electronic properties of the iron atom of the catalyst.

[0107] 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 (Ib):

[0108] [Chem. 18]

[0109] (Ib)

[0110] in which: • X is chosen from - a chlorine atom - 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, DouE being different from the others. • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4 [YES] and - R6 must be different from R10 and / or R7 must be different from R9 • G is chosen from - a hydrogen atom - a linear or branched alkyl group of 1 to 5 carbon atom(s)

[0112] as catalysts.

[0113] This particular embodiment corresponds to an absence of symmetry with respect to axis (I), axis (II) and axis (III).

[0114] 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 (Ib):

[0115] [Chem. 19]

[0116] (Ib)

[0117] in which: • X is chosen from - a chlorine atom - 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, with at least one of the groups B, C, D, or E being different from the others • Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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: • Ri is different from R5 and / or R2 is different from R4

[0118] and • R6 is identical to R10 and R7 is identical to R9

[0119] or • R6 is different from R10 and / or R7 is different from R9

[0120] and • Ri 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)

[0121] as catalysts.

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

[0123] 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 (Ib):

[0124] [Chem. 20]

[0125]

[0126] (Ib) in which: X is chosen from a chlorine atom, 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. Rb, R2, R3, R4, R5, R6, R7, Rs, R9, and Rio 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 group 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, provided that: Ri is identical to R5 R2 is identical to R4 R6 is identical to R10 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)

[0127] as catalysts.

[0128] This particular embodiment corresponds to the absence of symmetry with respect to axis (I). It also corresponds to the presence of symmetry with respect to axis (II) and axis (HD).

[0129] 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 (Ib):

[0130] [Chem.21]

[0131]

[0132] (Ib) in which: X is chosen from a chlorine atom 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, an alkyl group linear or branched 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4

[0133] and - R6 is different from Rio 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)

[0134] as catalysts.

[0135] This particular embodiment corresponds to the presence of symmetry with respect to axis (I). It also corresponds to the absence of symmetry with respect to axis (II) and axis (III).

[0136] 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 (Ib):

[0137] [Chem.22]

[0138] (Ib)

[0139] in which: • X is chosen from - a chlorine atom - 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 • Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4

[0140] and - R6 is identical to R10 and R7 is identical to R9

[0141] or - R6 must be different from R10 and / or R7 must be different from R9

[0142] and - Ri 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)

[0143] as catalysts.

[0144] This particular embodiment corresponds to the presence of symmetry with respect to axis (I) and axis (III). It also corresponds to the absence of symmetry with respect to axis (II).

[0145] 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 (Ib):

[0146] [Chem.23]

[0147] (Ib)

[0148] in which: • X is chosen from - a chlorine atom - 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is identical to R5 - R2 is identical to R4 - R6 is identical to Rio - 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)

[0149] as catalysts.

[0150] This particular embodiment corresponds to the presence of symmetry with respect to axis (I), axis (II) and axis (HD

[0151] 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 (Ib):

[0152] [Chem.24]

[0153] (Ib)

[0154] in which: • X is chosen from - a chlorine atom - 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, identical or different, are chosen among: 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)

[0155] as catalysts.

[0156] This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl group bearing groups B, C, D and E. This has the effect of modifying the electronic properties of the iron atom of the catalyst.

[0157] 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:

[0159] (the)

[0160] 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4

[0161] and R6 is different from Rio 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)

[0162] as catalysts.

[0163] This particular embodiment corresponds to an absence of symmetry with respect to axis (I), axis (II) and axis (III).

[0164] 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:

[0165] [Chem.26]

[0166] (the)

[0167] 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] And - R6 is identical to Ri0 and R7 is identical to R9 or - R6 must be different from R10 and / or R7 must be different from R9 and - Ri 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) as catalysts. This particular embodiment corresponds to the absence of symmetry with respect to axis (I) and axis (II), and the presence of symmetry with respect to axis (III). 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: (THE) 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 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, DouE being different from the others • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is identical to R5 - R2 is identical to R4 - R6 is identical to R10 - 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)

[0177] as catalysts.

[0178] This particular embodiment corresponds to the absence of symmetry with respect to axis (I). It also corresponds to the presence of symmetry with respect to axis (II) and axis (HD).

[0179] 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:

[0180] [Chem.28]

[0181] (the)

[0182] 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4

[0183] and - R6 is different from Rio 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)

[0184] as catalysts.

[0185] This particular embodiment corresponds to the presence of symmetry with respect to axis (I). It also corresponds to the absence of symmetry with respect to axis (II) and axis (III).

[0186] 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:

[0188] (the)

[0189] 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4

[0190] and - R6 is identical to Rio and R7 is identical to R9

[0191] or - R6 must be different from R10 and / or R7 must be different from R9

[0192] and Ri 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)

[0193] as catalysts.

[0194] This particular embodiment corresponds to the presence of symmetry with respect to axis (I) and axis (III). It also corresponds to the absence of symmetry with respect to axis (II).

[0195] 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:

[0196] [Chem.30]

[0197] (the)

[0198] 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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 atom(s), or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: - Ri is identical to R5 - R2 is identical to R4 - R6 is identical to R10 - 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)

[0199] as catalysts.

[0200] This particular embodiment corresponds to the presence of symmetry by in relation to axis (I), axis (II) and axis (HD

[0201] 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:

[0202] [Chem.31]

[0203] (the)

[0204] in which: • B, C, D and E are fluorine atoms • Rb, R2, R4, R5, R6, R7, Rs, R9 and Rio, identical or different, are chosen among: 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 alkyl group 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 • G is chosen from - a hydrogen atom - a linear or branched alkyl group of 1 to 5 carbon atom(s)

[0205] as catalysts.

[0206] This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl group bearing groups B, C, D and E. This has the effect of modifying the electronic properties of the iron atom of the catalyst

[0207] In another embodiment, the invention relates, as defined above, to the use of compounds of formula (I), selected from:

[0208] [Chem.32]

[0209] The invention relates in particular to the compound, with the following general formula (I):

[0210]

[0211] (I)

[0212] A is chosen from: - a grouping -X in which X is chosen from - a chlorine atom - a bromine atom - a group

[0213] [Chem.34]

[0214] 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

[0215] [Chem.35] 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 a linear or branched alkyl group of 2 to 4

[0216] 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, DouE being other than a hydrogen atom • when A corresponds to the grouping [Chem.36]

[0217]

[0218] then Rb, R5, R6, and Rio, 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 Rç), 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 atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms • when A corresponds to the group -X or to the group [Chem.37]

[0219] Then Rb, R2, R3, R4, R5, R6, R7, R8, R9, and Rio, 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

[0220]

[0221]

[0222] In this particular embodiment, at least one of the groups B, C, D and E is different from a hydrogen atom, and there may be presence or absence of symmetry with respect to axis (I), axis (II) or axis (III). The invention relates in particular to the compound, with the following general formula (I):

[0223]

[0224] A is chosen from: a group -X in which X is chosen from a chlorine atom a bromine atom

[0225] - a grouping [Chem. 39]

[0226] 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

[0227] [Chem.40] 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. Rb, R5, R6, and Rio, 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 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. R2, R3, R4, Re, R7, Rs, 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

[0228] The compound with the following formula is excluded:

[0229] [Chem.41]

[0230] In this particular embodiment, there may be presence or absence of symmetry with respect to axis (I), axis (II) or axis (III).

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

[0232] [Chem.42]

[0233] (I)

[0234] in which: • A, X, M, p, Rb, R2, R3, R4, R5, R6, R7, R8, R9, Rio and G have the meanings indicated above • 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 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 and at least one of B, C, D or E is different from a hydrogen atom.

[0235] In this particular embodiment, at least one of the groups B, C, D and E is different from a hydrogen atom, and there may be presence or absence of symmetry with respect to axis (I), axis (II) or axis (III).

[0236] The invention relates in particular to the compound as defined above, of the following general formula (I): [Chem. 43]

[0238]

[0239] (I) in which: A, X, M, p, Rb, R2, R3, R4, R5, R6, R7, Rs, R9, Rio and G have the meanings indicated above 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 a halogen, in particular F

[0240] In this particular embodiment, at least one of the groups B, C, D and E is a fluorine atom, and there may be presence or absence of symmetry with respect to axis (I), axis (II) or axis (III).

[0241] The invention relates in particular to the compound as defined above, of the following general formula (I):

[0242]

[0243] (I)

[0244] in which • A, X, M, p, Rb, R2, R3, R4, R5, R6, R7, R8, R9, Rio and G have the meanings indicated above • B, C, D, and E are fluorine atoms

[0245] In this particular embodiment, groups B, C, D, and E are fluorine atoms. This results in a modification of the electronic properties of the iron atom of the catalyst, and there is symmetry with respect to axis (I). There may or may not be symmetry with respect to axis (II) or axis (HD).

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

[0248] (the)

[0249] in which: • X is chosen from - a chlorine atom - a bromine atom • B, C, D, and E, identical or different, are chosen from: an atom hydrogen, 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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

[0250] The invention relates in particular to the compound as defined above, of the following general formula:

[0251] [Chem.46]

[0252] (the)

[0253] wherein X and G have the meanings given in claim 32, 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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: - Ri is different from R5 and / or R2 is different from R4

[0254] and - R6 must be different from R10 and / or R7 must be different from R9

[0255] In this particular embodiment, there is a symmetry with respect to axis (I) and an absence of symmetry with respect to axis (II) and axis (III).

[0256] The invention relates in particular to the compound as defined above, of the following general formula (la):

[0257] [Chem.47]

[0258] (the)

[0259] 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9, and Rio, 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 alkyl group 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, provided that: Ri is identical to R5 R2 is identical to R4 R6 is identical to R10 R7 is identical to R9

[0260] In this particular embodiment, there is a symmetry with respect to axis (I), axis (II) and axis (III)

[0261] The invention relates in particular to the compound as defined above, of

[0262] The following general formula (Ib): [Chem.48]

[0263]

[0264] (Ib) in which X is chosen from a chlorine atom 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 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 • Rb R5, R6 and Rio, 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 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 1 to 20 carbon atom(s), 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 atom(s), in particular a linear or branched alkyl group of 2 to 4 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 • G is chosen from - a hydrogen atom - a linear or branched alkyl group of 1 to 5 carbon atoms

[0265] the compound of the following formula being excluded:

[0266] [Chem.49]

[0267] The invention relates in particular to the compound as defined above, of the following general formula (Ib):

[0268] [Chem. 50]

[0269]

[0270] in which X, M, p and G have the meanings given in claim 35, and B, C, D and E are selected 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, provided that B is identical to E and that D is identical to C. Ri, R5, R6 and Rio are selected 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, R7, Rs, and Rç),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, provided that: , Ri must be different from R5 and / or R2 must be different from R4

[0271] and - R6 must be different from Ri0 and / or R7 must be different from R9

[0272] In this particular embodiment, there is symmetry with respect to axis (I) and no symmetry with respect to axis (II) and axis (HD)

[0273] The invention relates in particular to the compound as defined above, of the following general formula (Ib):

[0274] [Chem.51]

[0275] (Ib)

[0276] wherein X, M, p and G have the meanings given in claim 35, 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 • Ri, R5, R6 and Rio 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 trifluoro- romethyl 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, provided that: Ri is identical to R5 R2 is identical to R4 R6 is identical to R10 R7 is identical to R9

[0277]

[0278] the compound of the following formula being excluded: [Chem. 52]

[0279] In this particular embodiment, there is a symmetry with respect to axis (I), axis (II) and axis (III).

[0280] The invention relates in particular to the compound, of the following general formula:

[0282] (the)

[0283] 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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

[0284] The invention relates in particular to the compound as defined above, of the following general formula:

[0286] (the)

[0287] in which: • 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 D is identical to C • Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio, 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: - Ri is identical to R5 - R2 is identical to R4 - R6 is identical to R10 - R7 is identical to R9 • G is chosen from - a hydrogen atom - a linear or branched alkyl group of 1 to 5 carbon atoms

[0288] In this particular embodiment, there is a symmetry with respect to axis (I), axis (II) and axis (III).

[0289] The invention relates in particular to the compound as defined above, of the following general formula:

[0290] [Chem.55]

[0291] (the)

[0292] in which: • 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 D is identical to C • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4

[0293] and - R6 is identical to Ri0 and R7 is identical to R9

[0294] or - R6 must be different from R10 and / or R7 must be different from R9

[0295] and - Ri 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 atoms

[0296] In this particular embodiment, there is symmetry with respect to axis (I). There is also an absence of symmetry with respect to axis (II) and axis (HD

[0297] The invention relates in particular to the compound as defined above, selected from:

[0298] [Chem.56]

[0299] In a particular embodiment, the present invention relates to the use of at least one of the compounds of formulas (la), (Ib) or (le) as defined above as a catalyst for carrying out a reaction, chosen from among carbon-carbon bond-forming reactions such as the Suzuki-Miyaura, Kumada and Sonogashira reactions,

[0300] The expression "carbon-carbon bond formation reaction" means that in the overall reaction, a carbon-carbon bond will have been created between two distinct molecules or in an intramolecular manner.

[0301] In another embodiment, the compound of formula (la), (Ib) or (le) is used, as defined above, at catalytic charges of 0.01 mol% to 0.1 mol%, from 0.1 mol% to 1 mol%, from 1 mol% to 10 mol%, from 10 mol% at 20% molar and from 20% molar to 30% molar, preferably from 1% molar to 10% molar.

[0302] The term “catalytic charge” refers to the percentage molar equivalent at which the catalyst is introduced.

[0303] In another embodiment, the invention relates to the use of the compounds, as defined above, in order to carry out the Suzuki-Miyaura reaction

[0304] By way of 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 under stirring at 25°C for 24h.

[0305] The use of these compounds in a Suzuki-Miyaura reaction can be done in benzene, toluene, 2-methyltetrahydrofuran, methyl tert-butyl ether and anisole, preferably in benzene.

[0306] These catalysts can be activated during a Suzuki-Miyaura reaction by thermal heating, by microwave, preferably by thermal heating.

[0307] The reaction medium can be heated to temperatures from 25°C to 150°C, preferably at 25°C.

[0308] The use of these catalysts in a Suzuki-Miyaura reaction can be done in batch or continuous flow, preferably in batch.

[0309] In another embodiment, the invention relates to the use of the compounds, as defined above, in which the implementation of the Suzuki-Miyaura reaction includes the use of a base selected from LiNMeEt, LiNMe2, LiNEt2, LiNiPr2, LiNTMS2, LiNPhMe, in particular LiNMeEt and LiNMe2.

[0310] In another embodiment, the use as defined above, for the synthesis of compounds of the following formula:

[0311] [Chem.57] CXPh Hj€ Ph —' / Ph s

[0312] [Chem.58]

[0314] 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 group -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 an atom

[0315]

[0316] bromine a nitro group NO2 a trifluoromethyl group CF3 The invention relates in particular to compounds of the following formula [Chem. 60] Boc

[0317]

[0318]

[0319]

[0320]

[0321]

[0322] In another embodiment, the invention relates to the use as defined above of a compound of formula (la), (Ib) or (le) for carrying out a Suzuki-Miyaura reaction from a compound of formula (SI) [Chem.61] B — V W (If) in which W is chosen from: - a phenyl group [Chem. 62] 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 atoms, a -OPh group 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

[0323] [Chem.63] a 2-furanyl group

[0324] [Chem.64] - a 2-naphtyl group

[0325] [Chem.65] - a 6-quinolyl group

[0326] [Chem.66] - a group

[0327] [Chem.67] - a group

[0328] [Chem.68] a group

[0329] [Chem. 69] a group

[0330] [Chem.70] - 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

[0331] and V is chosen from: - a group

[0332] [Chem.71] in which q is equal to 0 or 1. - a grouping

[0333] [Chem.72]

[0334] with a compound of formula (S2): Z-Hal

[0335] in which Z is chosen 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 or cycloheptyl group - an 1-adamantyl group with the formula

[0336] [Chem.73]

[0337] - a benzyl group of formula [Chem. 74]

[0338] - a group [Chem.75]

[0339]

[0340] - a group [Chem.76] - a group [Chem.77] - a group

[0341] [Chem.78]

[0342] a group

[0343] [Chem. 80]

[0344] and Hal is chosen from: - a chlorine atom - a bromine atom - an iodine atom

[0345] In one embodiment, the present invention relates to a method for preparing a compound of formula (la) as defined above: [Chem.81]

[0347]

[0348] (there) 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. Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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)

[0349] comprising a step of sequential addition of n-butyl-lithium and then of iron (II) halide FeX2 to a compound of formula (II) [Chem. 82]

[0351] (II)

[0352] in which B, C, D, E, G, Rb R2, R3, R4, R5, R6, R7, Rs, R9 and R10 have the meanings indicated above.

[0353] In this embodiment, the addition reaction consists of the deprotonation of the secondary amine function of compound (II) located between two phenyl groups to create the N-Fe bond. Lithium does not coordinate to compound (la) due to steric hindrance around the iron atom caused by groups B, C, D, E, R1, R2, R2, R4, R5, R6, R7, Rs, R9, and Rio. The resulting compound (la) is sensitive to oxygen and must be stored under inert atmospheric conditions.

[0354] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned addition step is carried out in a cyclic or non-cyclic ether solvent, in particular selected from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane or methoxycyclopentane, 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.

[0355] The expression "etheric solvent" designates a solvent in which there is at least one ether function.

[0356] 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.

[0357] By way of 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 to hexane, then for the addition of FeX2 to a cyclic or non-cyclic ether solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, the tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane or methoxycyclopentane.

[0358] By way of 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 nonpolar solvent in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, and then for the addition of FeX2 in tetrahydrofuran.

[0359] By "non-coordinating nonpolar solvent" is meant a solvent in which the center of gravity of the sums of the differences in electronegativity coincide,

[0360] By way of non-limiting example, this step of adding n-butyllithium and Fe2 chloride (1 / 1) can be carried out in tetrahydrofuran at temperatures from -78°C to 25°C, preferably -78°C to -30°C for 30 minutes, then 2h from -78°C to 25°C, preferably from 0°C to 25°C, then 15h from -78°C to 25°C, preferably from 0°C to 25°C under stirring.

[0361] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (II):

[0363] (II)

[0364] in which B, C, D, E, G, Rb R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the meanings indicated above, said step, comprising an aromatic nucleophilic substitution step of a compound of formula (III)

[0365] [Chem. 84]

[0367] wherein B, C, D, E, G, Rb, R2, R2, R4, and R5 have the meanings indicated above, and F is a fluorine atom

[0368] on a compound of formula (IV):

[0369] [Chem. 85]

[0370] (IV)

[0371] in which R6, R7, R8, R9, and R10 have the meanings indicated above

[0372] to obtain said compound of formula (II)

[0373] compounds of the following formula being excluded:

[0374] [Chem. 86]

[0375] In this embodiment, the aromatic nucleophilic substitution occurs via the lithium amide of compound (IV) which substitutes for the fluorine of compound (III).

[0376] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned aromatic nucleophilic substitution step is carried out in a cyclic or non-cyclic ether solvent, in particular selected from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane or methoxycyclopentane, preferably tetrahydrofuran and at a temperature of 25°C to 125°C, preferably at 25°C.

[0377] By way of non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at temperatures from 25 °C to 125 °C, preferably from 25 °C to 75 °C.

[0378] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned aromatic nucleophilic substitution step is carried out in a non-coordinating nonpolar solvent, in particular selected 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.

[0379] By way of non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2,5 / 1) is carried out in toluene at temperatures from 25°C to 125°C, preferably from 25°C to 75°C.

[0380] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (III)

[0381] [Chem.87]

[0382] (III)

[0383] wherein B, C, D, E, G, Rb, R2, R3, R4, and R5 have the meanings given in claim 51, and F is a fluorine atom

[0384] said step comprising a condensation reaction of a compound of formula (V)

[0385] [Chem.88] FO U

[0386] (V)

[0387] in which B, C, D, and E have the meanings indicated above, and F is a fluorine atom

[0388] on a compound of formula (VI):

[0389] [Chem.89] R"

[0390] (VI)

[0391] in which Rb R2, R3, R4, and R5 have the meanings indicated above

[0392] to obtain said compound of formula (III)

[0393] compounds of the following formula being excluded:

[0394] [Chem.90]

[0395] In this embodiment, the condensation step forming compound (III) is carried out from an aldehyde, compound (V) and an amine, compound (IV).

[0396] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned condensation step is carried out, at a temperature from 0°C to 150°C, in a non-coordinating or alcoholic nonpolar solvent, in particular selected 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.

[0397] The expression "alcoholic solvent" refers to a solvent which contains a hydroxyl function.

[0398] By way of 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 from 25°C to 75°C, preferably at 25°C.

[0399] By way of 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 from 25°C to 150°C, preferably at 150°C.

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

[0401] In another embodiment, the present invention relates to a method of pre preparation, as defined above, of a compound of formula (la)

[0402] [Chem.91]

[0403]

[0404] (there) 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. • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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)

[0405] comprising: a) a condensation step of a compound of formula (V)

[0406] [Chem.92]

[0407] (V)

[0408] in which B, C, D, and E have the meanings indicated above and F is a fluorine atom

[0409] on a compound of formula (VI):

[0410] [Chem.93]

[0411] (VI)

[0412] in which Rb R2, R3, R4, and R5 have the meanings indicated above

[0413] to obtain the compound of formula (III)

[0414] [Chem.94]

[0415] (III)

[0416] wherein B, C, D, E, G, Rb, R2, R2, R4, and R5 have the meanings indicated above, and F is a fluorine atony

[0417] b) an aromatic nucleophilic substitution step of said compound of formula (III) on a compound of formula (IV):

[0418] [Chem.95]

[0419] (IV)

[0420] in which R6, R7, R8, R9, and R10 have the meanings indicated above

[0421] to obtain the compound of formula (II)

[0423] (II)

[0424] in which B, C, D, E, G, Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and R10 have the meanings indicated above

[0425] 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).

[0426] In another embodiment, the present invention relates to a method for preparing, as defined above, a compound of formula (Ib):

[0427] [Chem.97]

[0428]

[0429] (Ib) in which: X is chosen from a chlorine atom 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 75 20 carbon atoms • Rb R2, R3, R4, R5, R6, R7, R8, R9 and Rio, 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)

[0430] comprising a sequential addition step of n-butyllithium followed by halide of iron (II) FeX2 on a compound of formula (II)

[0431] [Chem.98]

[0433] in which B, C, D, E, G, Rb R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the meanings indicated above.

[0434] In this embodiment, the addition reaction 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 bonded to iron coordinates to a lithium atom, itself already coordinated by another X atom. This coordination can occur in the absence or presence of slight steric hindrance around the iron atom due to the B, C, D, E, Rb, R2, R3, R4, R5, R6, R7, R8, R9, and Rio groups. The resulting compound is sensitive to ambient air and must be stored under inert atmospheric conditions.

[0435] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned 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-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane or methoxycyclopentane, preferably tetrahydrofuran, from -78°C to 25°C, preferably at -78°C, for 30 minutes, then 2h at 25°C, then 15h at 25°C with stirring.

[0436] 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.

[0437] By way of 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 into hexane, then for the addition of FeX2 into a cyclic or non-cyclic ether solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane or methoxycyclopentane.

[0438] By way of 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 nonpolar solvent in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, and then for the addition of FeX2 in tetrahydrofuran.

[0439] By way of non-limiting example, this step of adding n-butyllithium and FeCl2 (1 / 1) can be carried out in tetrahydrofuran at temperatures of -78°C to 25°C, preferably -78°C to -30°C for 30 minutes, then 2h from -78°C to 25°C, preferably from 0°C to 25°C, then 15h from -78°C to 25°C, preferably from 0°C to 25°C under stirring.

[0440] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (II):

[0441] [Chem.99]

[0442] (II)

[0443] wherein B, C, D, E, G, Rb R2, R3, R4, R5, R6, R7, Rs, R9 and R10 have the meanings given in claim 57, said step, comprising an aromatic nucleophilic substitution step of a compound of formula (III)

[0444] [Chem. 100]

[0445]

[0446] in which B, C, D, E, G, Rb, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom

[0447] on a compound of formula (IV):

[0448] [Chem. 101]

[0449] (IV)

[0450] in which R6, R7, R8, R9, and R10 have the meanings indicated above

[0451] to obtain said compound of formula (II)

[0452] compounds of the following formula being excluded:

[0453] [Chem. 102]

[0455] In this embodiment, the aromatic nucleophilic substitution occurs via the lithium amide of compound (IV) which substitutes for the fluorine of compound (III).

[0456] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned aromatic nucleophilic substitution step is carried out in a cyclic or non-cyclic ether solvent, in particular selected from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane or methoxycyclopentane, preferably tetrahydrofuran and at a temperature of 25°C to 125°C, preferably at 25°C.

[0457] By way of non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at temperatures from 25 °C to 125 °C, preferably from 25 °C to 75 °C.

[0458] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned aromatic nucleophilic substitution step is carried out in a non-coordinating nonpolar solvent, in particular selected 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.

[0459] By way of non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2,5 / 1) is carried out in toluene at temperatures from 25°C to 125°C, preferably from 25°C to 75°C.

[0460] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (III)

[0461] [Chem. 104]

[0462] (III)

[0463] wherein B, C, D, E, G, Rb, R2, R3, R4, and R5 have the meanings indicated above previously, and F is a fluorine atom

[0464] said step comprising a condensation reaction of a compound of formula (V)

[0465] [Chem. 105]

[0466] (V)

[0467] in which B, C, D, and E have the meanings indicated above, and F is a fluorine atom

[0468] on a compound of formula (VI):

[0469] [Chem. 106]

[0470] (VI)

[0471] in which Rb R2, R3, R4, and R5 have the meanings indicated above

[0472] to obtain said compound of formula (III)

[0473] compounds of the following formula being excluded:

[0475] 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).

[0476] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned condensation step is carried out, at a temperature of 0°C to 150°C, in a non-coordinating nonpolar or alcoholic solvent, in particular selected 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.

[0477] By way of 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 from 25°C to 75°C, preferably at 25°C.

[0478] By way of 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 from 25°C to 150°C, preferably at 150°C

[0479] By way of non-limiting example, this condensation of an aldehyde and an amine (1 / 1,1) takes place in ethanol at temperatures from 25°C to 90°C, preferably at 25°C

[0480] In another embodiment, the present invention relates to a method for preparing, as defined above, a compound of formula (Ib)

[0481] [Chem. 108]

[0482] (Ib)

[0483] in which: • X is chosen from - a chlorine atom - 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 10 carbon atoms • Rb, R2, R3, R4, R5, R6, R7, Rs, R9, and Rio, 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 dialkylamino group or branched with 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)

[0484] comprising: a) a condensation step of a compound of formula (V)

[0485] [Chem. 109] IJ

[0486] (V)

[0487] in which B, C, D, and E have the meanings indicated above and F is a fluorine atom

[0488] on a compound of formula (VI):

[0489] [Chem. 110]

[0490] (VI)

[0491] in which Rb R2, R3, R4, and R5 have the meanings indicated above

[0492] to obtain the compound of formula (III)

[0493] [Chem. 111]

[0494] (III)

[0495] in which B, C, D, E, G, Rb, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom

[0496] b) an aromatic nucleophilic substitution step of said compound of formula (III) on a compound of formula (IV):

[0497] [Chem. 112]

[0498] (IV)

[0499] in which R6, R7, R8, R9, and Rio have the meanings indicated above

[0500] to obtain the compound of formula (II)

[0501]

[0502]

[0503] in which B, C, D, E, G, Rb, R2, R3, R4, R5, Re, R7, R8, R9 and Rio have the meanings indicated above

[0504] 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 (Ib).

[0505] In a particular embodiment, the present invention relates to a method for preparing, as defined above, a compound of formula (the):

[0507]

[0508]

[0506] (THE) 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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 sequential addition step of n-butyl lithium, then of iron (III) tris-acetylacetonate on a compound of formula (II)

[0511] (II)

[0512] in which B, C, D, E, G, Rb, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio have the meanings indicated above

[0513] to obtain said compound of formula (the).

[0514] In this embodiment, the addition reaction here consists of the deprotonation of The secondary amine function of compound (II) is positioned between two phenyl groups to create the N-Fe bond. The compounds of formula (le) thus obtained are stable in ambient air.

[0515] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned addition step is carried out in a cyclic or non-cyclic ether solvent, in particular selected from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane or methoxycyclopentane, preferably tetrahydrofuran, from -78°C to 25°C, preferably at 25°C, then for 16 hours at 25°C with stirring.

[0516] 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.

[0517] By way of non-limiting example, this sequential addition step 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 ether solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane or methoxycyclopentane.

[0518] By way of 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 nonpolar solvent in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, and then for the addition of Fe(acac)3 in tetrahydrofuran.

[0519] By way of non-limiting example, this step of adding n-butyllithium and Fe(acac)3 (1 / 1) can be carried out in tetrahydrofuran at temperatures from -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.

[0520] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (II):

[0521] [Chem. 116]

[0523] in which B, C, D, E, G, Rb R2, R3, R4, R5, R6, R7, Rs, R9 and R10 have the meanings indicated above, said step, comprising an aromatic nucleophilic substitution step of a compound of formula (III)

[0524] [Chem. 117]

[0525] (III)

[0526] wherein B, C, D, E, G, Rb, R2, R2, R4, and R5 have the meanings indicated above, and F is a fluorine atom

[0527] on a compound of formula (IV):

[0528] [Chem. 118]

[0529] (IV)

[0530] in which R6, R7, R8, R9, and Rio have the meanings indicated above

[0531] to obtain said compound of formula (II).

[0532] In this embodiment, the aromatic nucleophilic substitution occurs via the lithium amide of compound (IV) which substitutes for the fluorine of compound (III).

[0533] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned aromatic substitution step is carried out in a cyclic or non-cyclic ether solvent, in particular chosen from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane or methoxycyclopentane, preferably tetrahydrofuran and at a temperature of 25°C to 125°C, preferably at 25°C.

[0534] By way of non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) takes place in tetrahydrofuran at temp- temperatures from 25°C to 125°C, preferably from 25°C to 75°C.

[0535] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned addition step is carried out in a non-coordinating nonpolar solvent, in particular selected 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.

[0536] By way of non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures from 25°C to 125°C, preferably from 90°C to 125°C. By way of non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures from 25°C to 125°C, preferably from 25°C to 75°C.

[0537] In another embodiment, the present invention relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (III)

[0539] (III)

[0540] in which B, C, D, E, G, Rb, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom

[0541] said step, comprising a condensation step of a compound of formula (V)

[0542] [Chem. 120]

[0544] wherein B, C, D, E, G, Rb, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atony

[0545] on a compound of formula (VI):

[0546] [Chem. 121]

[0547] (VI)

[0548] in which Rb R2, R3, R4, and R5 have the meanings indicated above, to obtain said compound of formula (III).

[0549] In this embodiment, the imine formation step of compound (III) is carried out from an aldehyde, compound (V) and an amine, compound (IV).

[0550] In another embodiment, the present invention relates to a preparation process, as defined above, in which the aforementioned condensation step is carried out, at a temperature of 0°C to 150°C, in a non-coordinating nonpolar or alcoholic solvent, in particular selected 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.

[0551] By way of 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 from 25°C to 75°C, preferably at 25°C.

[0552] By way of 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 from 25°C to 150°C, preferably at 150°C

[0553] By way of non-limiting example, this condensation of an aldehyde and an amine (1 / 1,1) takes place in ethanol at temperatures from 25°C to 90°C, preferably at 25°C

[0554] In another embodiment, the present invention relates to a method for preparing, as defined above, a compound of formula (the)

[0556]

[0557]

[0555] (THE) 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. Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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)

[0559] [Chem. 123]

[0560] (V)

[0561] wherein B, C, D, and E have the meanings indicated above, and F is a fluorine atom

[0562] on a compound of formula (VI):

[0563] [Chem. 124]

[0564] (VI)

[0565] in which Rb R2, R3, R4, and R5 have the meanings indicated above

[0566] to obtain the compound of formula (III)

[0567] [Chem. 125]

[0568] (III)

[0569] wherein B, C, D, E, G, Rb, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom

[0570] b) an aromatic nucleophilic substitution step of said compound of formula (III) on a compound of formula (IV):

[0571] [Chem. 126]

[0572]

[0573] in which R6, R7, R8, R9, and R10 have the meanings indicated above

[0574] to obtain the compound of formula (II)

[0575] [Chem. 127]

[0576] (II)

[0577] in which B, C, D, E, G, Rb R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the meanings indicated above,

[0578] 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 (le). Examples Materials and methods

[0579] The ¹³C and ¹³H NMR spectra were acquired at 298 K on a Bruker AM250, AV300, or AV360 MHz spectrometer. The ¹⁷Li and ¹⁹F NMR spectra were acquired at 295 K on a Bruker 300 and 250 spectrometer, respectively. The chemical shifts of the ¹³H spectra were measured using an internal reference of residual protonated CHC13 in CDC13 (7.24 ppm) or residual protonated benzene in benzene-d6 (7.16 ppm).

[0580] Elemental analyses were carried out at Analytische Laboratorien GMBH in Lindlar, Germany.

[0581] High-resolution mass spectra were measured by electron ionization trospray (ESI) with a Bruker MicroTOFq time-of-flight mass spectrometer or a Waters LCT spectrometer using electrospray ionization-time-of-flight mass spectrometry (ESI-TOF)

[0582] The general procedures for the preparation of the compounds are presented below. formulas (la), (II) and (III).

[0583] [Chem. 128]

[0584] (la) (II) (III)

[0585] wherein the groups R2, R4, R7 and R9 represent a hydrogen atom, and the Rh groups R3, R5, R6, R8 and R10 have the meanings set forth in the following table [Table BCDEGXR\R5 R6 R» Rs R3 Rdt (III) Rdt Rdt [%] HHHHH a iiiis Me Me Me 31^ H .....H..... .....H..... HH .....a iPï .....Me....... Me..... H 66^ 57 HH iiiii HR a î?r iiiii R 3&75 J*S H' ""h....... ci îPr iPr HH 76 87 HH ilill HR a ■■■ i?x IIIIII H 31M iiiii HH ■HH Me a iPr iPr HH - 26^ 2S HH OMe HH Ci 11^ rPr ■ ■ i 74 ii FF" F....... ......Ci iPï iPr "'1...... R 66 [a] Procedure Al. [b] Procedure A2. [g] Procedure A3, [d] Procedure Bl. [e] Phx :édure B2.90 ®Ç. [f] Procedure B2.25 '3C. [g] Procedure B3. [h] Procedure Cl. 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 hexane (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) as yellow crystals.

[0586] Procedure A2: In a Dean-Stark apparatus, para-toluenesulfonic acid (0.01 eq) is added with stirring to a solution of the 2-fluorobenzaldehyde derivative Appropriate (1 eq) and appropriate aniline derivative (1.1 eq) in toluene (c = 0.40 M). The solution is heated to 150°C for 15 h. Then, the solution is cooled to 25°C before the addition of a 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 in hexane at -20°C gives the corresponding compound (III) as yellow crystals.

[0587] Procedure A3: 2,6-Diisopropylamine (1.1 eq) is added to a solution of per-fluorobenzaldehyde (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 as yellow crystals.

[0588] Procedure B1: 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 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-colored oil. Recrystallization in hot ethanol or at -20 °C gives the corresponding compound (II) as yellow-colored crystals.

[0589] 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 to 90 °C with stirring for 72 h or to 25 °C for 48 h. The solution is then 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 in hot EtOH gives the corresponding compound (II) as pale yellow crystals.

[0590] Procedure B3: TiCl4 (0.5 eq) was added to a solution of 2,6-diisopropylaniline (3 eq) in hexane (c = 1 M) under stirring at 0 °C. The solution was stirred at 25 °C for 24 h. Then the solution was heated under reflux and a solution of 2-fluoroacetophenone (1 eq) in hexane (c = 2.6 M) was added. The solution was heated under 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 collected and washed with water. The aqueous phase was separated and then extracted with hexane. The organic phases were collected and dried with MgSO4. The mixtures were filtered and concentrated under vacuum 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 was stirred for 18 h and then cannulated into the previously synthesized yellow oil solution in THF at 25 °C. The solution was stirred for 2 h at 25 °C. Water was then added. The aqueous phase was separated and extracted with Et2O. The organic phases were combined, dried with MgSO4, filtered, and the solvent was evaporated under vacuum to obtain a slightly brown oil. The slightly brown oil was recrystallized from hot ethanol to obtain the corresponding compound (II) as a pale white powder.

[0591] 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 minutes 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 (la).

[0592] EXAMPLE 1: Synthesis of (E)-Ά-mesityl-l-(perfluorophenyl)methanimine

[0593] [Chem. 129] F

[0594] 2,4,6-Trimethylaniline (2.3 mL, 16.05 mmol) is added to a solution of per-fluorobenzaldehyde (1.8 mL, 15 mmol) in EtOH (10 mL) at 25 °C and the solution is refluxed (90 °C) for 16 h. After evaporation of the solvent and recrystallization in Et2O at -20 °C, (E)-A-mesityl-l-(perfluorophenyl)methanimine (4.4 g, 14 mmol, 94%) is obtained as yellow crystals. NMR (360 MHz, CDC13, 25 °C) 0 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, CDC13, 25°C) ô 151.6, 148.4, 134.2, 129.0, 126.5, 20.8, 18.1. MS-HR (ESI) m / z calculated for Ci6H13F5N [M+H]+ 314.0963, found: 314.0957.

[0595] EXAMPLE 2: Synthesis of the (Eï-N- (2-ethvlphenvl) -1 - (pentafluorophenvDmethanimine

[0596] [Chem. 130]

[0597] 2-Ethylaniline (2.0 mL, 16.5 mmol) is added to a solution of perfluorobenzaldehyde (1.8 mL, 15 mmol) in EtOH (10 mL) at 25 °C and the solution is then refluxed (90 °C) for 16 h. After evaporation of the solvent and recrystallization in ether at -20 °C, (E)-A-(2-ethylphenyl)-l-(pentafluorophenyl)methanimine (3.7 g, 13.3 mmol, 82%) is obtained as yellow crystals. 'H NMR (360 MHz, CDC13, 25 °C) ô 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). 13C NMR (90 MHz, CDC13, 25°C) ô 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 Ci5HnF5N [M+H]+ 300.0806, found: 300.0799.

[0598] EXAMPLE 3: Synthesis of (Æ')-2.3.4.5-tetrafluoro-Æ -mesitvl-6-((mesitvlimino)methvl)aniline

[0599] [Chem. 131]

[0600] (E)-A-mesityl-l-(perfluorophenyl)methanimine (2.5 g, 8 mmol) is added to a solution of lithium (2,4,6-trimethylphenyl)amide (2.8 g, 20 mmol) in toluene (16 mL) and then stirred for 48 h at 25°C. After the addition of a saturated NaHCO3 solution (50 mL), the aqueous phase is extracted with EtOAc (50 mL). The organic phases are collected, dried over MgSO4, filtered, and concentrated under reduced pressure. Recrystallization in MeOH at -20°C is carried out and gives pale yellow crystals of the product (£')-2,3,4,5-tetrafluoro-A-mesityl-6-((mesitylimino)methyl)aniline (3.3 g, 7.7 mmol, 96%) *H NMR (360 MHz, CDC13, 25 °C) 0 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). 13C {19F} NMR (100 MHz, CDC13, 25°C) ô 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.

[0601] EXAMPLE 4: Synthesis of (Eï-N - (2-ethvlphenvl) -2-((( 2-ethvlphenvl)imino)methvl) -3.4.5.6-tetrafluoroaniline

[0602] [Chem. 132]

[0603] (E)-N-(2-ethylphenyl)-l-(pentafluorophenyl)methanimine (2.4 g, 8 mmol) is 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 a saturated solution of NaHCO3 (50 mL), the aqueous phase is extracted with EtOAc (50 mL). The organic phases are collected, dried over MgSO4, filtered, and concentrated under reduced pressure. Recrystallization in MeOH at -20°C gives pale yellow crystals of the product (E)-N-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3,4,5,6-tetrafluoroaniline (2.7 g, 6.75 mmol, 84%). >H NMR (360 MHz, CDC13, 25 °C) ô 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). 13C {I9F] NMR (100 MHz, CDC13, 25°C) ô 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. . EXAMPLE 5: Summary of P5

[0604] [Chem. 133]

[0605] n-BuLi (2.5 M in hexane) (2 mL, 5 mmol) is added with stirring to a A solution of (£)-2,3,4,5-tetrafluoro-A-mesityl-6-((mesitylimino)methyl)aniline (2.1 g, 5 mmol) was added to 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 then extracted with Et₂O (25 mL). The ether solution was filtered, concentrated, and replaced with hexane (20 mL). After adding a few drops of THF and cooling to -20 °C, red-colored crystals of product P5 (2.09 g, 3.0 mmol, 60%) were obtained. Elemental analysis calculated for C25H23Cl2F4FeLiN2(C4H8O)2: C, 56.19; H, 5.57; N, 3.97, found: C, 54.53; H 5.92; No. 4.15. 'H NMR (360 MHz, C6D6-50 pL THF-d8, 25 °C) ô ppm 71.05 (s, 3H, p-Me), 33.95 (s, 3H, p-Me), 25.51 (s, 2H, mH Ar), 24.01 (br s, 6H, o-Me), 14.16 (s, 2H, mH Ar), 4.37 (br s, 12H, THF), 2.15 (br s, 6H, o-Me), 1.69 (br s, 12H, THF). 7Li NMR (117 MHz, C6D6-50pL THF-d8, 25 °C) ô ppm 239.6 (br s). . EXEMPLE 6 : Synthèse de P6

[0606] [Chem. 134]

[0607] n-BuLi (2.5 M in hexane) (2 mL, 5 mmol) is 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 is removed 30 minutes after the addition. The solution is stirred for 4 h at 25 °C. Then, FeCl2 (0.63 g, 5 mmol) is added. The solution is stirred overnight, and then the solvent is evaporated under reduced pressure. The residual solid is washed with hexane or pentane (10 mL) and then extracted with Et2O (25 mL). The ether solution is filtered, then concentrated and replaced with hexane (20 mL). After adding a few drops of THF and cooling to -20°C, red-colored crystals of product P6 (1.1 g, 1.6 mmol, 35%) are obtained. Elemental analysis calculated for C23Hi9Cl2F4FeLiN2(C4H8O)2: C, 54.97; H, 5.21; N, 4.14; found: C, 51.13; H, 4.90; N, 4.40. 1H NMR (250 MHz, C6D6-50 pL THF-d8, 25 °C) 0 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). EXEMPLE 7 : Synthèse de P7

[0608] [Chem. 135]

[0609] n-BuLi (2.5 M in hexane) (2.8 mL, 7 mmol) is 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 is removed 30 minutes after the addition. The solution is stirred for 4 h at 25 °C and concentrated under reduced pressure to give the lithium amide of (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesitylimino)methyl)aniline. To a solution of Fe(acac)3 (2.1 g, 6 mmol) in THF (12 mL), lithium amide of (E)-2,3,4,5-tetrafluoro-A-mesityl-6-((mesitylimino)methyl)aniline (2.6 g, 6 mmol) in THF (6 mL) is added while stirring at 25 °C. The solution is then stirred for 16 hours at the same temperature. The red-colored solution turns dark green. After cooling to -20 °C, filtration through Celite and evaporation are performed. The solid is washed with cold pentane to yield a dark green powder, product P7 (2 g, 2.9 mmol, 50%).Elemental analysis calculated for C35H37F4FeN2O4: C, 61.68 H, 5.47; N, 4.11, found: C, 59.9; H 5.39; N 3.92. >H NMR (250 MHz, C6D6-50 pL THF-d8 25 °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.

[0610] [Chem. 136]

[0611] n-BuLi (2.5 M in hexane) (0.8 mL, 2.0 mmol) is 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 is removed 30 minutes after the addition. The solution is stirred for 4 h at 25 °C. Then, FeBr2 (0.389 g, 1.8 mmol) is added. The solution is stirred overnight, and then the solvent is evaporated under reduced pressure. The residual solid is washed with hexane or pentane and then extracted with Et2O. The ether solution is filtered, then concentrated and replaced with hexane. After adding a few drops of THF and cooling to -20°C, red-colored crystals of product P8 (0.63 g, 0.8 mmol, 44%) are obtained. 'H NMR (250 MHz, C6D6-50 pL THF-d8, 25 °C) 0 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).7Li NMR (117 MHz, C6D6-50pL THF-d8, 25 °C) ô ppm 162.66 (br s). .

[0612] EXAMPLE 9: Byers synthesis of phenylcycloheptane (reference example)

[0613] [Chem. 137]

[0614] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of phenylboronic acid (2 eq) in benzene (c = 0.5 M) is added to EtNMeLi (1.2 eq) and to the Byers catalyst (Angew. Chem., Int. Ed. 2020, 59, 5392) (10 mol%).

[0615] [Chem. 138]

[0616] 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 The total bromocycloheptane concentration was 0.08 M. The reaction mixture was stirred at 25 °C for 5 h, and then a saturated aqueous solution of NH4Cl was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered, and evaporated under reduced pressure. Gas chromatography analysis using dodecane as the internal standard yielded phenylcycloheptane with a 94% yield. EXAMPLE 10: Synthesis A of phenylcycloheptane

[0617] [Chem. 139] k 7

[0618] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 brought to a total bromocycloheptane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 4 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 chromatography using dodecane as an internal standard yielded phenylcycloheptane with a yield of >99%. Silica gel column chromatography was performed, yielding phenylcycloheptane with a yield of 95%.'H NMR (400 MHz, CDC13, 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). 13C NMR (100 MHz, CDC13, 25°C) (mixture with dodecane) δ 150.0, 128.3, 126.7, 125.5, 47.0, 36.8, 28.0, 27.2.

[0619] The yield is higher than that obtained with the Byers catalyst and the reaction is faster. EXAMPLE 11: Synthesis B of phenylcycloheptane

[0620] [Chem. 140]

[0621] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of phenylboronic acid (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 a total bromocycloheptane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 24 h (not optimized time), 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. ¹H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gives phenylcycloheptane with >99% yield. EXAMPLE 12: C synthesis of phenylcycloheptane

[0622] [Chem. 141] ky

[0623] 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 pinacolic phenylboronic acid 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 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 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives phenylcycloheptane with 89% yield. EXAMPLE 13: Synthesis D of phenylcycloheptane

[0624] [Chem. 142] ry L . /

[0625] 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 pinacolic ester of phenylboronic acid (2 eq) in benzene (c = 0.5 M) is added to catalyst P7 (10 mol%) and to EtNMeLi (2.2 eq). A bro- solution Bro-mocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then brought to a total concentration of 0.08 M bro-mocycloheptane. 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. ¹H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gives phenylcycloheptane with an 87% yield.

[0626] 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. EXAMPLE 14: Synthesis E of phenylcycloheptane

[0627] [Chem. 143]

[0628] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 to 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 chromatography analysis using dodecane as an internal standard gives phenylcycloheptane with >99% yield.

[0629] The yield is higher than that obtained with the Byers catalyst and the reaction is faster. EXAMPLE 15: Synthesis A of octylbenzene

[0630] [Chem. 144]

[0631] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of phenylboronic acid (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and to 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 brought to a total concentration of 0.08 M to obtain a total 1-bromooctane concentration. 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, yielding octylbenzene in 71% of its original concentration. 'H NMR (400 MHz, CDC13, 25°C) ô 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, CDC13, 25°C) ô 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. EXAMPLE 16: Synthesis B of octylbenzene

[0632] [Chem. 145]

[0633] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 a total 1-bromooctane concentration of 0.08 M. The reaction mixture is stirred at 25 °C for 29 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 was performed and gave octylbenzene with a 91% yield. 'H NMR (400 MHz, CDC13, 25°C) ô 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, CDC13, 25°C) ô 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. EXAMPLE 17: Synthesis of l-methyl-4-octylbenzene.

[0634] [Chem. 146]

[0635] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of toluylboronic acid (2 eq) in benzene (c = 0.5 M) is

[0636] 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 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. ¹H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gives 1-methyl-4-octylbenzene with a 99% yield. Silica gel column chromatography was performed and yielded 1-methyl-4-octylbenzene with a 76% yield. ¹³C NMR (360 MHz, CDC13, 25°C) yields: 7.15-7.10 ppm (m, 4H), 2.61 ppm (t, J=7.6 Hz, 2H), 2.37 ppm (s, 3H), 1.66-1.60 ppm (m, 2H), 1.35-1.32 ppm (m, 10H), 0.93 ppm (t, J=6.8 Hz, 3H). ¹³C NMR (360 MHz, CDC13, 25°C) yields: 139.9 ppm, 134.9 ppm, 128.9 ppm, 128.3 ppm, 35.5 ppm, 31 ppm.9, 31.7, 29.5, 29.4, 29.3, 22.7, 21.0, 14.1. . EXAMPLE 18: Synthesis of l-methoxy-4-octylbenzene [Chem. 147] CH 3 17

[0637] 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 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. An analysis by 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives l-methoxy-4-octylbenzene with 99% yield. Silica gel column chromatography is performed and gives l-methoxy-4-octylbenzene with 76% yield 'H NMR (360 MHz, CDC13, 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). 13C NMR (360 MHz, CDC13, 25°C) ô 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 C15H25O [M+H]+, 221.1900, found: 221.1756. . EXAMPLE 19: Synthesis of l-phenoxy-4-octylbenzene

[0638] [Chem. 148]

[0639] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of 4-phenoxyphenylboronic 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 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. An analysis by 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives l-phenoxy-4-octylbenzene with 99% yield.

[0640] EXAMPLE 20: Synthesis of ÆJV-dimethyl-4-octylaniline

[0641] [Chem. 149] ch3

[0642] The reaction is carried out under an inert atmosphere in a glove box. A pinacolic ester solution of 4-(dimethylamino)phenylboronic acid (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A 1-bromooctane solution (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then brought to a total concentration of 0.08 M 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. Silica gel column chromatography was performed and yielded A,A-dimethyl-4-octylaniline with a 90% yield. 'H NMR (360 MHz, CDC13, 25°C) ô ppm 7.12 (d, J= 8.7 Hz, 2H), 6.75 (d, J= 8.7 Hz, 2H), 3.96 (s, 6H), 2.57 (t, J= 7.6 (t. 3, 2H), 2H), 1.36–1.33 (m, 10H), 0.94 (t, J= 6.8 Hz, 3H). 13C NMR (90 MHz, CDC13, 25°C) at ppm 148.9, 131.23, 128.90, 113.0, 40.9, 34.9, 31.9, 29.5, 29.3, 22.1.7. MS-HR (ESI) m / z calculated for Cj6H28N [M+H] + 234.2216, found: 234.2213. EXAMPLE 21 Synthesis of l-chloro-4-octylbenzene.

[0643] [Chem. 150]

[0644] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of 4-chlorophenylboronic 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 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 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gives l-chloro-4-octylbenzene with a 40% yield. EXAMPLE 22: Synthesis of l-nitro-4-octylbenzene

[0645] [Chem. 151] O

[0646] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of 4-nitrophenylboronic 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 brought up to a total concentration of 0.08 M 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. An analysis by 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives l-nitro-4-octylbenzene with 36% yield. EXAMPLE 23: Synthesis of l-fluoro-4-octylbenzene

[0647] [Chem. 152]

[0648] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of 4-fluorophenylboronic 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 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 was performed and gave 1-fluoro-4-octylbenzene with 88% yield. 'H NMR (360 MHz, CDC13, 25°C) ô ppm7.16-7.11 (m, 2H), 7.01-6.94 (m, 2H), 2.59 (t, J= 7.6 Hz, 2H), 1.61 (qui, J= 7.4 Hz, 2H), 1.33-1.30 (m, 10H), 0.91 (t, J= 6.7 Hz, 3H).13C NMR (90 MHz, CDC1 3, 25°C) ô 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. .

[0649] EXAMPLE 24: Synthesis of l-octyl-3-(trifluoromethyl)benzene

[0650] [Chem. 153]

[0651] The reaction is carried out under an inert atmosphere in a glove box. A pinacolic ester solution of 3-trifluoromethylphenylboronic acid (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A 1-bromooctane solution (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then brought up to a total concentration of 0.08 M of 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. Silica gel column chromatography is performed and gives l-octyl-3-(trifluoromethyl)benzene with 83% yield. 'H NMR (360 MHz, CDC13, 25°C) 0 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 NMR (90 MHz, CDC13, 25°C) ô 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= 3.7Hz), 35.8, 31.9, 31.3, 29.4, 29.2, 22.7, 14.1.

[0652] EXAMPLE 25: Synthesis of benzyl 4-phenylpiperidine-l-carboxylate

[0653] [Chem. 154]

[0654] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 brought to 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 was performed and gave benzyl 4-phenylpiperidine-l-carboxylate with a 95% yield. 'H NMR (360 MHz, CDC13, 25°C) 0 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). 13C NMR (90 MHz, CDC1 3, 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 calculated for Ci9H22NO2 [M+H]+ 296.1645, found: 296.1638. EXAMPLE 26: Synthesis A of 1-phenyladamantane.

[0655] [Chem. 155]

[0656] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 to 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 was performed and yielded 1-phenyladamantane with a 98% yield. ¹³C NMR (360 MHz, CDC13, 25°C) µm: 7.41-7.32 ppm (m, 4H), 7.23-7.18 ppm (m, 1H), 2.13 ppm (m, 3H), 1.96-1.95 ppm (m, 6H), 1.85-1.75 ppm (m, 6H). ¹³C NMR (90 MHz, CDC13, 25°C) µm: 151.3 ppm, 128.1 ppm, 125.5 ppm, 124 ppm.8, 43.1, 36.8, 28.9. . EXAMPLE 27: Synthesis B of 1-phenyladamantane

[0657] [Chem. 156]

[0658] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 brought to 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 was performed and yielded 1-phenyladamantane with a 79% yield. ¹³C NMR (360 MHz, CDC13, 25°C) µm: 7.41-7.32 ppm (m, 4H), 7.23-7.18 ppm (m, 1H), 2.13 ppm (m, 3H), 1.96-1.95 ppm (m, 6H), 1.85-1.75 ppm (m, 6H). ¹³C NMR (90 MHz, CDC13, 25°C) µm: 151.3 ppm, 128.1 ppm, 125.5 ppm, 124 ppm.8, 43.1, 36.8, 28.9. . EXAMPLE 28: Synthesis of 2-octylthiophene

[0659] [Chem. 157]

[0660] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of 2-thienylboronic 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 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 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 2-octylthiophene with 78% yield. EXAMPLE 29: Synthesis of 6-cycloheptylquinoline

[0661] [Chem. 158]

[0662] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of 6-quinolineboronic acid (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 a total bromocycloheptane 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. Silica gel column chromatography was performed and gave 2-octylthiophene with an 88% yield. 'H NMR (360 MHz, CDC13, 25°C) 0 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). 13C NMR (90 MHz, CDC13, 25°C) ô 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. EXAMPLE 30: Synthesis of 1,1'-methylenedibenzene

[0663] [Chem. 159]

[0664] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 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. A 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gives 1,1'-methylenedibenzene with a 30% yield. EXAMPLE 31: Synthesis of 2-octylnaphthalene

[0665] [Chem. 160] ri3U g

[0666] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of naphthylboronic 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 brought to a total concentration of 0.08 M benzene. 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 was performed and gave 2-octylnaphthalene with a 93% yield. 1H NMR (400 MHz, CDC13, 25°C) 0 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). 13C NMR (100 MHz, CDC13, 25°C) ô 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. EXAMPLE 32: Synthesis of hexylbenzene

[0667] [Chem. 161]

[0668] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 to 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 MgSO4, filtered, and evaporated under reduced pressure. Silica gel column chromatography was performed and yielded hexylbenzene with a 90% yield. ¹³C NMR (360 MHz, CDC13, 25°C) µm: 7.22-7.17 ppm (m, 2H), 7.11-7.07 ppm (m, 3H), 2.53 ppm (t, J=7.6 Hz, 2H), 1.58-1.49 ppm (m, 2H), 1.28-1.20 ppm (m, 6H), 0.81 ppm (t, J=6.8 Hz, 3H). ¹³C NMR (90 MHz, CDC13, 25°C) µm: 143 ppm.0, 128.4, 128.2, 125.5, 36.0, 31.7, 31.5, 29.0, 22.6, 14.1. . EXAMPLE 33: Synthesis A of cyclopropylbenzene

[0669] [Chem. 162]

[0670] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 brought to 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. An ¹H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gives cyclopropylbenzene with a 45% yield. EXAMPLE 34: Synthesis B of cyclopropylbenzene

[0671] [Chem. 163] / / A (7

[0672] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 brought to 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. An analysis by 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives cyclopropylbenzene with a 26% yield. EXAMPLE 35: Synthesis of 3-phenyloxetane

[0673] [Chem. 164]

[0674] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 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. A 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gives 3-phenyloxetane with a 69% yield. Silica gel column chromatography is performed and gives hexylbenzene with a 58% yield. 1H NMR (360 MHz, CDC13, 25°C) 0 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). 13C NMR (90 MHz, CDC13, 25°C) ô ppm 141.5, 128.8, 127.0, 126.8, 78.9, 40.4. . EXAMPLE 36: Synthesis A of tert-butylbenzene

[0675] [Chem. 165]

[0676] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 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. An analysis by 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives tert-butylbenzene with a 54% yield. EXAMPLE 37: Synthesis B of tert-butylbenzene

[0677] [Chem. 166]

[0678] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 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. An analysis by 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives tert-butylbenzene with a 32% yield. EXAMPLE 38: Synthesis of 2-cycloheptylthiophene

[0679] [Chem. 167]

[0680] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic ester of 2-thienylboronic acid (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 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. ¹H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard yielded 2-cycloheptylthiophene with an 86% yield. Silica gel column chromatography was performed, yielding 2-cycloheptylthiophene with a 78% yield. ¹H NMR (250 MHz, CDC13, 25°C) ± 7 ppm.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). 13C NMR (63 MHz, CDC13, 25°C) ô ppm 153.6, 126.3, 122.0, 121.7, 41.6, 37.5, 28.1, 26.3. .

[0681] EXAMPLE 39: Synthesis of tert-butyl 4-(5-cycloheptylpyridin-2-yl)piperazine-l-carboxylate

[0682] [Chem. 168]

[0683] The reaction is carried out under an inert atmosphere in a glove box. A pinacolic ester solution of l-tert-butyl-4-(pyridin-2-yl)piperazineboronic acid (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and to 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 a total chlorocycloheptane 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, yielding tert-butyl 4-(5-cycloheptylpyridin-2-yl)piperazine-l-carboxylate in 92% yield. 'H NMR (360 MHz, CDC13, 25 °C) ô 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). 13C NMR (90 MHz, CDC13, 25 °C) ô 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 C2iH34N3O2 [M+H]+ 360.2646, found: 360.2629. .

[0684] EXAMPLE 40: Synthesis of the term M>utyldimethyl(3-phenylpropoxy)silane

[0685] [Chem. 169]

[0686] The reaction is carried out under an inert atmosphere in a glove box. A solution of pinacolic phenylboronic acid 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 brought to 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 was performed and gave tert-butyldimethyl(3-phenylpropoxy)silane with a 78% yield. 'H NMR (360 MHz, CDC13, 25°C) 0 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). 13C NMR (90 MHz, CDC13, 25°C) or ppm 142.3, 128.5, 128.31, 125.7, 62.4, 34.5, 32.2, 26.0, 18.4, −5.2. . EXAMPLE 41 Synthesis of cyclopentylbenzene A

[0687] [Chem. 170]

[0688]

[0689] 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 brought to 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 ¹H NMR using 1,3,5-trimethoxybenzene as an internal standard gives cyclopentylbenzene with a 99% yield. Silica gel column chromatography is performed and gives cyclopentylbenzene with a 70% yield. ¹H NMR (360 MHz, CDC13, 25°C) µ 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 RMN (90 MHz, CDC13, 25°C) ô ppm 146.5, 128.2, 127.1, 125.6, 45.9, 34.6, 25.5. . EXEMPLE 42 : Synthèse B du cyclopentylbenzène [Chem. 171]

[0690] 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 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 ¹H NMR using 1,3,5-trimethoxybenzene as an internal standard gives cyclopentylbenzene with 99% yield.

[0691]

[0692]

[0693]

[0694]

[0695]

[0696] (360 MHz, CDC13, 25°C) ô 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 RMN (90 MHz, CDC13, 25°C) ô ppm 146.5, 128.2, 127.1, 125.6, 45.9, 34.6, 25.5. EXEMPLE 43 : Synthèse C du cyclopentylbenzène [Chem. 172] 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 iodoocy-clopentane (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then brought to a total concentration of 0.08 M iodocy-clopentane. 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 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives cyclopentylbenzene with a 77% yield. P5 can catalyze the formation of carbon-carbon bonds with previously defined brominated, chlorinated, or iodinated halogenated Z-Hal derivatives. EXAMPLE 44: Synthesis of tert-butyl 3-phenylazetidine-l-carboxylate [Chem. 173] 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-l-carboxylate (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then brought to a total concentration of 0.08 M tert-butyl 3-bromoazetidine-l-carboxylate. 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. An analysis by 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives tert-butyl 3-phenylazetidine-l-carboxylate with >99% yield. Silica gel column chromatography was performed and gave tert-butyl 3-phenylazetidine-l-carboxylate with 83% yield. 'H NMR (360 MHz, CDC13, 25°C) 0 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). 13C NMR (90 MHz, CDC13, 25°C) ô ppm 156.4, 142.2, 128.7, 126.9, 126.7, 79.5, 33.5, 28.4. MS-HR (ESI) m / z calculated for C14 H20NO2 [M+H]+ 234.1489, found: 234.1482.

[0697] EXAMPLE 45: Synthesis of 2-octyl-l-tosyl-lH-indole

[0698] [Chem. 174]

[0699] The reaction is carried out under an inert atmosphere in a glove box. A pinacolic ester solution of (l-tosyl-lH-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 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. An analysis by 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 2-octyl-l-tosyl-lH-indole with 62% yield.

[0700] EXAMPLE 46: Synthesis of tert-butvl 2-octvl-lH-indole-l-carboxvlate

[0701] [Chem. 175]

[0702] The reaction is carried out under an inert atmosphere in a glove box. A pinacolic ester solution of (l-(tert-butoxycarbonyl)-lH-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 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,

[0703] The samples were filtered and evaporated under reduced pressure. ¹H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard yielded tert-butyl 2-octyl-1H-indole-1-carboxylate in 82% of the yield. Silica gel column chromatography was performed, yielding tert-butyl 2-octyl-1H-indole-1-carboxylate in 50% of the yield. 'H NMR (300 MHz, CDC13, 25°C) ô 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). 13C NMR (75 MHz, CDC13, 25°C) ô 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. EXAMPLE 47: Synthesis of 2-octyl-l-benzofuran [Chem. 176]

[0704] The reaction is carried out under an inert atmosphere in a glove box. A pinacolic ester solution of 2-benzofuraneboronic acid (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A 1-bromooctane solution (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then made up to 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 ¹H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 2-octyl-1-benzofuran with an 87% yield. Silica gel column chromatography is performed and gives 2-octyl-1-benzofuran with an 82% yield. ¹H NMR (360 MHz, CDC13, 25°C) µ 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), 1.20H (1.39). J= 7.1 Hz, 3H). 13C NMR (90 MHz, CDC13, 25°C) or ppm 160.0, 154.6, 129.0, 123.0, 122.3, 120.1, 110.7, 101.7, 31.8, 27.2, 29.3, 22.7, 14.1 EXAMPLE 48 Synthesis of 2-octylfurane .

[0705] [Chem. 177]

[0706] The reaction is carried out under an inert atmosphere in a glove box. A pinacolic ester solution of 2-furaneboronic acid (2 eq) in benzene (c = 0.5 M) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A 1-bromooctane solution (1 eq) in benzene (c = 0.25 M) is added to the solution, which is then made up to 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 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives 2-octylfuran with 89% yield. EXAMPLE 49: Synthesis of (3-methylundecyl)benzene

[0707] [Chem. 178] GH

[0708] 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 1.2 equivalents of NMe2Li. 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 a total (3-bromobutyl)benzene 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 (3 x 40 mL), the combined organic phases are dried over MgSO4, filtered, and evaporated under reduced pressure. Silica gel column chromatography was performed and yielded (3-methylundecyl)benzene with an 86% yield. NMR (300 MHz, CDC13, 25°C) α ppm 7.33-7.28 (m, 2H), 7.22-7.17 (m, 3H), 2.73-2.64 (m, 1H), 2.62-2.54 (m, 1H), 1.70-1.61 (m, 1H), 1.53-1.44 (m, 2H), 1.30 (brs, 13H), 1.19-1.13 (m, 1H), 0.97-0.90 (m, 6H). 13C NMR (75 MHz, CDC13, 25°C) ô ppm 143.2, 128.3, 128.2, 125.5, 39.0, 36.9, 33.51, 32.5, 31.9, 30.0, 29.7, 29.4, 27.0, 22.7, 19.6, 14.1.

[0709] EXAMPLE 50: Synthesis of benzvl 4-(3-DhenvlDroDvl)DiDeridine-l-carboxide

[0710] [Chem. 179] JL > BzC '■■■■'

[0711] 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 brought to 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. A 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gives benzyl 4-(3-phenylpropyl)piperidine-l-carboxylate with 70% yield.

[0712] EXAMPLE 51: Synthesis of tert-butyldimethyl((6-phenylhexyl)oxy)silane

[0713] [Chem. 180]

[0714] 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 brought to 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. 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard yields tert-butyldimethyl((6-phenylhexyl)oxy)silane with a 78% yield.

[0715] EXAMPLE 52: Synthesis of (3-cyclopentylpropyl)benzene

[0716] [Chem. 181]

[0717] 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 brought to a total concentration of 0.08 M bromocyclopentane. 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 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives (3-cyclopentylpropyl)benzene with 59% yield.

[0718] EXAMPLE 53: Synthesis of (3-DhenvlDroDvl)cvcloheDtane

[0719] [Chem. 182]

[0720] 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 brought to 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 'H NMR using 1,3,5-trimethoxybenzene as an internal standard gives (3-phenylpropyl)cycloheptane with 59% yield.

Claims

1. Demands Use of at least one of the compounds with the following general formula (I): [Chem. 183] (I) in which: A is chosen from: a grouping -X in which X is chosen from a chlorine atom a bromine atom a group [Chem. 184] 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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 such as reactions of Suzuki-Miyaura, Kumada and Sonogashira, in particular for the implementation of the Suzuki-Miyaura reaction.

2. Use, according to claim 1, of at least one of the compounds of the following general formula (I): [Chem. 186] (I) in which: A is chosen from: - a grouping -X in which X is chosen from - a chlorine atom - a bromine atom - a group [Chem. 187] in which: • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can a grouping vary by a value greater than 0 but less than 4 [Chem. 188] 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 [Chem. 189] then Rb, R5, R6, and Rio, 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 atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms • when A corresponds to the grouping -X or to the grouping [Chem. 190] then Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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 is excluded: [Chem. 191]

3. Use, according to claim 1 or 2, of at least one of the compounds of the following general formula (la): [Chem. 192] (there) in which: X is chosen from 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. Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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.

4. Use, according to claim 1 or 2, of at least one of the compounds of the following general formula (Ib): [Chem. 193] (Ib) in which: • X is chosen from - a chlorine atom - 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9, and Rio, 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.

5. Use, according to claim 1 or 2, of at least one of the compounds having the following general formula: [Chem. 194] (THE) in which: B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a

6. 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 • Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio, 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. Use, according to any one of claims 1, 2 or 3, of at least one of the compounds, • of the following general formula: [Chem. 195] (there) in which: X is chosen from a chlorine atom 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. Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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 that : Ri must be different from R5 and / or R2 must be different from R4 R6 is different from Rio 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 • 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: • Ri is different from R5 and / or R2 is different from R4 And • R6 must be identical to R10 and R7 must be identical to R9 Or • R6 is different from Rio and / or R7 is different from R9 And • Ri 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: (there) in which: • X is chosen from a chlorine atom 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. Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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 par- 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, provided that: Ri is identical to R5 R2 is identical to R4 R6 is identical to R10 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: [Chem. 198] (there) in which: X is chosen from a chlorine atom 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 alkoxy 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: Ri must be different from R5 and / or R2 must be different from R4 R6 is different from Rio 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: [Chem. 199] (there) in which: X is chosen from a chlorine atom 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 alkoxy 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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 atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: - Ri is different from R5 and / or R2 is different from R4 - R6 is identical to Rio and R7 is identical to R9 Or - R6 is different from Rio and / or R7 is different from R9 Ri 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: [Chem.200] (there) in which: X is chosen from a chlorine atom 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 alkoxy 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 Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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 that : Ri is identical to R5 R2 is identical to R4 R6 is identical to Rio 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.

7. Use, according to any one of claims 1, 2 or 4, of at least one of the compounds, of the following general formula (Ib): [Chem.201] (Ib) in which: • X is chosen from - a chlorine atom - 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 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. • Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4 R6 must be different from R10 and / or R7 must be 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): [Chem.202] (Ib) in which: X is chosen from a chlorine atom a bromine atom M is a coordinating solvent p is chosen from 1, 2, 3, 4 or a decimal number that can vary by 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, with at least one of the groups B, C, D, or E being different from the others • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: • Ri is different from R5 and / or R2 is different from R4 And • R6 is identical to Rio and R7 is identical to R9 Or • R6 is different from Rio and / or R7 is different from R9 And • Ri 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): [Chem.203] (Ib) in which: • X is chosen from a chlorine atom 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 Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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: Ri is identical to R5 R2 is identical to R4 R6 is identical to R10, 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): [Chem.204] (Ib) in which: X is chosen from a chlorine atom 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 alkoxy 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 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: Ri must be different from R5 and / or R2 must be different from R4 R6 must be different from R10 and / or R7 must be 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): [Chem.205] (Ib) in which: X is chosen from a chlorine atom 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 alkoxy 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 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: - Ri is different from R5 and / or R2 is different from R4 - R6 is identical to R10 and R7 is identical to R9 Or - R6 must be different from R10 and / or R7 must be different from R9 Ri 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): [Chem.206] (Ib) in which: X is chosen from a chlorine atom 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 alkoxy 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 • Rb, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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: - Ri is identical to R5 - R2 is identical to R4 - R6 is identical to R10 - 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.

8. Use, according to any one of claims 1, 2 or 5, of at least one of the compounds of the following general formula: [Chem.207] (THE) 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: Ri must be different from R5 and / or R2 must be different from R4 R6 must be different from R10 and / or R7 must be 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 with 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 Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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: - Ri is different from R5 and / or R2 is different from R4 - R6 is identical to R10 and R7 is identical to R9 Or - R6 must be different from R10 and / or R7 must be different from R9 Ri 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: (THE) 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. Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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: Ri is identical to R5 R2 is identical to R4 R6 is identical to Rio 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: (THE) in which: B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoro- group romethyl 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: Ri must be different from R5 and / or R2 must be different from R4 R6 must be different from R10 and / or R7 must be 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: [Chem.211] (THE) 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 alkoxy 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 Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio 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: Ri must be different from R5 and / or R2 must be different from R4 - R6 is identical to Rio and R7 is identical to R9 Or - R6 is different from Rio and / or R7 is different from R9 Ri 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: [Chem. 212] (THE) 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 alkoxy 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio 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: Ri is identical to R5 R2 is identical to R4 R6 is identical to R10 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.

9. Use, according to any one of claims 1 to 5, of at least one of the compounds of the following general formula: [Chem.213] (there) in which: • X is chosen from a chlorine atom a bromine atom B, C, D and E are fluorine atoms Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio, 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): [Chem. 214] (Ib) in which: • X is chosen from - a chlorine atom - 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 • Rb R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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: [Chem.215] (THE) in which: B, C, D and E are fluoride atony Ri, R2, R3, R4, R5, Re, R7, Rs, R9 and Rio, 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.

10. Use of the compounds of formula (I), according to any one of the claims

11. 1 to 5, chosen from: [Chem.216] ^FaYY^Aî '"'A..... (O, ÿ--^ W" Y ' [Chem.217] rh' -Ô-C. F / —“\ A—C Y----. Ô ' X- p — " / a V-- / v Compound, of the following general formula (I): [Chem.218] R9 r2 , 1 R10 ' U> ••J< X fi V :;::t T ï i- LJ. Y yk 0 [ U (I) A is chosen from: - a grouping -X in which X is chosen from - a chlorine atom - a bromine atom a group [Chem.219] 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 grouping 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 [Chem.36] then Rb, R5, R6, and R10, 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 atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms • when A corresponds to the grouping -X or to the grouping [Chem.221] then Rb R2, R3, R4, R5, R6, R7, R8, R9 and R10, 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 is excluded: [Chem.222]

12. Compound, according to claim 11 • of the following general formula (I): [Chem.223] (I) in which: • A,, Rb R2, R3, R4, R5, R6, R7, R8, R9, Rio and G have the signi fications 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): [Chem.224] in which: • A, X, M, p, Rb R2, R3, R4, R5, R6, R7, R8, R9, Rio 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 a halogen, in particular F or the following general formula (I): [Chem.225] (I) in which • A, X, M, p, Ri, R2, R3, R4, R5, R6, R7, R8, R9, Rio and G have the meanings given in claim 11 • B, C, D, and E are fluorine atoms

13. Compound • of the following general formula: [Chem.226] (there) in which: X is chosen from a chlorine atom 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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: [Chem.227] (there) 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 alkoxy 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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: Ri must be different from R5 and / or R2 must be different from R4 And R6 must be different from R10 and / or R7 must be different from R9 or the following general formula: [Chem.228] (there) 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 alkoxy 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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: Ri is identical to R5 R2 is identical to R4 R6 is identical to R10 R7 is identical to R9 or the following general formula (Ib): [Chem.229] (Ib) in which: X is chosen from a chlorine atom 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 Rb, R5, R6, and Rio, 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 with 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 is excluded: or the following general formula (Ib): (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 alkoxy 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 Rb, R5, R6, and Rio 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 atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri must be different from R5 and / or R2 must be different from R4 R6 must be different from R10 and / or R7 must be different from R9 [Chem.232] (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 alkoxy 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 Rb, R5, R6, and Rio 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 alkoxy 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 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, provided that: Ri is identical to R5 R2 is identical to R4 R6 is identical to R10 R7 is identical to R9 the compound of the following formula being excluded: [Chem.233]

14. Compound • of the following general formula: (THE) 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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: [Chem.235] (THE) in which: 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 D is identical to C. R2, R3, R4, R5, R6, R7, Rs, R9, and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoro- romethyl 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, provided that: Ri is identical to R5 R2 is identical to R4 R6 is identical to R10 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: [Chem.236] (THE) 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 alkoxy 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. Rb, R2, R3, R4, R5, R6, R7, Rs, R9, and Rio 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 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,provided that: Ri must be different from R5 and / or R2 must be different from R4 R6 is identical to Rio and R7 is identical to R9 R6 is different from Rio and / or R7 is different from R9 Ri 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 atoms

15. A compound of formula (I) according to any one of claims 11 to 14 selected from: [Chem.237]

16. Use of at least one of the compounds of formulas (la), (Ib) or (le) according to any one of claims 1 to 15 for carrying out a Suzuki-Miyaura reaction from a compound (SI) [Chem.238] (IF) 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 group -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 2-furanyl group a 2-naphthyl group a 6-quinolyl 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 and V is chosen from: - a group a group in which q is equal to 0 or 1. 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 a cyclic group of 3 to 12 carbon atoms, in particular an octyl, hexyl or cycloheptyl group - an 1-adamantyl group with the formula a benzyl group of formula a group a group a group a group Bac a group a group and Hal is chosen from among: a chlorine atom, a bromine atom, an iodine atom

17. A method for preparing a compound of formula (la), according to claim 13 (there) in which: X is chosen from a chlorine atom 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 Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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): [Chem.253] in which Rb R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) [Chem.260] (HD in which B, C, D, E, G, Rb, 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): [Chem.261] in which R6, R7, R8, R9, and Rio have the meanings indicated above to obtain the compound of formula (II) [Chem.261] in which B, C, D, E, G, Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and R10 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).

18. Method for preparing a compound of formula (Ib), according to claim 13 (Ib) in which: • X is chosen from - a chlorine atom - 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 10 carbon atoms • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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) [Chem.263] O it (V) in which B, C, D, and E have the meanings indicated above, and F is a fluorine atony on a compound of formula (VI): [Chem.264] in which R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) [Chem.265] (HD in which B, C, D, E, G, Rb, 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 formula (III) on a compound of formula (IV): [Chem 266] (IV) in which R6, R7, R8, R9, and R10 have the meanings indicated above to obtain the compound of formula (II) [Chem.267] in which B, C, D, E, G, Rb, 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 and then of iron (II) halide FeX2 to said compound of formula (II) to obtain the compound of formula (Ib).

19. A method for preparing a compound of formula (the), according to claim 14 (THE) 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 • Rb, R2, R3, R4, R5, R6, R7, Rs, R9 and Rio, 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) [Chem.269] (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): [Chem.270] in which R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) [Chem.271] (HD in which B, C, D, E, G, Rb, 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): [Chem.272] (IV) in which R6, R7, R8, R9, and R10 have the meanings indicated above to obtain the compound of formula (II) [Chem.273] (II) in which B, C, D, E, G, Rb, 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 and then of iron (III) tris-acetylacetonate to said compound of formula (II) to obtain said compound of formula (le).

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