Novel iron-based compounds, process for their preparation and their use as catalysts

Abstract

The present invention relates to iron anilino-imine complexes, to a process for the preparation of said complexes and to the use of said complexes as catalysts in Suzuki-Miyaura reactions.

Description

Technical Field

[0001] The present invention relates to the synthesis of novel iron-based compounds, methods for preparing said compounds and the use of said compounds as catalysts. Background Art

[0002] Iron is a cheap, abundant, readily available and low-toxic metal (Angew. Chem. Int. Ed. 2016, 55, 12150) and tends to replace palladium in the chemical industry. Indeed, from a sustainable development point of view, iron offers many advantages. In addition, iron is one of the few base metals that has been successfully tested as a catalyst in industrial cross-coupling methods on a kilogram scale. Iron β-diketoimine complexes have been used to catalyze hydroamination reactions (Chem. Eur. J. 2019, 25, 835–844). The use of such iron complexes requires working in a "glove box" type device in a controlled atmosphere without humidity and without ambient air (Chem. Eur. J. 2019, 25, 835–844), which constitutes a limiting factor that makes these catalysts difficult to use on an industrial scale.

[0003] Indeed, metal catalysis is a method to accelerate or even enable certain reactions and to obtain large quantities of compounds at production costs far lower than conventional organic synthesis routes, which sometimes require a large number of steps. In addition, the requirement for residual metals in products intended for human use, in particular in products for pharmaceutical use, currently constitutes an obstacle to the use of metal catalysis in the manufacture of such products.

[0004] The development of carbon-carbon bond forming reactions by cross-coupling is one of the greatest revolutions in the field of synthetic organic chemistry. Among the different types of cross-coupling, Suzuki-Miyaura coupling (Angew. Chem., Int. Ed. 2011, 50, 6722) is the coupling between halogenated or pseudo-halogenated organic derivatives and organic boron, palladium catalyzed derivatives, and the Suzuki-Miyaura coupling is one of the most commonly used strategies for forming carbon-carbon bonds in the pharmaceutical industry, agrochemical industry and fine chemicals industry (Adv. Synth. Catal. 2009, 351, 3027). For example, in the pharmaceutical industry, nearly 25% of small molecule drug synthesis uses Suzuki-Miyaura coupling, and the Suzuki-Miyaura coupling accounts for 40% of carbon-carbon bond forming reactions, while other cross-coupling reactions account for less than 5%. Indeed, this coupling is mainly limited to two sp-carrying groups. 2Indeed, the Pd(II)-alkyl intermediates formed during the coupling reaction are easily eliminated, which hinders its general extension to sp-carrying molecules. 3 Hybridized carbon coupling partners. Molecules with more complex three-dimensional geometries that can be obtained by palladium catalysis are very rare, and even fewer when they contain aromatic heterocyclic units, which is problematic because nearly 70% of drug molecules contain at least one heterocycle (Bioactive Heterocyclic Compound Classes: Pharmaceuticals, Wiley, Weinheim, 2012). In addition, although C(sp 3 )-C(sp 3 ) bonds are abundant in natural or biologically active molecules, but in the Suzuki-Miyaura reaction described so far, the sp 3 The coupling between the two partners of hybridized carbon accounts for only 1%.

[0005] Furthermore, the ligands commonly used in industry to stabilize these catalysts are phosphorus-based ligands. Since nitrogen is more abundant than phosphorus, chemists have turned to the design of nitrogen-based ligands, as this is an advantage from a sustainability perspective. Although some examples of iron-based catalysts for Suzuki-Miyaura coupling have been described in the prior art, few have been reported for sp-carrying 3 The coupling partners of hybridized carbon are effective. In addition, they usually rely on the use of activated boron derivatives (using organolithium or organomagnesium), which show significant limitations in terms of functional compatibility, and they use catalysts with phosphorus-based ligands. In addition, there are few examples of coupling with tertiary halides. The latter are usually halides that are difficult to couple due to their steric hindrance.

[0006] The object of the present invention is to solve the above problems and to generate C(sp 3 )-C(sp 2 ) key and C(sp 3 )-C(sp 3 )key.

[0007] The object of the present invention relates to novel compounds of imino-aniline iron.

[0008] Another object of the present invention is the use of the imino-aniline iron complexes for catalyzing the formation of carbon-carbon bonds, in particular the Suzuki-Miyaura reaction.

[0009] The present invention also aims to provide a catalyst that is stable to ambient air, thereby enabling the formation of carbon-carbon bonds.

[0010] Another object of the present invention is to provide a method for preparing an imino-aniline iron complex which can have advantages in a Suzuki-Miyaura reaction.

[0011] Another object of the present invention is to provide novel compounds prepared using the imino-aniline iron complexes. Summary of the invention

[0012] The present invention relates to the use of at least one compound of the following general formula (I) as a catalyst for a coupling reaction:

[0013]

[0014] in:

[0015] ●A is selected from:

[0016] ■-X group, wherein X is selected from chlorine atom, bromine atom,

[0017] ■Group Wherein: M is a coordinating solvent, p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0018] ■Group

[0019] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0020] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0021] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0022] It has been unexpectedly discovered that imino-aniline iron complexes are able to catalyze the formation of carbon-carbon bonds.

[0023] A may represent X, wherein the group X is selected from a chlorine atom or a bromine atom, X(Li-X)-(M) pand (Acac)2. In the case of groups B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 In the case of steric hindrance, A advantageously represents X.

[0024] When due to B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 When there is slight steric hindrance or no steric hindrance, A advantageously represents XX(Li-X)-(M) p .

[0025] "Coordinating solvent" refers to any solvent that can stabilize the electronic gap of the metal cation by using lone pairs of electrons to provide part of its negative charge. The coordinating solvent is selected from the group consisting of diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran. p can take a value of 1, 2, 3, 4 or a decimal, the decimal can be a value greater than 0 but less than 4, and p is preferably 1.

[0026] When A represents two acetylacetone groups, the compound does not degrade or lose its properties under the influence of ambient air.

[0027] The term "ambient air" refers to the surrounding air naturally present in the atmosphere, the composition of which may vary depending on location or altitude.

[0028] "Straight chain" means that the carbon atoms in the alkyl chain (except the carbon atom at the end of the chain) are all bonded one to another by carbon-carbon bonds, such that each carbon atom has only two carbon-carbon bonds, the carbon atom at the beginning of the chain has a single carbon-carbon bond to the rest of the chain, and the carbon atom at the end of the chain includes only one carbon-carbon bond.

[0029] The term "branched" means that each carbon atom in the alkyl chain may contain 3 to 4 carbon-carbon bonds.

[0030] A "catalyst" is a chemical substance that activates or promotes a chemical reaction, either directly or after being converted by another chemical substance.

[0031] The term "coupling reaction" refers to a carbon-carbon bonding reaction that achieves the association of two carbon units, and includes at least one metal transfer step and at least one reduction elimination step. In particular, the coupling reaction also involves a carbon-carbon bonding reaction that achieves the association of two carbon units, and includes at least one single electron oxidative addition step or one two electron oxidative addition step, at least one metal transfer step and at least one reduction elimination step.

[0032] In a particular embodiment, the invention relates to the use as defined above, using an organoboron or organomagnesium or organozinc or organotin as catalyst for carrying out a reaction selected from carbon-carbon bond forming reactions, in particular for carrying out a Suzuki-Miyaura reaction.

[0033] "Organoboron" refers to an organic compound comprising at least one bond between a carbon atom and a boron atom. For example, but not limited to, organic compounds having a boronic acid functional group or a boric ester functional group may be mentioned.

[0034] By "organomagnesium" it is meant an organic compound comprising at least one bond between a carbon atom and a magnesium atom. For example, as a non-limiting example, we can mention the Grignard reagent.

[0035] The term "organozinc" refers to an organic compound comprising at least one bond between a carbon atom and a zinc atom.

[0036] The term "organotin" refers to an organic compound containing at least one bond between a carbon atom and a tin atom.

[0037] In a particular embodiment, the invention relates to the use as defined above for carrying out a Suzuki-Miyaura reaction, a Kumada reaction and a Sonogashira reaction, in particular for carrying out a Suzuki-Miyaura reaction.

[0038] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (I) as defined above:

[0039]

[0040] in:

[0041] A is selected from:

[0042] --X group, wherein X is selected from chlorine atom and bromine atom;

[0043] -Group Wherein: M is a coordinating solvent, p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0044] -Group

[0045] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0046] ●When A corresponds to the group hour,

[0047] R1, R5, R6 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 or 2 or 4 to 10 carbon atoms, a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group having 2 to 4 carbon atoms), a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 2 to 20 carbon atoms;

[0048] ●When A corresponds to a -X group or a group hour,

[0049] R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0050] ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms;

[0051] Compounds of the following formula are not included:

[0052]

[0053] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ia) as defined above as a catalyst for a coupling reaction:

[0054]

[0055] in:

[0056] ●X is selected from a chlorine atom and a bromine atom;

[0057] ● B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched alkyl group of 2 to 4 carbon atoms), a straight chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched dialkylamino group of 2 to 10 carbon atoms;

[0058] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0059] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0060] Due to B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 This structure corresponds to the steric hindrance around the iron atom.

[0061] To facilitate understanding of the following, we arbitrarily consider three axes of symmetry: axis (I), axis (II) and axis (III), as shown in the figure below.

[0062]

[0063] Axis (I) creates symmetry between C and D and between B and E. Axis (II) contains the carbon carrying R3 and the carbon carrying nitrogen of the same phenyl group and creates symmetry between R1 and R5 and between R2 and R4. Axis (III) contains the carbon carrying R8 and the carbon carrying nitrogen of the same phenyl group and creates symmetry between R6 and R7. 10 Symmetry is created between and between R7 and R9.

[0064] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ib) as defined above as a catalyst for a coupling reaction:

[0065]

[0066] in:

[0067] ●X is selected from a chlorine atom and a bromine atom;

[0068] ●M is the coordinating solvent;

[0069] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0070] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0071] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0072] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0073] Due to B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 This structure corresponds to the absence of steric hindrance or the presence of small steric hindrance around the iron atom.

[0074] The compound having formula (Ib) is preferably as follows:

[0075]

[0076] To facilitate understanding of the following, we arbitrarily consider three axes of symmetry: axis (I), axis (II) and axis (III), as shown in the figure below.

[0077]

[0078] Axis (I) creates symmetry between C and D and between B and E. Axis (II) contains the carbon carrying R3 and the carbon carrying nitrogen of the same phenyl group and creates symmetry between R1 and R5 and between R2 and R4. Axis (III) contains the carbon carrying R8 and the carbon carrying nitrogen of the same phenyl group and creates symmetry between R6 and R7. 10 Symmetry is created between and between R7 and R9.

[0079] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ic) as defined above as a catalyst for a coupling reaction:

[0080]

[0081] in:

[0082] B, C, D and E are identical or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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;

[0083] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0084] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0085] To facilitate understanding of the following, we arbitrarily consider three axes of symmetry: axis (I), axis (II) and axis (III), as shown in the figure below.

[0086]

[0087] Axis (I) creates symmetry between C and D and between B and E. Axis (II) contains the carbon carrying R3 and the carbon carrying nitrogen of the same phenyl group and creates symmetry between R1 and R5 and between R2 and R4. Axis (III) contains the carbon carrying R8 and the carbon carrying nitrogen of the same phenyl group and creates symmetry between R6 and R7. 10 Symmetry is created between and between R7 and R9.

[0088] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ia) as defined above as a catalyst for a coupling reaction:

[0089]

[0090] in:

[0091] ●X is selected from a chlorine atom and a bromine atom;

[0092] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, at least one of the groups B, C, D or E is different from the others;

[0093] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0094] - R1 is different from R5 and / or R2 is different from R4,

[0095] and

[0096] -R6 is different from R 10 and / or R7 is different from R9;

[0097] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0098] This particular embodiment corresponds to a lack of symmetry with respect to axis (I), axis (II) and axis (III).

[0099] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ia) as defined above as a catalyst for a coupling reaction:

[0100]

[0101] in:

[0102] ●X is selected from a chlorine atom and a bromine atom;

[0103] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, at least one of the groups B, C, D or E is different from the others;

[0104] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0105] ■ R1 is different from R5 and / or R2 is different from R4, and R6 is different from R 10 are the same and R7 is the same as R9;

[0106] or

[0107] ■R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4;

[0108] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0109] This particular embodiment corresponds to a lack of symmetry with respect to axis (I) and axis (II), and the presence of symmetry with respect to axis (III).

[0110] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ia) as defined above as a catalyst for a coupling reaction:

[0111]

[0112] in:

[0113] ●X is selected from a chlorine atom and a bromine atom;

[0114] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, at least one of the groups B, C, D or E is different from the others;

[0115] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0116] -R1 is the same as R5,

[0117] -R2 is the same as R4,

[0118] -R6 and R 10 same,

[0119] -R7 is the same as R9;

[0120] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0121] This particular embodiment corresponds to the lack of symmetry about axis (I). It also corresponds to the presence of symmetry about axis (II) and axis (III).

[0122] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ia) as defined above as a catalyst for a coupling reaction:

[0123]

[0124] in:

[0125] ●X is selected from a chlorine atom and a bromine atom;

[0126] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0127] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0128] - R1 is different from R5 and / or R2 is different from R4,

[0129] and

[0130] -R6 is different from R 10 and / or R7 is different from R9;

[0131] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0132] This particular embodiment corresponds to the presence of symmetry about axis (I). It also corresponds to the lack of symmetry about axis (II) and axis (III).

[0133] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ia) as defined above as a catalyst for a coupling reaction:

[0134]

[0135] in:

[0136] ●X is selected from a chlorine atom and a bromine atom;

[0137] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0138] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0139] ■ R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9;

[0140] or

[0141] ■R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4;

[0142] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0143] This particular embodiment corresponds to the presence of symmetry with respect to axis (I) and axis (III). It also corresponds to the lack of symmetry with respect to axis (II).

[0144] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ia) as defined above as a catalyst for a coupling reaction:

[0145]

[0146] in:

[0147] ●X is selected from a chlorine atom and a bromine atom;

[0148] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0149] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0150] -R1 is the same as R5,

[0151] -R2 is the same as R4,

[0152] -R6 and R 10 same,

[0153] -R7 is the same as R9;

[0154] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0155] This particular embodiment corresponds to the existence of symmetry with respect to axis (I), axis (II) and axis (III).

[0156] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ia) as defined above as a catalyst for a coupling reaction:

[0157]

[0158] in:

[0159] ●X is selected from a chlorine atom and a bromine atom;

[0160] ● B, C, D and E are fluorine atoms;

[0161] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0162] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0163] This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl groups carrying the groups B, C, D and E. This has the consequence of modifying the electronic properties of the iron atom of the catalyst.

[0164] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ib) as defined above as a catalyst for a coupling reaction:

[0165]

[0166] in:

[0167] ●X is selected from a chlorine atom and a bromine atom;

[0168] ●M is the coordinating solvent;

[0169] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0170] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, at least one of the groups B, C, D or E is different from the others;

[0171] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0172] - R1 is different from R5 and / or R2 is different from R4,

[0173] and

[0174] -R6 is different from R 10 and / or R7 is different from R9;

[0175] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0176] This particular embodiment corresponds to a lack of symmetry with respect to axis (I), axis (II) and axis (III).

[0177] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ib) as defined above as a catalyst for a coupling reaction:

[0178]

[0179] in:

[0180] ●X is selected from a chlorine atom and a bromine atom;

[0181] ●M is the coordinating solvent;

[0182] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0183] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, at least one of the groups B, C, D or E is different from the others;

[0184] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0185] ■ R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9;

[0186] or

[0187] ■R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4;

[0188] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0189] This particular embodiment corresponds to a lack of symmetry with respect to axis (I) and axis (II), and the presence of symmetry with respect to axis (III).

[0190] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ib) as defined above as a catalyst for a coupling reaction:

[0191]

[0192] in:

[0193] ●X is selected from a chlorine atom and a bromine atom;

[0194] ●M is the coordinating solvent;

[0195] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0196] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, at least one of the groups B, C, D or E is different from the others;

[0197] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0198] -R1 is the same as R5,

[0199] -R2 is the same as R4,

[0200] -R6 and R 10 same,

[0201] -R7 is the same as R9;

[0202] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0203] This particular embodiment corresponds to the lack of symmetry about axis (I). It also corresponds to the presence of symmetry about axis (II) and axis (III).

[0204] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ib) as defined above as a catalyst for a coupling reaction:

[0205]

[0206] in:

[0207] ●X is selected from a chlorine atom and a bromine atom;

[0208] ●M is the coordinating solvent;

[0209] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0210] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0211] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0212] - R1 is different from R5 and / or R2 is different from R4,

[0213] and

[0214] -R6 is different from R 10 and / or R7 is different from R9;

[0215] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0216] This particular embodiment corresponds to the presence of symmetry about axis (I). It also corresponds to the lack of symmetry about axis (II) and axis (III).

[0217] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ib) as defined above as a catalyst for a coupling reaction:

[0218]

[0219] in:

[0220] ●X is selected from a chlorine atom and a bromine atom;

[0221] ●M is the coordinating solvent;

[0222] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0223] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0224] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0225] ■ R1 is different from R5 and / or R2 is different from R4, and R6 is different from R 10 are the same and R7 is the same as R9;

[0226] or

[0227] ■R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4;

[0228] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0229] This particular embodiment corresponds to the presence of symmetry about axis (I) and axis (III). It also corresponds to the lack of symmetry about axis (II).

[0230] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ib) as defined above as a catalyst for a coupling reaction:

[0231]

[0232] in:

[0233] ●X is selected from a chlorine atom and a bromine atom;

[0234] ●M is the coordinating solvent;

[0235] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0236] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0237] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0238] -R1 is the same as R5,

[0239] -R2 is the same as R4,

[0240] -R6 and R 10 same,

[0241] -R7 is the same as R9;

[0242] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0243] This particular embodiment corresponds to the existence of symmetry with respect to axis (I), axis (II) and axis (III).

[0244] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ib) as defined above as a catalyst for a coupling reaction:

[0245]

[0246] in:

[0247] ●X is selected from a chlorine atom and a bromine atom;

[0248] ●M is the coordinating solvent;

[0249] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0250] ● B, C, D and E are fluorine atoms;

[0251] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0252] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0253] This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl groups carrying the groups B, C, D and E. This has the consequence of modifying the electronic properties of the iron atom of the catalyst.

[0254] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ic) as defined above as a catalyst for a coupling reaction:

[0255]

[0256] in:

[0257] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, at least one of the groups B, C, D or E is different from the others;

[0258] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0259] - R1 is different from R5 and / or R2 is different from R4,

[0260] and

[0261] -R6 is different from R 10 and / or R7 is different from R9;

[0262] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0263] This particular embodiment corresponds to a lack of symmetry with respect to axis (I), axis (II) and axis (III).

[0264] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ic) as defined above as a catalyst for a coupling reaction:

[0265]

[0266] in:

[0267] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, at least one of the groups B, C, D or E is different from the others;

[0268] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0269] ■ R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9;

[0270] or

[0271] ■R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4;

[0272] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0273] This particular embodiment corresponds to a lack of symmetry with respect to axis (I) and axis (II), and the presence of symmetry with respect to axis (III).

[0274] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ic) as defined above as a catalyst for a coupling reaction:

[0275]

[0276] in:

[0277] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, at least one of the groups B, C, D or E is different from the others;

[0278] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0279] -R1 is the same as R5,

[0280] -R2 is the same as R4,

[0281] -R6 and R 10 same,

[0282] -R7 is the same as R9;

[0283] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0284] This particular embodiment corresponds to the lack of symmetry about axis (I). It also corresponds to the presence of symmetry about axis (II) and axis (III).

[0285] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ic) as defined above as a catalyst for a coupling reaction:

[0286]

[0287] in:

[0288] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0289] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0290] - R1 is different from R5 and / or R2 is different from R4,

[0291] and

[0292] -R6 is different from R 10 and / or R7 is different from R9;

[0293] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0294] This particular embodiment corresponds to the presence of symmetry about axis (I). It also corresponds to the lack of symmetry about axis (II) and axis (III).

[0295] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ic) as defined above as a catalyst for a coupling reaction:

[0296]

[0297] in:

[0298] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0299] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0300] ■ R1 is different from R5 and / or R2 is different from R4, and R6 is different from R 10 are the same and R7 is the same as R9;

[0301] or

[0302] ■R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4;

[0303] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0304] This particular embodiment corresponds to the presence of symmetry about axis (I) and axis (III). It also corresponds to the lack of symmetry about axis (II).

[0305] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ic) as defined above as a catalyst for a coupling reaction:

[0306]

[0307] in:

[0308] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0309] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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:

[0310] -R1 is the same as R5,

[0311] -R2 is the same as R4,

[0312] -R6 and R 10 same,

[0313] -R7 is the same as R9;

[0314] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0315] This particular embodiment corresponds to the existence of symmetry with respect to axis (I), axis (II) and axis (III).

[0316] In a particular embodiment, the present invention relates to the use of at least one compound of the following general formula (Ic) as defined above as a catalyst for a coupling reaction:

[0317]

[0318] in:

[0319] ● B, C, D and E are fluorine atoms;

[0320] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0321] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0322] This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl groups carrying the groups B, C, D and E. This has the consequence of modifying the electronic properties of the iron atom of the catalyst.

[0323] In another embodiment, the present invention relates to the use of a compound of formula (I) selected from:

[0324]

[0325] The present invention has as its specific objects the compounds of the following general formula (I):

[0326]

[0327] A is selected from:

[0328] --X group, wherein X is selected from chlorine atom, bromine atom,

[0329] -Group Wherein: M is a coordinating solvent, p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4,

[0330] -Group

[0331] B, C, D and E are identical or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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, at least one of the groups B, C, D or E being different from a hydrogen atom;

[0332] ●When A corresponds to the group hour,

[0333] R1, R5, R6 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 or 2 or 4 to 10 carbon atoms, a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group having 2 to 4 carbon atoms), a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 2 to 20 carbon atoms;

[0334] ●When A corresponds to a -X group or a group hour,

[0335] R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0336] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0337] 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 symmetry or lack of symmetry with respect to axis (I), axis (II) or axis (III).

[0338] The present invention has as its specific objects the compounds of the following general formula (I):

[0339]

[0340] A is selected from:

[0341] --X group, wherein X is selected from chlorine atom, bromine atom,

[0342] -Group Wherein: M is a coordinating solvent, p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4,

[0343] -Group

[0344] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0345] R1, R5, R6 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 2 carbon atoms or 4 to 10 carbon atoms, a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0346] ● R2, R3, R4, R6, R7, R8 and R9 are identical or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0347] ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms;

[0348] Compounds of the following formula are not included:

[0349]

[0350] In this particular embodiment, there may be symmetry or lack of symmetry about axis (I), axis (II) or axis (III).

[0351] The present invention has as its particular objects the compounds of the following general formula (I) as defined above:

[0352]

[0353] in:

[0354] A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, and R 10 and G has the meaning defined above;

[0355] ●B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched alkyl group of 2 to 4 carbon atoms), a straight chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched dialkylamino group of 2 to 20 carbon atoms, and at least one of B, C, D or E is different from the hydrogen atom.

[0356] 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 symmetry or lack of symmetry with respect to axis (I), axis (II) or axis (III).

[0357] The present invention has as its particular objects the compounds of the following general formula (I) as defined above:

[0358]

[0359] in:

[0360] A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, and R 10 and G has the meaning defined above;

[0361] ●B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched alkyl group of 2 to 4 carbon atoms), a straight chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched dialkylamino group of 2 to 20 carbon atoms, and at least one of B, C, D or E is a halogen, especially F.

[0362] In this particular embodiment, at least one of group B, group C, group D and group E is a fluorine atom, and there may be symmetry or lack of symmetry with respect to axis (I), axis (II) or axis (III).

[0363] The present invention has as its particular objects the compounds of the following general formula (I) as defined above:

[0364]

[0365] in

[0366] A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, and R 10 and G has the meaning defined above;

[0367] ●B, C, D and E are fluorine atoms.

[0368] In this particular embodiment, group B, group C, group D and group E are fluorine atoms. This has the consequence of changing the electronic properties of the iron atom of the catalyst and having symmetry with respect to axis (I). Symmetry or lack of symmetry may exist with respect to axis (II) or axis (III).

[0369] The present invention has as its particular objects the compounds of the following general formula (Ia) as defined above:

[0370]

[0371] in:

[0372] ●X is selected from a chlorine atom and a bromine atom;

[0373] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0374] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0375] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0376] The present invention has as its particular objects the compounds of the following general formula (Ia) as defined above:

[0377]

[0378] wherein X and G have the meanings defined above, and

[0379] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0380] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0381] - R1 is different from R5 and / or R2 is different from R4,

[0382] and

[0383] -R6 is different from R 10 And / or R7 is different from R9.

[0384] In this particular embodiment, there is symmetry about axis (I) and a lack of symmetry about axis (II) and axis (III).

[0385] The present invention has as its particular objects the compounds of the following general formula (Ia) as defined above:

[0386]

[0387] wherein X and G have the meanings defined above, and

[0388] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0389] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0390] -R1 is the same as R5,

[0391] -R2 is the same as R4,

[0392] -R6 and R 10 same,

[0393] -R7 is the same as R9.

[0394] In this particular embodiment, there is symmetry about axis (I), axis (II) and axis (III).

[0395] A particular object of the present invention are compounds of the following general formula (Ib) as defined above:

[0396]

[0397] in:

[0398] ●X is selected from a chlorine atom and a bromine atom;

[0399] ●M is the coordinating solvent;

[0400] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0401] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0402] R1, R5, R6 and R10 are identical or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 to 2 carbon atoms or 4 to 10 carbon atoms, a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 1 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9 are identical or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group having 2 to 4 carbon atoms), a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 2 to 20 carbon atoms;

[0403] ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms;

[0404] Compounds of the following formula are not included:

[0405]

[0406] A particular object of the present invention are compounds of the following general formula (Ib) as defined above:

[0407]

[0408] wherein X, M, p and G have the meanings defined above, and

[0409] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0410] R1, R5, R6 and R 10 is selected from the group consisting of: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 to 2 carbon atoms or 4 to 10 carbon atoms, a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9 are selected from the group consisting of: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group having 2 to 4 carbon atoms), a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 2 to 20 carbon atoms, provided that:

[0411] - R1 is different from R5 and / or R2 is different from R4,

[0412] and

[0413] -R6 is different from R 10 And / or R7 is different from R9.

[0414] In this particular embodiment, there is symmetry about axis (I) and a lack of symmetry about axis (II) and axis (III).

[0415] A particular object of the present invention are compounds of the following general formula (Ib) as defined above:

[0416]

[0417] wherein X, M, p and G have the meanings defined above, and

[0418] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0419] R1, R5, R6 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 to 2 or 4 to 10 carbon atoms, a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 2 to 20 carbon atoms, and R2, R3, R4, R6, R7, R8 and R9 are the same and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group having 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group having 2 to 4 carbon atoms), a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group having 2 to 20 carbon atoms, provided that:

[0420] -R1 is the same as R5,

[0421] -R2 is the same as R4,

[0422] -R6 and R 10 same,

[0423] -R7 is the same as R9;

[0424] The following compounds are not included:

[0425]

[0426] In this particular embodiment, there is symmetry about axis (I), axis (II) and axis (III).

[0427] A particular object of the present invention is a compound of the following general formula (Ic):

[0428]

[0429] in:

[0430] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0431] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0432] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0433] A particular object of the present invention are compounds of the following general formula (Ic) as defined above:

[0434]

[0435] in:

[0436] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0437] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0438] -R1 is the same as R5,

[0439] -R2 is the same as R4,

[0440] -R6 and R 10 same,

[0441] -R7 is the same as R9;

[0442] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0443] In this particular embodiment, there is symmetry about axis (I), axis (II) and axis (III).

[0444] A particular object of the present invention are compounds of the following general formula (Ic) as defined above:

[0445]

[0446] in:

[0447] B, C, D and E are selected from: hydrogen atoms, halogens (especially F or Cl), trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms (especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms), straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms, provided that B is identical to E and D is identical to C;

[0448] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms, provided that:

[0449] ■ R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9;

[0450] or

[0451] ■R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4;

[0452] ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

[0453] In this particular embodiment, there is symmetry about axis (I). There is also a lack of symmetry about axis (II) and axis (III).

[0454] The present invention has as its particular objects the compounds as defined above, which are selected from:

[0455]

[0456] In a particular embodiment, the present invention relates to the use of at least one of the compounds of formula (Ia), (Ib) or (Ic) as defined above as a catalyst for carrying out a reaction selected from carbon-carbon bond forming reactions (e.g., Suzuki-Miyaura reaction, Kumada reaction and Sonogashira reaction).

[0457] The term "carbon-carbon bond forming reaction" means that in the result of a reaction, a carbon-carbon bond is formed between two different molecules or within a molecule.

[0458] In another embodiment, a compound of formula (Ia), a compound of formula (Ib) or a compound of formula (Ic) as defined above is used, and the catalytic loading of the compound is 0.01 mol % to 0.1 mol %, 0.1 mol % to 1 mol %, 1 mol % to 10 mol %, 10 mol % to 20 mol %, 20 mol % to 30 mol %, preferably 1 mol % to 10 mol %.

[0459] The term "catalytic loading" refers to the molar equivalent percentage of incorporated catalyst.

[0460] In another embodiment, the invention relates to the use of a compound as defined above for carrying out a Suzuki-Miyaura reaction.

[0461] As a non-limiting example, the Suzuki-Miyaura reaction is carried out in the presence of a halogenated derivative, a boric acid ester and a base (1 / 2 / 1.2 or 2) and a catalyst with stirring at 25°C for 24 hours.

[0462] These compounds used in the Suzuki-Miyaura reaction may be in benzene, toluene, 2-methyltetrahydrofuran, methyl tert-butyl ether, tert-amyl methyl ether or anisole, preferably in benzene.

[0463] These catalysts can be activated during the Suzuki-Miyaura reaction by heating, by microwaves, preferably by heating.

[0464] The reaction medium may be heated to a temperature of 25°C to 150°C, preferably to 25°C.

[0465] The use of these catalysts in the Suzuki-Miyaura reaction can be carried out in a batch mode or a continuous flow mode, preferably in a batch mode.

[0466] In another embodiment, the invention relates to the use of a compound as defined above, wherein the implementation of Suzuki-Miyaura comprises the use of a base selected from LiNMeEt, LiNMe2, LiNEt2, LiNiPr2, LiNTMS2, LiNPhMe, in particular LiNMeEt and LiNMe2.

[0467] In another embodiment, the invention relates to the use as defined above for the synthesis of one of the compounds of the following formulae:

[0468]

[0469]

[0470]

[0471] Wherein Y is selected from:

[0472] ■Hydrogen atoms,

[0473] ■ a straight-chain or branched alkyl group of 1 to 10 carbon atoms,

[0474] ■ a straight-chain or branched alkoxy group of 1 to 10 carbon atoms,

[0475] ■-OPh group,

[0476] ■ an alkylamino group or a dialkylamino group substituted by one or two straight-chain alkyl groups of 1 to 10 carbon atoms,

[0477] ■ halogen, in particular fluorine, chlorine or bromine,

[0478] ■Nitro NO2 group,

[0479] ■Trifluoromethyl group CF3,

[0480] ■Group

[0481] The present invention has as its particular objects novel compounds of the formula:

[0482]

[0483] The present invention has as its particular objects novel compounds of the formula:

[0484]

[0485] The present invention has as its particular objects novel compounds of the formula:

[0486]

[0487] The present invention has as its particular objects novel compounds of the formula:

[0488]

[0489] The present invention has as its particular objects novel compounds of the formula:

[0490]

[0491] The present invention has as its particular objects novel compounds of the formula:

[0492]

[0493] In another embodiment, the invention relates to the use of a compound of formula (Ia), a compound of formula (Ib) or a compound of formula (Ic) as defined above for carrying out a Suzuki-Miyaura reaction of a compound of formula (S1) with a compound Z-Hal of formula (S2),

[0494]

[0495] Wherein W is selected from:

[0496] -Phenyl wherein Y is selected from the group consisting of: a hydrogen atom, a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, an -OPh group, an alkylamino group or a dialkylamino group substituted by one or two straight-chain alkyl groups having 1 to 10 carbon atoms, a halogen (especially a fluorine atom, a chlorine atom or a bromine atom), a nitro NO2 group, a trifluoromethyl group CF3, a group

[0497] -2-Thienyl group

[0498] -3-Furanyl group

[0499] -2-Naphthyl group

[0500] -6-Quinolyl group

[0501] -Group

[0502] -Group

[0503] -Group

[0504] -Group

[0505] -Group

[0506] -Group

[0507] - a linear or branched alkyl group of 1 to 20 carbon atoms or a cyclic group of 3 to 12 carbon atoms (especially an octyl group),

[0508] -Group

[0509] And V is selected from:

[0510] -Group Where q is equal to 0 or 1,

[0511] -Group

[0512] In the compound Z-Hal of formula (S2),

[0513] Z is selected from:

[0514] - a straight-chain or branched alkyl group having 1 to 20 carbon atoms or a cyclic group having 3 to 12 carbon atoms (especially an octyl group, a hexyl group, a cycloheptyl group, a cyclopentyl group or a cyclopropyl group),

[0515] -With style 1-adamantyl group,

[0516] -With style The benzyl group,

[0517] -Group

[0518] -Group

[0519] -Group

[0520] -Group

[0521] -Group

[0522] -Group

[0523] -Group

[0524] -Group

[0525] And Hal is selected from:

[0526] - chlorine atoms,

[0527] - bromine atoms,

[0528] -Iodine atom.

[0529] In one embodiment, the invention relates to a process for preparing a compound of formula (Ia) as defined above:

[0530]

[0531] in:

[0532] ●X is selected from a chlorine atom and a bromine atom;

[0533] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0534] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0535] ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms;

[0536] The method comprises the steps of sequentially adding n-butyl lithium and iron (II) halide FeX2 to a compound of formula (II),

[0537]

[0538] Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10and G has the meaning defined above.

[0539] In this embodiment, the addition reaction here involves the deprotonation of the secondary amine function located between the two phenyl groups of compound (II) to form an N—Fe bond. 10 However, due to the steric hindrance around the iron atom, lithium does not coordinate with compound (Ia). The obtained compound (Ia) is sensitive to oxygen and must be stored under inert atmosphere.

[0540] In another embodiment, the present invention relates to a preparation method as defined above, wherein the above-mentioned adding step is carried out in a cyclic ether solvent or a non-cyclic ether solvent (in particular, selected from tetrahydrofuran, ethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran) under stirring from -78°C to 25°C (preferably at -78°C) for 30 minutes, then at 25°C for 2 hours, and then for 15 hours.

[0541] The term "ether solvent" refers to a solvent in which at least one ether functional group is present.

[0542] This sequential addition can be done in a single solvent, or by adding n-butyllithium in a first solvent and then, after evaporation of that solvent, adding FeX2 in a second solvent.

[0543] As a non-limiting example, this step of sequentially adding n-butyllithium and FeX2 (1:1) can be carried out as follows: n-butyllithium is added in hexane, and then FeX2 is added in a cyclic ether solvent or a non-cyclic ether solvent (particularly, selected from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole).

[0544] As a non-limiting example, this step of sequentially adding n-butyllithium and FeX2 (1:1) can be carried out as follows: n-butyllithium is added in a non-coordinating non-polar solvent (particularly, selected from benzene, hexane, toluene, cyclohexane, methylcyclohexane), followed by FeX2 in tetrahydrofuran.

[0545] A "non-coordinating non-polar solvent" is a solvent in which the center of gravity of the sum of the difference in electronegativity is confounded.

[0546] As a non-limiting example, this step of adding n-butyllithium and ferrous chloride (1 / 1) can be carried out under stirring in tetrahydrofuran at a temperature of -78°C to 25°C (preferably -78°C to -30°C) for 30 minutes, then from -78°C to 25°C (preferably from 0°C to 25°C) for 2 hours, and then from -78°C to 25°C (preferably from 0°C to 25°C) for 15 hours.

[0547] In another embodiment, the present invention relates to a preparation process as defined above, said process comprising the step of preparing a compound of formula (II):

[0548]

[0549] Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 Having the meaning defined above, the step comprises an aromatic nucleophilic substitution step of a compound of formula (III) on a compound of formula (IV) to obtain the compound of formula (II):

[0550]

[0551] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom,

[0552] Compound of formula (IV):

[0553]

[0554] Among them, R6, R7, R8, R9 and R 10 has the meaning defined above,

[0555] The following compounds are not included:

[0556]

[0557] In this embodiment, aromatic nucleophilic substitution occurs by the lithium amide of compound (IV) replacing the fluorine of compound (III).

[0558] In another embodiment, the present invention relates to a preparation process as defined above, wherein the above-mentioned aromatic nucleophilic substitution step is carried out in a cyclic ether solvent or a non-cyclic ether solvent (in particular, selected from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran) and at a temperature of 25°C to 125°C (preferably 25°C).

[0559] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at a temperature of 25°C to 125°C (preferably 25°C to 75°C).

[0560] In another embodiment, the present invention relates to the preparation process as defined above, wherein the above-mentioned aromatic nucleophilic substitution step is carried out in a non-coordinating non-polar solvent (in particular, selected from benzene, hexane, toluene, cyclohexane, methylcyclohexane, preferably toluene) and at a temperature of 25°C to 125°C (preferably 25°C or 90°C).

[0561] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at a temperature of 25°C to 125°C (preferably 25°C to 75°C).

[0562] In another embodiment, the present invention relates to a preparation process as defined above, said process comprising the step of preparing a compound of formula (III):

[0563]

[0564] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom,

[0565] The step comprises a condensation reaction of a compound of formula (V) on a compound of formula (VI) to obtain the compound of formula (III):

[0566]

[0567] wherein B, C, D and E have the meanings defined above, and F is a fluorine atom,

[0568] Compounds of formula (VI):

[0569]

[0570] wherein R1, R2, R3, R4 and R5 have the meanings defined above,

[0571] Compounds of the following formula are not included:

[0572]

[0573] In this embodiment, the condensation step to form compound (III) is carried out from an aldehyde, compound (V), and an amine, compound (IV).

[0574] In another embodiment, the present invention relates to a preparation process as defined above, wherein the above-mentioned condensation step is carried out at a temperature of 0°C to 150°C in a non-coordinating solvent or an alcohol non-polar 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 in hexane at 25°C, or preferably in toluene at 150°C, or preferably in ethanol at 90°C.

[0575] The term "alcohol solvent" refers to a solvent containing hydroxyl functional groups.

[0576] As a non-limiting example, this condensation of an aldehyde and an amine (1:1) is carried out in the presence of MgSO4 (0.08 mol%) in hexane at a temperature between 25°C and 75°C (preferably 25°C).

[0577] As a non-limiting example, this condensation of aldehydes and amines is carried out in the presence of p-toluenesulfonic acid (1 / 1.1 / 0.01) in toluene at a temperature ranging from 25°C to 150°C, preferably 150°C.

[0578] As a non-limiting example, this condensation of aldehyde and amine (1:1.1) is carried out in ethanol at a temperature between 25°C and 90°C, preferably 25°C.

[0579] In another embodiment, the present invention relates to a process for preparing a compound of formula (Ia) as defined above:

[0580]

[0581] in:

[0582] ●X is selected from a chlorine atom and a bromine atom;

[0583] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0584] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 2 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0585] ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms;

[0586] The method comprises: a) a condensation step of a compound of formula (V) on a compound of formula (VI) to obtain a compound of formula (III),

[0587]

[0588] wherein B, C, D and E have the meanings defined above and F is a fluorine atom,

[0589] Compound of formula (VI):

[0590]

[0591] wherein R1, R2, R3, R4 and R5 have the meanings defined above,

[0592]

[0593] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom,

[0594] b) an aromatic nucleophilic substitution step of the compound of formula (III) on the compound of formula (IV) to obtain a compound of formula (II):

[0595]

[0596] Among them, R6, R7, R8, R9 and R 10 has the meaning defined above,

[0597]

[0598] Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 has the meaning defined above,

[0599] c) sequentially adding n-butyllithium and iron (II) halide FeX2 to the compound of formula (II) to obtain the compound of formula (Ia).

[0600] In another embodiment, the present invention relates to a process for preparing a compound of formula (Ib) as defined above:

[0601]

[0602] in:

[0603] ●X is selected from a chlorine atom and a bromine atom;

[0604] ●M is the coordinating solvent;

[0605] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0606] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0607] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 1 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0608] ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms;

[0609] The method comprises the steps of sequentially adding n-butyl lithium and iron (II) halide FeX2 to a compound of formula (II):

[0610]

[0611] Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 and G has the meaning defined above.

[0612] In this embodiment, the addition reaction here involves the deprotonation of the secondary amine functional group between the two phenyl groups of compound (II) to form an N-Fe bond. The first X atom bonded to iron coordinates to a lithium atom, which in turn is already coordinated to another X atom. This coordination can be due to B, C, D, E, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 The resulting compound is sensitive to ambient air and must be stored under inert atmosphere.

[0613] In another embodiment, the present invention relates to a preparation method as defined above, wherein the above-mentioned adding step is carried out in a cyclic ether solvent or a non-cyclic ether solvent (in particular, selected from tetrahydrofuran, ethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran) under stirring from -78°C to 25°C (preferably at -78°C) for 30 minutes, then at 25°C for 2 hours, and then at 25°C for 15 hours.

[0614] This sequential addition can be carried out in a single solvent, or by adding n-butyllithium in a first solvent and then, after evaporation of this solvent, adding FeX2 in a second solvent.

[0615] As a non-limiting example, this sequential addition step of n-butyllithium and FeX2 (1:1) can be carried out as follows: n-butyllithium is added in hexane, and then FeX2 is added in a cyclic ether solvent or a non-cyclic ether solvent (particularly, selected from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole).

[0616] As a non-limiting example, this sequential addition step of n-butyllithium and FeX2 (1:1) can be carried out as follows: n-butyllithium is added in a non-coordinating non-polar solvent (particularly, selected from benzene, hexane, toluene, cyclohexane, methylcyclohexane), followed by FeX2 in tetrahydrofuran.

[0617] As a non-limiting example, this addition step of n-butyllithium and FeCl2 (1 / 1) can be carried out in tetrahydrofuran under stirring at a temperature of -78°C to 25°C (preferably -78°C to -30°C) for 30 minutes, then from -78°C to 25°C (preferably from 0°C to 25°C) for 2 hours, and then from -78°C to 25°C (preferably from 0°C to 25°C) for 15 hours.

[0618] In another embodiment, the present invention relates to a preparation process as defined above, said process comprising the step of preparing a compound of formula (II):

[0619]

[0620] Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 has the meaning defined above, said step comprising an aromatic nucleophilic substitution step of a compound of formula (III) on a compound of formula (IV) to obtain said compound of formula (II),

[0621]

[0622] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom,

[0623] Compound of formula (IV):

[0624]

[0625] Among them, R6, R7, R8, R9 and R 10 has the meaning defined above,

[0626] The following compounds are not included:

[0627]

[0628]

[0629] In this embodiment, aromatic nucleophilic substitution occurs by the lithium amide of compound (IV) replacing the fluorine of compound (III).

[0630] In another embodiment, the present invention relates to a preparation process as defined above, wherein the above-mentioned aromatic nucleophilic substitution step is carried out in a cyclic ether solvent or a non-cyclic ether solvent (in particular, selected from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran) and at a temperature of 25°C to 125°C (preferably 25°C).

[0631] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at a temperature of 25°C to 125°C (preferably 25°C to 75°C).

[0632] In another embodiment, the present invention relates to the preparation process as defined above, wherein the above-mentioned aromatic nucleophilic substitution step is carried out in a non-coordinating non-polar solvent (in particular, selected from benzene, hexane, toluene, cyclohexane, methylcyclohexane, preferably toluene) and at a temperature of 25°C to 125°C (preferably 25°C or 90°C).

[0633] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at a temperature of 25°C to 125°C (preferably 25°C to 75°C).

[0634] In another embodiment, the present invention relates to a preparation process as defined above, comprising the step of preparing a compound of formula (III):

[0635]

[0636] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom,

[0637] The step comprises a condensation reaction of a compound of formula (V) on a compound of formula (VI) to obtain the compound of formula (III),

[0638]

[0639] wherein B, C, D and E have the meanings defined above, and F is a fluorine atom,

[0640] Compound of formula (VI):

[0641]

[0642] wherein R1, R2, R3, R4 and R5 have the meanings defined above,

[0643] Compounds of the following formula are not included:

[0644]

[0645] In this embodiment, the condensation step to form the imine of compound (III) is carried out from an aldehyde, compound (V), and an amine, compound (IV).

[0646] In another embodiment, the present invention relates to a preparation process as defined above, wherein the above-mentioned condensation step is carried out in a non-coordinating solvent or an alcohol non-polar 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) at a temperature of 0°C to 150°C, preferably in hexane at 25°C, or preferably in toluene at 150°C, or preferably in ethanol at 90°C.

[0647] As a non-limiting example, this condensation of an aldehyde and an amine (1:1) is carried out in the presence of MgSO4 (0.08 mol%) in hexane at a temperature of 25°C to 75°C (preferably 25°C).

[0648] As a non-limiting example, this condensation of aldehydes and amines is carried out in the presence of p-toluenesulfonic acid (1 / 1.1 / 0.01) in toluene at a temperature ranging from 25°C to 150°C, preferably 150°C.

[0649] As a non-limiting example, this condensation of aldehyde and amine (1 / 1.1) is carried out in ethanol at a temperature between 25°C and 90°C, preferably 25°C.

[0650] In another embodiment, the present invention relates to a process for preparing a compound of formula (Ib) as defined above:

[0651]

[0652] in:

[0653] ●X is selected from a chlorine atom and a bromine atom;

[0654] ●M is the coordinating solvent;

[0655] ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4;

[0656] ● B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched alkyl group of 2 to 4 carbon atoms), a straight chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched dialkylamino group of 2 to 10 carbon atoms;

[0657] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 1 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0658] ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms;

[0659] The method comprises: a) a condensation step of a compound of formula (V) on a compound of formula (VI) to obtain a compound of formula (III),

[0660]

[0661] wherein B, C, D and E have the meanings defined above and F is a fluorine atom,

[0662] Compound of formula (VI):

[0663]

[0664] wherein R1, R2, R3, R4 and R5 have the meanings defined above,

[0665]

[0666] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom;

[0667] b) an aromatic nucleophilic substitution step of the compound of formula (III) on the compound of formula (IV) to obtain a compound of formula (II):

[0668]

[0669] Among them, R6, R7, R8, R9 and R 10 has the meaning defined above,

[0670]

[0671] Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 has the meaning defined above;

[0672] c) a step of sequentially adding n-butyllithium and iron (II) halide FeX2 to the compound of formula (II) to obtain a compound of formula (Ib).

[0673] In a particular embodiment, the invention relates to a process for the preparation of a compound of formula (Ic) as defined above:

[0674]

[0675] in:

[0676] B, C, D and E are identical or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms (especially 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;

[0677] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 1 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0678] ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms;

[0679] The method comprises the steps of sequentially adding n-butyl lithium and iron (III) triacetylacetonate to the compound of formula (II) to obtain the compound of formula (Ic).

[0680]

[0681] Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 has the meaning defined above.

[0682] In this embodiment, the addition reaction here involves the deprotonation of the secondary amine function located between the two phenyl groups of compound (II) to form an N—Fe bond. The compound of formula (Ic) thus obtained is stable in ambient air.

[0683] In another embodiment, the present invention relates to a preparation process as defined above, wherein the above-mentioned adding step is carried out under stirring in a cyclic ether solvent or a non-cyclic ether solvent (in particular, selected from tetrahydrofuran, ethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran) from -78°C to 25°C (preferably at 25°C), and then at 25°C for 16 hours.

[0684] This sequential addition can be done in a single solvent, or by adding n-butyllithium in a first solvent and then, after evaporation of this solvent, adding Fe(acac)3 in a second solvent.

[0685] As a non-limiting example, this sequential addition step of n-butyllithium and Fe(acac)3(1 / 1) can be carried out as follows: n-butyllithium is added in hexane, and then Fe(acac)3 is added in a cyclic ether solvent or a non-cyclic ether solvent (particularly, selected from tetrahydrofuran, ethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole).

[0686] As a non-limiting example, this sequential addition step of n-butyllithium and Fe(acac)3(1 / 1) can be carried out as follows: n-butyllithium is added in a non-coordinating non-polar solvent (particularly, selected from benzene, hexane, toluene, cyclohexane, methylcyclohexane), and then Fe(acac)3 is added in tetrahydrofuran.

[0687] As a non-limiting example, this addition step of n-butyllithium and Fe(acac)3(1 / 1) can be carried out in tetrahydrofuran at a temperature of -78°C to 25°C (preferably -78°C to -30°C) for 30 minutes, then from -78°C to 25°C (preferably from 0°C to 25°C) for 2 hours, and then from -78°C to 25°C (preferably at 25°C) for 16 hours.

[0688] In another embodiment, the present invention relates to a preparation process as defined above, said process comprising the step of preparing a compound of formula (II):

[0689]

[0690] Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 has the meaning defined above, said step comprising an aromatic nucleophilic substitution step of a compound of formula (III) on a compound of formula (IV) to obtain said compound of formula (II),

[0691]

[0692] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom,

[0693] Compound of formula (IV):

[0694]

[0695] Among them, R6, R7, R8, R9 and R 10 has the meaning defined above.

[0696] In this embodiment, aromatic nucleophilic substitution occurs by the lithium amide of compound (IV) replacing the fluorine of compound (III).

[0697] In another embodiment, the present invention relates to the preparation process as defined above, wherein the above-mentioned aromatic substitution step is carried out in a cyclic ether solvent or a non-cyclic ether solvent (in particular, selected from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butyl methyl ether, tert-butyl ethyl ether, methyltetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran) and at a temperature of 25°C to 125°C (preferably 25°C).

[0698] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at a temperature of 25°C to 125°C (preferably 25°C to 75°C).

[0699] In another embodiment, the present invention relates to the preparation process as defined above, wherein the above-mentioned adding step is carried out in a non-coordinating non-polar solvent (in particular, selected from benzene, hexane, toluene, cyclohexane, methylcyclohexane, preferably toluene) and at a temperature of 25°C to 125°C (preferably 25°C or 90°C).

[0700] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at a temperature of 25° C. to 125° C. (preferably 90° C. to 125° C.). As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at a temperature of 25° C. to 125° C. (preferably 25° C. to 75° C.).

[0701] In another embodiment, the present invention relates to a preparation process as defined above, said process comprising the step of preparing a compound of formula (III):

[0702]

[0703] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom,

[0704] The step comprises a condensation step of the compound of formula (V) on the compound of formula (VI) to obtain the compound of formula (III),

[0705]

[0706] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom,

[0707] Compounds of formula (VI):

[0708]

[0709] wherein R1, R2, R3, R4 and R5 have the meanings defined above.

[0710] In this embodiment, the imine formation step of compound (III) is carried out from an aldehyde, compound (V), and an amine, compound (IV).

[0711] In another embodiment, the present invention relates to a preparation process as defined above, wherein the above-mentioned condensation step is carried out at a temperature of 0°C to 150°C in a non-coordinating non-polar solvent or an alcohol solvent (in particular, selected from hexane, toluene, benzene, cyclohexane, methylcyclohexane, 1-butanol, 2-butanol, isobutanol, tert-butanol, 2-propanol, isopropanol, methanol, or ethanol), preferably at 25°C in hexane, or preferably at 150°C in toluene, or preferably at 90°C in ethanol.

[0712] As a non-limiting example, this condensation of an aldehyde and an amine (1:1) is carried out in the presence of MgSO4 (0.08 mol%) in hexane at a temperature of 25°C to 75°C (preferably 25°C).

[0713] As a non-limiting example, this condensation of aldehydes and amines is carried out in the presence of p-toluenesulfonic acid (1 / 1.1 / 0.01) in toluene at a temperature ranging from 25°C to 150°C, preferably 150°C.

[0714] As a non-limiting example, this condensation of aldehyde and amine (1 / 1.1) is carried out in ethanol at a temperature between 25°C and 90°C, preferably 25°C.

[0715] In another embodiment, the invention relates to a process for the preparation of a compound of formula (Ic) as defined above,

[0716]

[0717] in:

[0718] B, C, D and E are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight chain or branched chain alkyl group of 1 to 10 carbon atoms (especially a straight chain or branched chain alkyl group of 2 to 4 carbon atoms), a straight chain or branched chain alkoxy group of 1 to 10 carbon atoms, or a straight chain or branched chain dialkylamino group of 2 to 20 carbon atoms;

[0719] ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are selected from: a hydrogen atom, a halogen (especially F or Cl), a trifluoromethyl group CF3, a straight-chain or branched alkyl group of 1 to 10 carbon atoms (especially a straight-chain or branched alkyl group of 1 to 4 carbon atoms), a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, or a straight-chain or branched dialkylamino group of 2 to 20 carbon atoms;

[0720] ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms;

[0721] The method comprises: a) a condensation step of a compound of formula (V) on a compound of formula (VI) to obtain a compound of formula (III),

[0722]

[0723] wherein B, C, D and E have the meanings defined above, and F is a fluorine atom,

[0724] Compound of formula (VI):

[0725]

[0726] wherein R1, R2, R3, R4 and R5 have the meanings defined above,

[0727]

[0728] wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom;

[0729] b) an aromatic nucleophilic substitution step of the compound of formula (III) on the compound of formula (IV) to obtain a compound of formula (II):

[0730]

[0731] Among them, R6, R7, R8, R9 and R 10 has the meaning defined above,

[0732]

[0733] Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 has the meaning defined above;

[0734] (c) a step of sequentially adding n-butyllithium and iron (III) triacetylacetonate to the compound of formula (II) to obtain the compound of formula (Ic). Example

[0735] Materials and methods

[0736] 1 H and 13 C NMR spectra were obtained at 298 K on a Bruker AM250, AV300 or AV360 MHz Bruker spectrometer. 7 Li and 19 The NMR spectra of F were obtained at 295 K on Bruker 300 and 250 spectrometers, respectively.1 The chemical shifts of the H spectra were measured using an internal reference, which was either protonated CHCl3 residual in CDCl3 (7.24 ppm) or protonated benzene residual in benzene-d6 (7.16 ppm).

[0737] Elemental analyses were performed at Analytische Laboratorien GMBH, Lindlar, Germany.

[0738] High resolution mass spectra were measured by electrospray ionization (ESI) with a Bruker MicrOTOFq time-of-flight mass spectrometer or a LCT Waters mass spectrometer using electrospray ionization time-of-flight mass spectrometry (ESI-TOF).

[0739] The following are general procedures for preparing compounds of formula (Ia), compounds of formula (II), and compounds of formula (III).

[0740]

[0741] wherein the radicals R2, R4, R7 and R9 represent hydrogen atoms, and the radicals R1, R3, R5, R6, R8 and R 10 Have the meanings shown in the following table [Table 1].

[0742]

[0743] [a] Program A1 [b] Program A2 [c] Program A3 [d] Program B1 [e] Program B2, 90°C [f] Program B2, 25°C [g] Program B3 [h] Program C1

[0744] Procedure A1: To a solution of the appropriate 2-fluorobenzaldehyde derivative (1 eq) and MgSO4 in hexane (c = 1.6 M) was added the appropriate aniline derivative (1 eq) with stirring at 25° C. The solution was stirred at this temperature for 2 hours, then filtered, concentrated under reduced pressure and cooled to -20° C. to give the corresponding compound (III) in the form of yellow crystals.

[0745] Procedure A2: In a Dean-Stark apparatus, p-toluenesulfonic acid (0.01 eq) was added to a solution of the appropriate 2-fluorobenzaldehyde derivative (1 eq) and the appropriate aniline derivative (1.1 eq) in toluene (c = 0.40 M) under stirring. The solution was heated to 150°C for 15 hours. The solution was then cooled to 25°C and a saturated aqueous Na2CO3 solution was added. The aqueous phase was separated and extracted with Et2O. The organic phases were combined, dried over MgSO4, filtered and concentrated under reduced pressure to give a pale yellow oil. Recrystallization in hexane at -20°C gave the corresponding compound (III) in the form of yellow crystals.

[0746] Procedure A3: To a solution of perfluorobenzaldehyde (1 eq) in EtOH (c = 1.5 M) was added 2,6-diisopropylamine (1.1 eq) at 25°C, and the solution was stirred at this temperature for 2 hours. The solution was concentrated under reduced pressure and then cooled to -20°C to give the corresponding compound (III) in the form of yellow crystals.

[0747] Procedure B1: To a solution of the appropriate aniline derivative (1 eq) in tetrahydrofuran (THF) (c=1 M) is added a solution of n-butyllithium (n-BuLi) (1 eq) with stirring at -78°C. The solution is stirred for 15 hours and then cannulated to a solution of the appropriate compound (III) (1 eq) in THF (c=1 M) at 25°C. The solution is stirred for 2 hours at this temperature and then water is added. The aqueous phase is separated and extracted with hexane. The organic phases are combined, dried over MgSO4, filtered and concentrated under reduced pressure to give a brown oil. Recrystallization from hot ethanol at -20°C gives the corresponding compound (II) in the form of yellow crystals.

[0748] Procedure B2: To a suspension of lithium (2,6-diisopropylphenyl)amide (2.5 eq) in toluene (10 mL) at 25°C was added the appropriate compound (III) (1 eq). The solution was heated to 90°C with stirring for 72 hours, or to 25°C for 48 hours. The solution was then cooled to 25°C and a saturated aqueous solution of Na2CO3 was added. The aqueous phase was separated and extracted with Et2O. The organic phases were combined, dried over MgSO4, filtered and concentrated under reduced pressure to give a light brown oil. Recrystallization in hot ethanol gave the corresponding compound (II) in the form of pale yellow crystals.

[0749] Procedure B3: TiCl4 (0.5 eq) was added to a solution of 2,6-diisopropylaniline (3 eq) in hexane (c = 1 M) at 0°C with stirring. The solution was stirred at 25°C for 24 hours. The solution was then heated to reflux and a solution of 2-fluoroacetophenone (1 eq) in hexane (c = 2.6 M) was added. The solution was heated to reflux for 16 hours. A brown solid appeared in the solution. The solution was filtered and the solid was washed with hexane. The organic phase was collected and washed with water. The aqueous phase was separated and then extracted with hexane. The organic phase was collected and dried over MgSO4, 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 hours and then the solution was placed into a solution of the previously synthesized yellow oil in THF at 25°C with a cannula. The solution was stirred at 25°C for 2 hours. Water was then added to the medium. The aqueous phase was separated and then extracted with Et2O. The organic phase was collected, dried over MgSO4, filtered and the solvent evaporated under vacuum to give a light brown oil. The light brown oil was recrystallized in hot ethanol to give the corresponding compound (II) in the form of a pale white powder.

[0750] Procedure C1: To a solution of the appropriate compound (III) (1 eq) in THF (c=0.4 M) was added N-BuLi (1.6 eq) with stirring at -78°C. The cooling bath was removed 30 minutes after the addition. The solution was stirred at 25°C for 2 hours. FeCl2 (1 eq) was then added. The solution was stirred at 25°C for 15 hours and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane and then extracted with Et2O. The dark red solution was concentrated and cooled to -20°C to give the corresponding compound (Ia) as a dark red powder.

[0751] Example 1 :Synthesis of (E)-N-mesityl-1-(perfluorophenyl)methanimine

[0752]

[0753] To a solution of perfluorobenzaldehyde (1.8 mL, 15 mmol) in EtOH (10 mL) was added 2,4,6-trimethylaniline (2.3 mL, 16.05 mmol) at 25° C., and the solution was refluxed (90° C.) for 16 h. After evaporation of the solvent and recrystallization from Et2O at −20° C., (E)-N-mesityl-1-(perfluorophenyl)methanimine (4.4 g, 14 mmol, 94%) was obtained in the form of yellow crystals.

[0754]

[0755] Example 2: Synthesis of (E)-N-(2-ethylphenyl)-1-(pentafluorophenyl)methanimine

[0756]

[0757] To a solution of perfluorobenzaldehyde (1.8 mL, 15 mmol) in EtOH (10 mL) was added 2-ethylaniline (2.0 mL, 16.5 mmol) at 25° C., and the solution was refluxed (90° C.) for 16 h. After evaporation of the solvent and recrystallization from diethyl ether at −20° C., (E)-N-(2-ethylphenyl)-1-(pentafluorophenyl)methanimine (3.7 g, 13.3 mmol, 82%) was obtained in the form of yellow crystals.

[0758]

[0759] Example 3: (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesityl imino)methyl)aniline Synthesis

[0760]

[0761] (E)-N-trimethylphenyl-1-(perfluorophenyl) azomethine (2.5 g, 8 mmol) was added to a solution of (2,4,6-trimethylphenyl) lithium amide (2.8 g, 20 mmol) in toluene (16 mL), and then stirred at 25 ° C for 48 hours. After adding saturated NaHCO solution (50 mL), the aqueous phase was extracted with EtOAc (50 mL). The organic phase was collected, dried over MgSO, filtered and concentrated under reduced pressure. Recrystallization was carried out in MeOH at -20 ° C, and the product (E)-2,3,4,5-tetrafluoro-N-trimethylphenyl-6-((trimethylphenyl imino) methyl) aniline was obtained as pale yellow crystals (3.3 g, 7.7 mmol, 96%).

[0762]

[0763] Example 4: (E)-N-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3,4,5,6-tetrafluoro Synthesis of Aniline

[0764]

[0765] To a solution of 2-(ethylphenyl)lithium amide (2.5 mL, 20 mmol) in toluene (16 mL) was added (E)-N-(2-ethylphenyl)-1-(pentafluorophenyl)methanimine (2.4 g, 8 mmol), followed by stirring at 25 °C for 48 hours. After addition of saturated NaHCO solution (50 mL), the aqueous phase was extracted with EtOAc (50 mL). The organic phase was collected, dried over MgSO, filtered and concentrated under reduced pressure. Recrystallization was carried out in MeOH at -20 °C to give the product (E)-N-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3,4,5,6-tetrafluoroaniline as pale yellow crystals (2.7 g, 6.75 mmol, 84%).

[0766]

[0767] Example 5: Synthesis of P5

[0768]

[0769] To a solution of (E)-2,3,4,5-tetrafluoro-N-trimethylol-6-((trimethylolimino)methyl)aniline (2.1 g, 5 mmol) in THF (10 mL) at -78°C was added n-BuLi (2.5 M in hexanes) (2 mL, 5 mmol) with stirring. The cooling bath was removed 30 minutes after the addition. The solution was stirred at 25°C for 4 hours. FeCl2 (0.63 g, 5 mmol) was then added. The solution was stirred overnight and the solvent was then evaporated under reduced pressure. The residual solid was washed with hexanes or pentane (10 mL) and extracted with Et2O (25 mL). The ether solution was filtered, then concentrated and replaced with hexanes (20 mL). After adding a few drops of THF and cooling to -20°C, red crystals of P5 product (2.09 g, 3.0 mmol, 60%) were obtained.

[0770]

[0771] Example 6: Synthesis of P6

[0772]

[0773] 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 was added n-BuLi (2.5 M in hexanes) (2 mL, 5 mmol) with stirring. The cooling bath was removed 30 minutes after the addition. The solution was stirred at 25°C for 4 hours. FeCl2 (0.63 g, 5 mmol) was then added. The solution was stirred overnight and the solvent was then evaporated under reduced pressure. The residual solid was washed with hexanes or pentane (10 mL) and extracted with Et2O (25 mL). The ether solution was filtered, then concentrated and replaced with hexanes (20 mL). After adding a few drops of THF and cooling to -20°C, red crystals of P6 product (1.1 g, 1.6 mmol, 35%) were obtained.

[0774]

[0775] Example 7: Synthesis of P7

[0776]

[0777] To a solution of (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesityl imino)methyl)aniline (3 g, 7 mmol) in THF (15 mL) at -78°C was added n-BuLi (2.5 M in hexanes) (2.8 mL, 7 mmol) with stirring. The cooling bath was removed 30 minutes after the addition. The solution was stirred at 25°C for 4 hours and concentrated under reduced pressure to give (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesityl imino)methyl)aniline lithium amide. At 25°C, to a solution of Fe(acac)3 (2.1 g, 6 mmol) in THF (12 ml) was added (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesityl imino)methyl)aniline lithium amide (2.6 g, 6 mmol) in THF (6 ml) under stirring, and the solution was then stirred at the same temperature for 16 hours. The red solution turned dark green. After cooling to -20°C, filtration and evaporation were performed on celite, and the solid was washed with cold pentane to obtain a dark green powder of the P7 product (2 g, 2.9 mmol, 50%).

[0778]

[0779] Example 8: Synthesis of P8

[0780]

[0781] 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 was added n-BuLi (2.5 M in hexanes) (0.8 mL, 2.0 mmol) with stirring. The cooling bath was removed 30 minutes after the addition. The solution was stirred at 25°C for 4 hours. FeBr2 (0.389 g, 1.8 mmol) was then added. The solution was stirred overnight and the solvent was then evaporated under reduced pressure. The residual solid was washed with hexanes or pentane and extracted with Et2O. The ether solution was filtered, then concentrated and replaced with hexanes. After adding a few drops of THF and cooling to -20°C, red crystals of P8 product (0.63 g, 0.8 mmol, 44%) were obtained.

[0782]

[0783] Example 9: Byers Synthesis of Phenylcycloheptane (Reference Example)

[0784]

[0785] The reaction was carried out in an inert atmosphere in a glove box. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c=0.5 M) was added to EtNMeLi (1.2 eq) and Byers catalyst (Angew. Chem., Int. Ed. 2020, 59, 5392) (10 mol%).

[0786]

[0787] A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) was added to the solution, and then supplemented by adding benzene to obtain a total concentration of 0.08 M bromocycloheptane. The reaction mixture was stirred at 25 ° C for 5 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Phenylcycloheptane was obtained in a yield of 94% using dodecane as an internal standard through gas chromatography.

[0788] Example 10: Synthesis of Phenylcycloheptane A

[0789]

[0790] The reaction is carried out in a glove box in an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) is added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution, and then supplemented by adding benzene to obtain a total concentration of 0.08 M bromocycloheptane. The reaction mixture is stirred at 25 ° C for 4 hours, and then a saturated NH4Cl aqueous solution is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Phenylcycloheptane is obtained with a yield of> 99% by gas chromatography using dodecane as an internal standard. Silica gel column chromatography is performed to obtain phenylcycloheptane with a yield of 95%.

[0791]

[0792] This yield is higher than that obtained with Byers catalyst and the reaction is faster.

[0793] Example 11: Synthesis of Phenylcycloheptane B

[0794]

[0795] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P6 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of bromocycloheptane of 0.08 M. The reaction mixture was stirred at 25 ° C for 24 hours (non-optimized time), 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. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis gave phenylcycloheptane in >99% yield.

[0796] Example 12: Synthesis of Phenylcycloheptane C

[0797]

[0798] The reaction was carried out in a glove box under an inert atmosphere. The P7 catalyst was previously exposed to ambient air for 2 weeks. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to the P7 catalyst (10 mol %) and EtNMeLi (2.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of bromocycloheptane of 0.08 M. The reaction mixture was stirred at 25 °C for 24 h (non-optimized reaction time), and then saturated aqueous NH4Cl solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis revealed that phenylcycloheptane was obtained in 89% yield.

[0799] Example 13: Synthesis of Phenylcycloheptane D

[0800]

[0801] The reaction was carried out outside the glove box in an inert atmosphere. The P7 catalyst was previously exposed to ambient air for 2 weeks. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to the P7 catalyst (10 mol%) and EtNMeLi (2.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of bromocycloheptane of 0.08 M. The reaction mixture was stirred at 25 °C for 24 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. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis revealed that phenylcycloheptane was obtained in 87% yield.

[0802] This example shows that the catalyst is not sensitive to ambient air, since even after being exposed to ambient air for 2 weeks, the catalyst still maintains good catalytic activity.

[0803] Example 14: Synthesis of Phenylcycloheptane E

[0804]

[0805] The reaction is carried out in a glove box in an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) is added to P8 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) is added to the solution, and then supplemented by adding benzene to obtain a total concentration of 0.08 M bromocycloheptane. The reaction mixture is stirred at 25 ° C for 5 hours, and then a saturated NH4Cl aqueous solution is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. Phenylcycloheptane is obtained in a yield of> 99% using dodecane as an internal standard through gas chromatography.

[0806] This yield is higher than that obtained with Byers catalyst and the reaction is faster.

[0807] Example 15: Synthesis of Octylbenzene A

[0808]

[0809] The reaction is carried out in a glove box in an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) is added to P5 catalyst (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, and then supplemented by adding benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture is stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution is added. After extraction with EtOAc, the combined organic phase is dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography is performed to obtain octylbenzene in a yield of 71%.

[0810]

[0811] Example 16: Synthesis of Octylbenzene B

[0812]

[0813] The reaction is carried out in a glove box in an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) is added to P7 catalyst (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, and then supplemented by adding benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture is stirred at 25 ° C for 29 hours, and then a saturated NH4Cl aqueous solution is added. After extraction with EtOAc, the combined organic phase is dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography is performed to obtain octylbenzene in a yield of 91%.

[0814]

[0815] Example 17: Synthesis of 1-methyl-4-octylbenzene

[0816]

[0817] The reaction was carried out in a glove box under an inert atmosphere. A solution of 4-methylphenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis showed that 1-methyl-4-octylbenzene was obtained in a yield of 82%. Silica gel column chromatography analysis showed that 1-methyl-4-octylbenzene was obtained in a yield of 76%.

[0818]

[0819] Example 18: Synthesis of 1-methoxy-4-octylbenzene

[0820]

[0821] The reaction was carried out in a glove box under an inert atmosphere. A solution of 4-methoxyphenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25°C for 24 hours or 48 hours, and then a saturated aqueous NH4Cl solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis revealed that 1-methoxy-4-octylbenzene was obtained in a yield of 78% (after 24 hours) and 99% (after 48 hours). Silica gel column chromatography analysis revealed that 1-methoxy-4-octylbenzene was obtained in a yield of 76% (after 24 hours).

[0822]

[0823] Example 19: Synthesis of 1-phenoxy-4-octylbenzene

[0824]

[0825] The reaction was carried out in a glove box under an inert atmosphere. A solution of 4-phenoxyphenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25 ° C for 48 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis revealed that 1-phenoxy-4-octylbenzene was obtained in a yield of >96%.

[0826] Example 20: Synthesis of N,N-dimethyl-4-octylaniline

[0827]

[0828] The reaction was carried out in a glove box under an inert atmosphere. A solution of 4-(dimethylamino)phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain N, N-dimethyl-4-octylaniline in a yield of 90%.

[0829]

[0830] Example 21: Synthesis of 1-chloro-4-octylbenzene

[0831]

[0832] The reaction was carried out in a glove box under an inert atmosphere. A solution of 4-chlorophenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 80 ° C for 48 hours, and then a saturated aqueous NH4Cl solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 According to HNMR analysis, 1-chloro-4-octylbenzene was obtained in a yield of 40%.

[0833] Example 22: Synthesis of 1-nitro-4-octylbenzene

[0834]

[0835] The reaction was carried out in a glove box under an inert atmosphere. A solution of 4-nitrophenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 80 ° C for 48 hours, and then a saturated aqueous NH4Cl solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis revealed that 1-nitro-4-octylbenzene was obtained in a yield of 36%.

[0836] Example 23: Synthesis of 1-fluoro-4-octylbenzene

[0837]

[0838] The reaction is carried out in a glove box in an inert atmosphere. A solution of 4-fluorophenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) is added to P5 catalyst (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, and then supplemented by adding benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture is stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution 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 to obtain 1-fluoro-4-octylbenzene in a yield of 88%.

[0839]

[0840] Example 24: Synthesis of 1-octyl-3-(trifluoromethyl)benzene

[0841]

[0842] The reaction was carried out in a glove box in an inert atmosphere. A solution of 3-trifluoromethylphenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, and then supplemented by adding benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain 1-octyl-3-(trifluoromethyl)benzene in a yield of 83%.

[0843]

[0844] Example 25: Synthesis of 4-phenylpiperidine-1-carboxylic acid benzyl ester

[0845]

[0846] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 4-bromopiperidine-1-carboxylic acid benzyl ester (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 4-bromopiperidine-1-carboxylic acid benzyl ester. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain 4-phenylpiperidine-1-carboxylic acid benzyl ester in a yield of 95%.

[0847]

[0848] Example 26: Synthesis of 1-phenyladamantane A

[0849]

[0850] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromoadamantane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-chloroadamantane. The reaction mixture was stirred at 80° C. for 48 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain 1-phenyladamantane in a yield of 98%.

[0851]

[0852] Example 27: Synthesis of 1-phenyladamantane B

[0853]

[0854] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P7 catalyst (10 mol%) and EtNMeLi (2.2 eq). A solution of 1-bromoadamantane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-chloroadamantane. The reaction mixture was stirred at 80° C. for 48 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain 1-phenyladamantane in a yield of 79%.

[0855]

[0856] Example 28: Synthesis of 2-octylthiophene

[0857]

[0858] The reaction was carried out in a glove box under an inert atmosphere. A solution of 2-thienylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis showed that 2-octylthiophene was obtained in a yield of 78%.

[0859] Example 29: Synthesis of 6-cycloheptylquinoline

[0860]

[0861] The reaction was carried out in a glove box in an inert atmosphere. A solution of 6-quinolineboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M bromocycloheptane. The reaction mixture was stirred at 80 ° C for 48 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain 6-cycloheptylquinoline in a yield of 88%.

[0862]

[0863] Example 30: Synthesis of 1,1'-methylenediphenyl

[0864]

[0865] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P6 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of benzyl bromide (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M benzyl bromide. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated aqueous NH4Cl solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard. 1H NMR analysis showed that 1,1'-methylenediphenyl was obtained in a yield of 30%.

[0866] Example 31: Synthesis of 2-octylnaphthalene

[0867]

[0868] The reaction is carried out in a glove box in an inert atmosphere. A solution of naphthylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) is added to P5 catalyst (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, and then supplemented by adding benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture is stirred at 25 ° C for 48 hours, and then a saturated NH4Cl aqueous solution is added. After extraction with EtOAc, the combined organic phase is dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography is performed to obtain 2-octylnaphthalene in a yield of 93%.

[0869]

[0870] Example 32: Synthesis of Hexylbenzene

[0871]

[0872] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromohexane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromohexane. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain hexylbenzene in a yield of 90%.

[0873]

[0874] Example 33: Synthesis of Cyclopropylbenzene A

[0875]

[0876] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocyclopropane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M bromocyclopropane. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 HNMR analysis showed that cyclopropylbenzene was obtained in a yield of 45%.

[0877] Example 34: Synthesis of Cyclopropylbenzene B

[0878]

[0879] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P6 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocyclopropane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M bromocyclopropane. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 HNMR analysis showed that cyclopropylbenzene was obtained in a yield of 26%.

[0880] Example 35: Synthesis of 3-phenyloxetane

[0881]

[0882] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 3-bromooxetane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 3-bromooxetane. The reaction mixture was stirred at 25 °C for 24 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1H NMR analysis showed that 3-phenyloxetane was obtained in a yield of 69%. Silica gel column chromatography analysis showed that 3-phenyloxetane was obtained in a yield of 58%.

[0883]

[0884] Example 36: Synthesis of tert-Butylbenzene A

[0885]

[0886] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl chloride (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of tert-butyl chloride of 0.08 M. The reaction mixture was stirred at 25°C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 According to HNMR analysis, tert-butylbenzene was obtained in a yield of 54%.

[0887] Example 37: Synthesis of tert-Butylbenzene B

[0888]

[0889] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P6 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl chloride (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of tert-butyl chloride of 0.08 M. The reaction mixture was stirred at 25°C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 According to HNMR analysis, tert-butylbenzene was obtained in a yield of 32%.

[0890] Example 38: Synthesis of 2-cycloheptylthiophene

[0891]

[0892] The reaction was carried out in a glove box under an inert atmosphere. A solution of 2-thienylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of bromocycloheptane of 0.08 M. The reaction mixture was stirred at 25 ° C for 48 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis showed that 2-cycloheptylthiophene was obtained in a yield of 86%. Silica gel column chromatography analysis showed that 2-cycloheptylthiophene was obtained in a yield of 78%.

[0893]

[0894] Example 39: Synthesis of tert-butyl 4-(5-cycloheptylpyridin-2-yl)piperazine-1-carboxylate

[0895]

[0896] The reaction was carried out in a glove box under an inert atmosphere. A solution of 1-tert-butyl-4-(pyridin-2-yl)piperazineboronic acid pinacol ester (2 eq) in benzene (c=0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c=0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M chlorocycloheptane. The reaction mixture was stirred at 25° C. for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain tert-butyl 4-(5-cycloheptylpyridin-2-yl)piperazine-1-carboxylate in a yield of 92%.

[0897]

[0898] Example 40: Synthesis of tert-butyldimethyl(3-phenylpropoxy)silane

[0899]

[0900] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of (4-bromobutoxy) (tert-butyl) dimethylsilane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M (4-bromobutoxy) (tert-butyl) dimethylsilane. The reaction mixture was stirred at 25° C. for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain tert-butyldimethyl (3-phenylpropoxy) silane in a yield of 78%.

[0901]

[0902] Example 41: Synthesis of Cyclopentylbenzene A

[0903]

[0904] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocyclopentane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of bromocyclopentane of 0.08 M. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 According to HNMR analysis, cyclopentylbenzene was obtained with a yield of 99%. According to silica gel column chromatography analysis, cyclopentylbenzene was obtained with a yield of 70%.

[0905]

[0906] Example 42: Synthesis of Cyclopentylbenzene B

[0907]

[0908] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of chlorocyclopentane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M bromocyclopentane. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 According to HNMR analysis, cyclopentylbenzene was obtained in a yield of 99%.

[0909]

[0910] Example 43: Synthesis of Cyclopentylbenzene C

[0911]

[0912] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of iodocyclopentane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of iodocyclopentane of 0.08 M. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 HNMR analysis showed that cyclopentylbenzene was obtained in a yield of 77%. Silica gel column chromatography analysis showed that cyclopentylbenzene was obtained in a yield of 77%.

[0913] P5 can catalyze carbon-carbon bond formation with the previously defined brominated, chlorinated or iodinated Z-Hal halogenated derivatives.

[0914] Example 44: Synthesis of tert-butyl 3-phenylazetidine-1-carboxylate

[0915]

[0916] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl 3-bromoazetidine-1-carboxylate (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain tert-butyl 3-bromoazetidine-1-carboxylate at a total concentration of 0.08 M. The reaction mixture was stirred at 25 ° C for 48 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that tert-butyl 3-phenylazetidine-1-carboxylate was obtained in a yield of >99%. Silica gel column chromatography analysis showed that tert-butyl 3-phenylazetidine-1-carboxylate was obtained in a yield of 83%.

[0917]

[0918] Example 45: Synthesis of 2-octyl-1-p-toluenesulfonyl-1H-indole

[0919]

[0920] The reaction was carried out in a glove box under an inert atmosphere. A solution of boronic acid (1-toluenesulfonyl-1H-indol-2-yl) pinacol ester (2 eq) in benzene (c=0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c=0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25° C. for 48 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Silica gel column chromatography was performed to obtain 2-octyl-1-toluenesulfonyl-1H-indole in a yield of 69%.

[0921]

[0922] Example 46: Synthesis of tert-butyl 2-octyl-1H-indole-1-carboxylate

[0923]

[0924] The reaction was carried out in a glove box under an inert atmosphere. A solution of boronic acid (1-(tert-butoxycarbonyl)-1H-indol-2-yl) pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 80° C. for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that tert-butyl 2-octyl-1H-indole-1-carboxylate was obtained in a yield of 82%. Silica gel column chromatography analysis showed that tert-butyl 2-octyl-1H-indole-1-carboxylate was obtained in a yield of 50%.

[0925]

[0926] Example 47: Synthesis of 2-octyl-1-benzofuran

[0927]

[0928] The reaction was carried out in a glove box under an inert atmosphere. A solution of 2-benzofuranboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 80°C for 48 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that 2-octyl-1-benzofuran was obtained in a yield of 87%. Silica gel column chromatography analysis showed that 2-octyl-1-benzofuran was obtained in a yield of 82%.

[0929]

[0930] Example 48: Synthesis of 3-octylfuran

[0931]

[0932] The reaction was carried out in a glove box under an inert atmosphere. A solution of 3-furanboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 HNMR analysis showed that 3-octylfuran was obtained in a yield of 89%. Silica gel column chromatography analysis showed that 3-octylfuran was obtained in a yield of 82%.

[0933]

[0934] Example 49: Synthesis of (3-methylundecyl)benzene

[0935]

[0936] The reaction was carried out in a glove box in an inert atmosphere. A solution of 9-octyl-9-boranobicyclo[3.3.1]nonane (2 eq) in benzene (c=0.5 M) was added to a P5 catalyst (20 mol%) and NMe2Li (1.2 eq). A solution of (3-bromobutyl)benzene (1 eq) in benzene (c=0.25 M) was added to the solution, and then supplemented by adding benzene to obtain a total concentration of 0.08 M (3-bromobutyl)benzene. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc (3x 40 mL), the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. Using dodecane as an internal standard, (3-methylundecyl)benzene was obtained in a yield of 89% by gas chromatography. Silica gel column chromatography was performed to obtain (3-methylundecyl)benzene in a yield of 60%.

[0937]

[0938] Example 50: Synthesis of 4-(3-phenylpropyl)piperidine-1-carboxylic acid benzyl ester

[0939]

[0940] The reaction was carried out in a glove box under an inert atmosphere. A solution of 9-(2-phenylpropyl)-9-boranobicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) was added to the P5 catalyst (20 mol%) and NMe2Li (1.2 eq). A solution of 4-bromopiperidine-1-carboxylic acid benzyl ester (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 4-bromopiperidine-1-carboxylic acid benzyl ester. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that benzyl 4-(3-phenylpropyl)piperidine-1-carboxylate was obtained in a yield of 70%.

[0941] Example 51: Synthesis of tert-butyldimethyl((6-phenylhexyl)oxy)silane

[0942]

[0943] The reaction was carried out in a glove box under an inert atmosphere. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) was added to the P5 catalyst (20 mol%) and NMe2Li (1.2 eq). A solution of (4-bromobutoxy)(tert-butyl)dimethylsilane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M (4-bromobutoxy)(tert-butyl)dimethylsilane. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis revealed that tert-butyldimethyl((6-phenylhexyl)oxy)silane was obtained in a yield of 78%. Silica gel column chromatography analysis revealed that tert-butyldimethyl((6-phenylhexyl)oxy)silane was obtained in a yield of 44%.

[0944]

[0945] Example 52: Synthesis of (3-cyclopentylpropyl)benzene

[0946]

[0947] The reaction was carried out in a glove box under an inert atmosphere. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (20 mol%) and NMe2Li (1.2 eq). A solution of bromocyclopentane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M bromocyclopentane. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis revealed that (3-cyclopentylpropyl)benzene was obtained in a yield of 59%. Silica gel column chromatography analysis revealed that (3-cyclopentylpropyl)benzene was obtained in a yield of 53%.

[0948]

[0949] Example 53: Synthesis of (3-phenylpropyl)cycloheptane

[0950]

[0951] The reaction was carried out in a glove box under an inert atmosphere. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) was added to the P5 catalyst (20 mol%) and NMe2Li (1.2 eq). A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M bromocycloheptane. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that (3-phenylpropyl)cycloheptane was obtained in a yield of 74%. Silica gel column chromatography analysis showed that (3-phenylpropyl)cycloheptane was obtained in a yield of 65%.

[0952]

[0953] Example 54: Synthesis of 1-methyl-2-octylbenzene

[0954]

[0955] The reaction was carried out in a glove box under an inert atmosphere. A solution of 2-methylphenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 40 ° C for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis revealed that 1-methyl-2-octylbenzene was obtained in a yield of 99%. Silica gel column chromatography analysis revealed that 1-methyl-2-octylbenzene was obtained in a yield of 90%.

[0956]

[0957] Example 55: Synthesis of 1-methyl-3-octylbenzene

[0958]

[0959] The reaction was carried out in a glove box under an inert atmosphere. A solution of 3-methylphenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard 1 H NMR analysis revealed that 1-methyl-3-octylbenzene was obtained in a yield of 99%. Silica gel column chromatography analysis revealed that 1-methyl-3-octylbenzene was obtained in a yield of 94%.

[0960]

[0961] Example 56: Synthesis of tert-butyl 4-octylbenzoate

[0962]

[0963] The reaction was carried out in a glove box under an inert atmosphere. A solution of 4-(tert-butoxycarbonyl)phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 40°C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that tert-butyl 4-octylbenzoate was obtained in a yield of 99%. Silica gel column chromatography analysis showed that tert-butyl 4-octylbenzoate was obtained in a yield of 82%.

[0964]

[0965] Example 57: Synthesis of tert-butyl 3-(4-fluorophenyl)azetidine-1-carboxylate

[0966]

[0967] The reaction was carried out in a glove box under an inert atmosphere. A solution of 2 eq of 4-fluoroboric acid pinacol ester in benzene (c = 0.5 M) was added to the P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl 3-bromoazetidine-1-carboxylate (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain tert-butyl 3-bromoazetidine-1-carboxylate at a total concentration of 0.08 M. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that tert-butyl 3-(4-fluorophenyl)azetidine-1-carboxylate was obtained in a yield of 92%. Silica gel column chromatography analysis showed that tert-butyl 3-(4-fluorophenyl)azetidine-1-carboxylate was obtained in a yield of 83%.

[0968]

[0969] Example 58: Synthesis of tert-butyl 3-(4-ethoxyphenyl)azetidine-1-carboxylate

[0970]

[0971] The reaction was carried out in a glove box under an inert atmosphere. A solution of p-ethoxyboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to the P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of tert-butyl 3-bromoazetidine-1-carboxylate (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain tert-butyl 3-bromoazetidine-1-carboxylate at a total concentration of 0.08 M. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that tert-butyl 3-(4-ethoxyphenyl)azetidine-1-carboxylate was obtained in a yield of 87%. Silica gel column chromatography analysis showed that tert-butyl 3-(4-ethoxyphenyl)azetidine-1-carboxylate was obtained in a yield of 78%.

[0972]

[0973] Example 59: Synthesis of 1-cyclopentyl-2-(trifluoromethyl)benzene

[0974]

[0975] The reaction was carried out in a glove box under an inert atmosphere. A solution of 2-trifluoromethylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocyclopentane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of bromocyclopentane of 0.08 M. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 According to H NMR analysis, 1-cyclopentyl-2-(trifluoromethyl)benzene was obtained in a yield of 51%.

[0976] Example 60: Synthesis of 2-phenyl-2,3-dihydro-1H-indene

[0977]

[0978] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 2-bromo-2,3-dihydro-1H-indene (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 2-bromo-2,3-dihydro-1H-indene. The reaction mixture was stirred at 25 °C for 24 h, and then a saturated aqueous NH4Cl solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that 2-phenyl-2,3-dihydro-1H-indene was obtained in a yield of >99%. Silica gel column chromatography analysis showed that 2-phenyl-2,3-dihydro-1H-indene was obtained in a yield of 92%.

[0979]

[0980] Example 61: Synthesis of N,N,5-triphenylhexanamide

[0981]

[0982] The reaction was carried out in a glove box under an inert atmosphere. A solution of phenylboronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 5-bromo-N,N-diphenylhexanamide (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 5-bromo-N,N-diphenylhexanamide. The reaction mixture was stirred at 25 °C for 24 h, and then a saturated aqueous NH4Cl solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that N,N,5-triphenylhexanamide was obtained in a yield of 93%. Silica gel column chromatography analysis showed that N,N,5-triphenylhexanamide was obtained in a yield of 84%.

[0983]

[0984] Example 62: Synthesis of 1-methyl-5-octyl-1H-pyrazole

[0985]

[0986] The reaction was carried out in a glove box under an inert atmosphere. A solution of (1-methyl-1H-pyrazol-5-yl)boronic acid pinacol ester (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 25 ° C for 24 hours, and then a saturated aqueous NH4Cl solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 According to H NMR analysis, 1-methyl-5-octyl-1H-pyrazole was obtained in a yield of 15%.

[0987] Example 63: Synthesis of 5-octylbenzo[d][1,3]dioxole

[0988]

[0989] The reaction was carried out in a glove box under an inert atmosphere. A solution of benzo[d][1,3]dioxol-5-ylboronic acid pinacol ester (2 eq) in benzene (c=0.5 M) was added to P5 catalyst (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromooctane (1 eq) in benzene (c=0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 1-bromooctane. The reaction mixture was stirred at 80°C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that 5-octylbenzo[d][1,3]dioxole was obtained in a yield of >99%. Silica gel column chromatography analysis showed that 5-octylbenzo[d][1,3]dioxole was obtained in a yield of 91%.

[0990]

[0991] Example 64: Synthesis of 2-octyl-2,3-dihydro-1H-indene

[0992]

[0993] The reaction was carried out in a glove box under an inert atmosphere. A solution of 9-octyl-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) was added to the P5 catalyst (20 mol%) and NMe2Li (1.2 eq). A solution of 2-bromo-2,3-dihydro-1H-indene (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 2-bromo-2,3-dihydro-1H-indene. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that 2-octyl-2,3-dihydro-1H-indene was obtained in a yield of 37%. Silica gel column chromatography analysis showed that 2-octyl-2,3-dihydro-1H-indene was obtained in a yield of 30%.

[0994]

[0995] Example 65: Synthesis of (3-methylhexane-1,6-diyl)diphenyl

[0996]

[0997] The reaction is carried out in a glove box in an inert atmosphere. A solution of 9-(2-phenylpropyl)-9-boranobicyclo[3.3.1]nonane (2 eq) in benzene (c=0.5 M) is added to P5 catalyst (20 mol%) and NMe2Li (1.2 eq). A solution of (3-bromobutyl)benzene (1 eq) in benzene (c=0.25 M) is added to the solution, which is then supplemented by the addition of benzene to obtain a total concentration of 0.08 M (3-bromobutyl)benzene. The reaction mixture is stirred at 25° C. for 24 hours, and then a saturated NH4Cl aqueous solution is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure.

[0998] Analysis by silica gel column chromatography gave (3-methylhexane-1,6-diyl)diphenyl in a yield of 56%.

[0999]

[1000] Example 66: Synthesis of 5-methyl-N,N-diphenyltridecamide

[1001]

[1002] The reaction was carried out in a glove box under an inert atmosphere. A solution of 9-octyl-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) was added to the P5 catalyst (20 mol%) and NMe2Li (1.2 eq). A solution of 5-bromo-N,N-diphenylhexanamide (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M 5-bromo-N,N-diphenylhexanamide. The reaction mixture was stirred at 25 °C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis showed that 5-methyl-N,N-diphenyl tridecanamide was obtained in a yield of 60%. Silica gel column chromatography analysis showed that 5-methyl-N,N-diphenyl tridecanamide was obtained in a yield of 36%.

[1003]

[1004] Example 67: Synthesis of (3-cyclopropylpropyl)benzene

[1005]

[1006] The reaction was carried out in a glove box under an inert atmosphere. A solution of 9-(2-phenylpropyl)-9-borabicyclo[3.3.1]nonane (2 eq) in benzene (c = 0.5 M) was added to P5 catalyst (20 mol%) and NMe2Li (1.2 eq). A solution of bromocyclopropane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M bromocyclopropane. The reaction mixture was stirred at 25 ° C for 24 hours, 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. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 According to H NMR analysis, (3-cyclopropylpropyl)benzene was obtained in a yield of 30%.

[1007] Example 68: Synthesis of Phenylcycloheptane F

[1008]

[1009] The reaction was carried out in a glove box under an inert atmosphere. A solution of bromocycloheptane (1 eq) in benzene (c = 0.25 M) was added to the P5 catalyst (10 mol%). A solution of phenylmagnesium bromide (1.2 eq) in benzene (c = 0.5 M) was added to the solution, which was then supplemented by the addition of benzene to obtain a total concentration of 0.08 M bromocycloheptane. The reaction mixture was stirred at 25 ° C for 24 hours (non-optimized time), and then a saturated NH4Cl aqueous solution was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered and evaporated under reduced pressure. 1,3,5-Trimethoxybenzene was used as an internal standard. 1 H NMR analysis gave phenylcycloheptane in >99% yield.

Claims

1. Use of at least one compound of the following general formula (I) as a catalyst for a coupling reaction: in: ●A is selected from: ■-X group, wherein X is selected from chlorine atom, bromine atom, ■Group Wherein: M is a coordinating solvent, p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4, ■Group ● B, C, D and E are identical or different and 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 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; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

2. The use as a catalyst according to claim 1 for carrying out a reaction selected from carbon-carbon bonding reactions using organoboron or organomagnesium or organozinc or organotin, in particular for carrying out a Suzuki-Miyaura reaction.

3. The use according to claim 1, which is used for carrying out Suzuki-Miyaura reaction, Kumada reaction and Sonogashira reaction, in particular for carrying out Suzuki-Miyaura reaction.

4. Use of at least one compound of the following general formula (I) according to any one of claims 1 to 3: in: A is selected from: --X group, wherein X is selected from chlorine atom, bromine atom, -Group Wherein: M is a coordinating solvent, p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4, -Group B, C, D and E are identical or different and are selected from: hydrogen atoms, halogens, especially F or Cl, trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms, especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms, straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms; when A corresponds to the group hour, R1, R5, R6 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 or 2 or 4 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●When A corresponds to a -X group or a group When R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; The following compounds are not included:

5. The use according to any one of claims 1 to 4, which is the use of at least one compound of the following general formula (Ia) as a catalyst for a coupling reaction: in: ●X is selected from a chlorine atom and a bromine atom; ● B, C, D and E are identical or different and 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 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 10 carbon atoms; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

6. The use according to any one of claims 1 to 4, which is the use of at least one compound having the following general formula (Ib) as a catalyst for a coupling reaction: in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; ● B, C, D and E are identical or different and 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 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; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

7. The use according to any one of claims 1 to 4, which is the use of at least one compound of the following general formula (Ic) as a catalyst for a coupling reaction: in: B, C, D and E are identical or different and are selected from: hydrogen atoms, halogens, especially F or Cl, trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms, especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms, straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms; R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

8. The use according to any one of claims 1 to 5, which is the use of at least one compound of the following general formula (Ia) as a catalyst for a coupling reaction: The following general formula (Ia): in: ●X is selected from a chlorine atom and a bromine atom; ● B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, at least one of the groups B, C, D or E being different from the others; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and -R6 is different from R 10 and / or R7 is different from R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ia): in: ●X is selected from a chlorine atom and a bromine atom; ● B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, at least one of the groups B, C, D or E being different from the others; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9; or -R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ia): in: ●X is selected from a chlorine atom and a bromine atom; ● B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, at least one of the groups B, C, D or E being different from the others; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: -R1 is the same as R5, -R2 is the same as R4, -R6 and R 10 same, -R7 is the same as R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ia): in: ●X is selected from a chlorine atom and a bromine atom; B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and -R6 is different from R 10 and / or R7 is different from R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ia): in: ●X is selected from a chlorine atom and a bromine atom; B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9; or -R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ia): in: ●X is selected from a chlorine atom and a bromine atom; B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: -R1 is the same as R5, -R2 is the same as R4, -R6 and R 10 same, -R7 is the same as R9; ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

9. The use according to any one of claims 1 to 4 or 6, which is the use of at least one compound of the following general formula (Ib) as a catalyst for a coupling reaction: The following general formula (Ib): in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; ● B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, at least one of the groups B, C, D or E being different from the others; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and -R6 is different from R 10 and / or R7 is different from R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ib): in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; ● B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, at least one of the groups B, C, D or E being different from the others; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: ■ R1 is different from R5 and / or R2 is different from R4, and R6 is different from R 10 are the same and R7 is the same as R9; or ■R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ib): in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; ● B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, at least one of the groups B, C, D or E being different from the others; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: -R1 is the same as R5, -R2 is the same as R4, -R6 and R 10 same, -R7 is the same as R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ib): in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: R1 is different from R5 and / or R2 is different from R4, and ●R6 is different from R 10 and / or R7 is different from R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ib): in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9; or -R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ib): in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: -R1 is the same as R5, -R2 is the same as R4, -R6 and R 10 same, -R7 is the same as R9; ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

10. The use according to any one of claims 1 to 4 or 7, which is the use of at least one compound of the following general formula (Ic) as a catalyst for a coupling reaction: The following general formula (Ic): in: ● B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, at least one of the groups B, C, D or E being different from the others; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and -R6 is different from R 10 and / or R7 is different from R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ic): in: ● B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, at least one of the groups B, C, D or E being different from the others; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9; or -R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ic): in: ● B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, at least one of the groups B, C, D or E being different from the others; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: -R1 is the same as R5, -R2 is the same as R4, -R6 and R 10 same, -R7 is the same as R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ic): in: B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and -R6 is different from R 10 and / or R7 is different from R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ic): in: B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9; or -R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ic): in: B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: -R1 is the same as R5, -R2 is the same as R4, -R6 and R 10 same, -R7 is the same as R9; ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

11. The use according to any one of claims 1 to 8, which is the use of at least one compound of the following general formula as a catalyst for a coupling reaction: The following general formula (Ia): in: ●X is selected from a chlorine atom and a bromine atom; ● B, C, D and E are fluorine atoms; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ib): in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; ● B, C, D and E are fluorine atoms; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the following general formula (Ic): in: ● B, C, D and E are fluorine atoms; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

12. Use of a compound of formula (I) according to any one of claims 1 to 8, wherein the compound is selected from:

13. Compounds of the following general formula (I): A is selected from: --X group, wherein X is selected from chlorine atom, bromine atom, -Group in: M is a coordinating solvent, p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4, -Group B, C, D and E are identical or different and are selected from: hydrogen atoms, halogens, especially F or Cl, trifluoromethyl groups CF3, straight-chain or branched alkyl groups of 1 to 10 carbon atoms, especially straight-chain or branched alkyl groups of 2 to 4 carbon atoms, straight-chain or branched alkoxy groups of 1 to 10 carbon atoms, or straight-chain or branched dialkylamino groups of 2 to 20 carbon atoms; when A corresponds to the group hour, R1, R5, R6 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 or 2 or 4 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●When A corresponds to a -X group or a group hour, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; The following compounds are not included:

14. The compound according to claim 12, The compound has the following general formula (I): in: ●A, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 and G has the meaning defined in claim 11; B, C, D and E are identical or different and 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 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, and at least one of B, C, D or E is different from a hydrogen atom; Or the compound has the following general formula (I): in: A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, and R 10 and G has the meaning defined in claim 11; B, C, D and E are identical or different and 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 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, and at least one of B, C, D or E is a halogen, in particular F; Or the compound has the following general formula (I): in A, X, M, p, R1, R2, R3, R4, R5, R6, R7, R8, R9, and R 10 and G has the meaning defined in claim 11; ●B, C, D and E are fluorine atoms.

15. A compound: The compound has the following general formula (Ia): in: ●X is selected from a chlorine atom and a bromine atom; ● B, C, D and E are identical or different and 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 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; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the compound has the following general formula (Ia): wherein X and G have the meanings defined above, and B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and 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 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: - R1 is different from R5 and / or R2 is different from R4; and -R6 is different from R 10 and / or R7 is different from R9; Or the compound has the following general formula (Ia): wherein X and G have the meanings defined above, and B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and 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 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: -R1 is the same as R5, -R2 is the same as R4, -R6 and R 10 same, -R7 is the same as R9; Or the compound has the following general formula (Ib): in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; ● B, C, D and E are identical or different and 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 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; R1, R5, R6 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 2 or 4 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 1 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; The following compounds are not included: Or the compound has the following general formula (Ib): wherein X, M, p and G have the meanings defined above, and B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; R1, R5, R6 and R 10 is selected from the group consisting of: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 2 or 4 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9 are selected from the group consisting of: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and -R6 is different from R 10 and / or R7 is different from R9; Or the compound has the following general formula (Ib): wherein X, M, p and G have the meanings defined above, and B, C, D and E are selected from: hydrogen atoms, halogens, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group 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, with the proviso that B is identical to E and D is identical to C; R1, R5, R6 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 2 or 4 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9 are identical and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: -R1 is the same as R5, -R2 is the same as R4, -R6 and R 10 same, -R7 is the same as R9; The following compounds are not included:

16. A compound: The compound has the following general formula (Ic): in: ● B, C, D and E are identical or different and 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 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; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the compound has the following general formula (Ic): in: B, C, D and E are selected from: hydrogen atoms, hydrogen atoms, halogen, especially F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, especially 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and 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 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: -R1 is the same as R5, -R2 is the same as R4, -R6 and R 10 same, -R7 is the same as R9; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; Or the compound has the following general formula (Ic): in: B, C, D and E are selected from: hydrogen atoms, hydrogen atoms, halogen, especially F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, especially 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, with the proviso that B is identical to E and D is identical to C; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 is selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms, provided that: - R1 is different from R5 and / or R2 is different from R4, and R6 is the same as R 10 are the same and R7 is the same as R9; or -R6 is different from R 10 and / or R7 is different from R9, and R1 is the same as R5 and R2 is the same as R4; ● G is selected from a hydrogen atom, a straight chain or branched chain alkyl group of 1 to 5 carbon atoms.

17. A compound of formula (I) according to any one of claims 13 to 16, selected from:

18. The use according to any one of claims 1 to 12, which is the use of one or more of at least one of the compounds of formula (Ia), (Ib) or (Ic) for the synthesis of one of the compounds of the following formula: Wherein Y is selected from: ■Hydrogen atoms, ■ a straight-chain or branched alkyl group of 1 to 10 carbon atoms, ■ a straight-chain or branched alkoxy group of 1 to 10 carbon atoms, ■-OPh group, ■ an alkylamino group or a dialkylamino group substituted by one or two straight-chain alkyl groups of 1 to 10 carbon atoms, ■ halogen, in particular fluorine, chlorine or bromine, ■Nitro NO2 group, ■Trifluoromethyl group CF3, ■Group 19. The use according to any one of claims 1 to 12, which is the use of at least one of the compound of formula (Ia), the compound of formula (Ib) or the compound of formula (Ic) for carrying out the Suzuki-Miyaura reaction of compound (S1) with compound Z-Hal of formula (S2), Wherein W is selected from: -Phenyl wherein Y is selected from the group consisting of: a hydrogen atom, a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, an -OPh group, an alkylamino group or a dialkylamino group substituted by one or two straight-chain alkyl groups having 1 to 10 carbon atoms, a halogen, in particular a fluorine atom, a chlorine atom or a bromine atom, a nitro NO2 group, a trifluoromethyl group CF3, a group -2-Thienyl group -3-Furanyl group -2-Naphthyl group -6-Quinolyl group -Group -Group -Group -Group -Group -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, -Group And V is selected from: -Group Where q is equal to 0 or 1, -Group In the compound Z-Hal of formula (S2), Z is selected from: - a straight-chain or branched alkyl group having 1 to 20 carbon atoms or a cyclic group having 3 to 12 carbon atoms, in particular an octyl group, a hexyl group, a cycloheptyl group, a cyclopentyl group or a cyclopropyl group, -With style 1-adamantyl group, -With style The benzyl group, -Group -Group -Group -Group -Group -Group -Group -Group And Hal is selected from: - chlorine atoms, - bromine atoms, -Iodine atom.

20. A process for preparing a compound of formula (Ia) according to claim 15, in: ●X is selected from a chlorine atom and a bromine atom; ● B, C, D and E are identical or different and 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 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; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; The method comprises: a) a step of condensing a compound of formula (V) on a compound of formula (VI) to obtain a compound of formula (III); wherein B, C, D and E have the meanings defined above and F is a fluorine atom; wherein R1, R2, R3, R4 and R5 have the meanings defined above; wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom; b) an aromatic nucleophilic substitution step of the compound of formula (III) on the compound of formula (IV) to obtain a compound of formula (II): Among them, R6, R7, R8, R9 and R 10 has the meaning defined above; Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 has the meaning defined above; c) a step of sequentially adding n-butyllithium and iron (II) halide FeX2 to the compound of formula (II) to obtain a compound of formula (Ia).

21. A process for preparing a compound of formula (Ib) according to claim 15, in: ●X is selected from a chlorine atom and a bromine atom; ●M is the coordinating solvent; ●p is selected from 1, 2, 3, 4 or a decimal, and the decimal can be a value greater than 0 but less than 4; ● B, C, D and E are identical or different and 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 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 10 carbon atoms; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; The method comprises: a) a condensation step of a compound of formula (V) on a compound of formula (VI) to obtain a compound of formula (III), wherein B, C, D and E have the meanings defined above and F is a fluorine atom, wherein R1, R2, R3, R4 and R5 have the meanings defined above, wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom; b) an aromatic nucleophilic substitution step of the compound of formula (III) on the compound of formula (IV) to obtain a compound of formula (II): Among them, R6, R7, R8, R9 and R 10 has the meaning defined above, Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 has the meaning defined above, c) a step of sequentially adding n-butyllithium and iron (II) halide FeX2 to the compound of formula (II) to obtain a compound of formula (Ib).

22. A method for preparing a compound of formula (Ic) according to claim 16, in: ● B, C, D and E are identical or different and 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 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; ●R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are identical or different and are selected from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group having 1 to 10 carbon atoms, in particular a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched dialkylamino group having 2 to 20 carbon atoms; ●G is selected from hydrogen atoms, straight-chain or branched alkyl groups of 1 to 5 carbon atoms; The method comprises: a) a step of condensing a compound of formula (V) on a compound of formula (VI) to obtain a compound of formula (III), wherein B, C, D and E have the meanings defined above, and F is a fluorine atom; wherein R1, R2, R3, R4 and R5 have the meanings defined above; wherein B, C, D, E, G, R1, R2, R3, R4 and R5 have the meanings defined above, and F is a fluorine atom; b) an aromatic nucleophilic substitution step of the compound of formula (III) on the compound of formula (IV) to obtain a compound of formula (II): Among them, R6, R7, R8, R9 and R 10 has the meaning defined above; Among them, B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 has the meaning defined above; c) a step of sequentially adding n-butyllithium and iron (III) triacetylacetonate to the compound of formula (II) to obtain the compound of formula (Ic).

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