Use of iron-based compounds for the synthesis of borated compounds, and corresponding methods

Abstract

The present invention relates to the use of iron-based compounds for the synthesis of borated compounds, and the corresponding methods.

Description

[0001] Description

[0002] Title: Use of iron-based compounds for the synthesis of boron compounds, and the corresponding processes

[0003] Technical field

[0004] The present invention relates to the use of iron-based compounds for the synthesis of boron compounds, and to the corresponding methods.

[0005] State of the art

[0006] The carbon-boron bond is one of the most versatile bonds in synthetic organic chemistry, serving as a pivot for the preparation, under mild conditions, of a wide variety of major chemical functions (often from boronic esters). Although the pioneering work on organoboranes is often associated with Nobel Laureate in Chemistry H.C. Brown, it is their application in the Suzuki-Miyaura coupling that has highlighted the full potential of boron derivatives in synthesis. Indeed, this coupling, recognized by the award of the Nobel Prize in Chemistry in 2010, is one of the most commonly applied strategies in the pharmaceutical and agrochemical industries (fine chemicals sector) for the formation of carbon-carbon bonds.For example, in the pharmaceutical industry, the Suzuki-Miyaura coupling is used in nearly 25% of small molecule drug syntheses and accounts for 40% of carbon-carbon bond formation reactions.

[0007] Alkylboronic esters are most often prepared by hydroboration reactions of olefins or by transmetallation reactions of electrophilic boron derivatives with highly reactive compounds such as organolithium or organomagnesium compounds. However, significant limitations are associated with these methods, such as problems of regioselectivity control during hydroboration reactions of internal olefins and functional compatibility problems related to the use of highly reactive organolithium or organomagnesium compounds. These limitations considerably reduce the scope of applications of these methods.

[0008] The Miyaura borylation coupling reaction is currently dominated by catalysts based on palladium, a precious metal, but this pallado-catalyzed coupling has major drawbacks:

[0009] 1) It is mainly limited to the coupling between a borylation reagent and a halogenated or pseudo-halogenated partner carrying an sp hybridized carbon 2 (or even sp) leading to the formation of arylboronic esters. Indeed, the ease of elimination of the Pd(II)-alkyl intermediates formed during the coupling reaction slows down its extension to halogenated or pseudo-halogenated partners bearing sp hybridized carbons 3 . This therefore does not allow the use of this method to prepare alkylated boron compounds which are partners of choice for extensions of the Suzuki-Miyaura reaction with C(sp 3 ) which are very little reported today

[0010] 2) It uses an expensive and relatively toxic metal, which generates, for example, additional costs to meet strict regulations for palladium content in active pharmaceutical ingredients (typically < 5 ppm). In the context of sustainable development, it has also been estimated that the global warming potential (GWP) for the production of 1 kg of palladium is 3880 kg of CO2 equivalent (c-CCfi). For comparison, the production of 1 kg of iron has a GWP of only 1.5 kg of e-CCL.

[0011] Iron is one of the few base metals that has been successfully tested as a catalyst in industrial kilogram-scale cross-coupling processes. Although a few examples of iron-based catalysts for the Miyaura borylation reaction have been described in the state of the art, few have been reported to be effective for the coupling of halogenated partners bearing sp hybridized carbons. 3. In addition, they often rely on the use of activated boronic derivatives (using an organolithium or an organomagnesium) which represent significant limitations in terms of functional compatibility and / or they are limited in terms of field of applications. The invention aims to remedy the problem mentioned above and to catalyze the Miyaura borylation reaction.

[0012] An object of the invention is the use of iron imino-anilide complexes to catalyze the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

[0013] Another object of the invention is to provide preparation processes in which iron imino-anilide complexes are advantageous for preparing organoboron compounds.

[0014] Description of the invention.

[0015] The present invention relates to the use of at least one of the compounds of general formula (I) below: in which:

[0016] • A is chosen from:

[0017] ■ a group -X in which X is chosen from a chlorine atom a bromine atom

[0018] ■ a grouping in which:

[0019] M is a coordinating solvent p is chosen from 1, 2, 3, 4 or a decimal number which can vary from a value greater than 0 but less than 4 ■ a group

[0020] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0021] • Ri, R2, R3, Ri, Rs, FC. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0022] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

[0023] It was unexpectedly found that iron imino-anilide complexes could catalyze the Miyaura borylation reaction.

[0024] A can represent X, this group X being chosen from a chlorine or bromine atom, X(Li-X)- (M) p and (AcacR In case of steric hindrance due to the groups B, C, D, E, Ri, R2, R3, R4, Rs, ;, R7, Rs, Rg and Rio, A advantageously represents X.

[0025] When there is little or no steric hindrance due to the groups B, C, D, E, Ri, R2, R3, R4, Rs, Ri, R7, Rs, Rg and Rio, A advantageously represents XX(Li-X)-(M) p .

[0026] By "coordinating solvent" is meant any solvent capable of stabilizing the electron vacancy of a metal cation by giving up part of its electron density using a non-bonding doublet. The coordinating solvent is chosen from the group consisting of diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran. p can take the values ​​of 1, 2, 3, 4 or a decimal number which can vary from a value greater than 0 but less than 4, preferably 1.

[0027] When A represents two acetyloacetonate groups, the compounds do not degrade or lose their properties under the action of ambient air.

[0028] The term "ambient air" refers to the surrounding air naturally present in the atmosphere, the composition of which can vary depending on location or altitude.

[0029] By "linear" is meant the carbon atoms of the alkyl chain, with the exception of those located at the ends of the chain, are all linked one to one through a carbon-carbon bond, in such a way that each carbon atom has only two carbon-carbon bonds, the carbon atom at the beginning of the chain has only one carbon-carbon bond with the rest of the chain and the carbon atom located at the end of the chain has only one carbon-carbon bond.

[0030] The term "branched" means that each carbon atom in the alkyl chain can contain 3 to 4 carbon-carbon bonds.

[0031] The term "catalyst" means a chemical substance which, directly or after transformation by another chemical substance, activates or makes possible a chemical reaction.

[0032] The term "Miyaura borylation reaction" refers to the creation of a carbon-boron bond by cross-coupling between a halogenated or pseudo-halogenated derivative and a borylation reagent using a metal catalyst.

[0033] In a particular embodiment, the invention relates to the use as defined above, using a diboron compound, in particular a diboronic acid ester.

[0034] The term "diboron compound" means a compound bearing a boron-boron bond. By way of example and without limitation, diboron compounds may be diboronic acid esters, diborinic acid esters or diboranes.

[0035] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below: in which:

[0036] • X is chosen from a chlorine atom and a bromine atom

[0037] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 10 carbon atoms

[0038] • Ri, R2, R3, Ri, Rs, FL. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0039] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

[0040] This structure corresponds to the presence of steric hindrance around the iron atom due to the groups B, C, D, E, Ri, R2, R3, R4, Rs, Re, R7, Rs, Rg and Rio

[0041] To facilitate the understanding of what follows, we arbitrarily consider 3 axes of symmetry (I), (H) (III) as represented in the diagram below

[0042] Axis (I) creates symmetry between C and D, and between B and E. Axis (II) includes the carbon bearing R3 and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between Ri and R5, and between R2 and R4. Axis (III) includes the carbon bearing Rs and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between Re and Rio, and between R7 and Rg.

[0043] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ib) below: (Ib) in which:

[0044] • X is chosen from a chlorine atom and a bromine atom

[0045] • M is a coordinating solvent

[0046] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0047] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0048] • Ri, R2, R3, Ri, Rs, s, R7, Rs, Rg and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0049] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

[0050] This structure corresponds to the absence of steric hindrance, or to the presence of low steric hindrance around the iron atom due to the groups B, C, D, E, Ri, R2, R3, R4, Rs, Re, R7, Rs, Rg and Rio

[0051] Advantageously, the compound of formula (Ib) has the following formula:

[0052] To facilitate the understanding of what follows, we arbitrarily consider 3 axes of symmetry (I), (H) (III) as represented in the diagram below

[0053]

[0054] Axis (I) creates symmetry between C and D, and between B and E. Axis (II) includes the carbon bearing R3 and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between R1 and R5, and between R2 and R4. Axis (III) includes the carbon bearing FL and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between R1 and R10, and between R7 and FL.

[0055] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of the following general formula (Ic): in which:

[0056] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular E or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0057] • Ri, R2, Rs, R4, Rs, R- R7, Rs, R < and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0058] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

[0059] To facilitate the understanding of what follows, we arbitrarily consider 3 axes of symmetry (I), (H) (III) as represented in the diagram below

[0060] Axis (I) creates symmetry between C and D, and between B and E. Axis (II) includes the carbon bearing R3 and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between Ri and R5, and between R2 and R4. Axis (III) includes the carbon bearing Rs and the carbon bearing the nitrogen of the same phenyl group, and creates symmetry between Re and Rio, and between R7 and Rg.

[0061] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below: in which:

[0062] • X is chosen from a chlorine atom and a bromine atom

[0063] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF;, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others.

[0064] • Ri, R2, Rs, 4, Rs, ;, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0065] Ri is different from R5 and / or R2 is different from R4 and

[0066] Ri is different from Rio and / or R7 is different from Rg

[0067] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

[0068] This particular embodiment corresponds to an absence of symmetry with respect to the axis (I), the axis (II) and the axis (III). or of the following general formula (la): in which:

[0069] • X is chosen from a chlorine atom and a bromine atom

[0070] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0071] • R1, R2, R3, R4, Rs, R„. R7, Rs, Rg and R10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0072] ■ Ri is different from R5 and / or R2 is different from R4 and

[0073] ■ ; either identical to Rio and R7 or identical to FC or

[0074] ■ ; either different from Rio and / or R7 or different from Rg and

[0075] ■ Ri is identical to R5 and R2 is identical to R4

[0076] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

[0077] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I) and the axis (II), and the presence of a symmetry with respect to the axis (III). or of the following general formula (la):

[0078] in which:

[0079] • X is chosen from a chlorine atom and a bromine atom

[0080] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0081] • Ri, R2, Rs, 4, Rs, ;, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0082] Ri is identical to R5

[0083] R2 is identical to R4 Ri is identical to Rio R7 is identical to FC

[0084] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

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

[0086] in which:

[0087] • X is chosen from a chlorine atom and a bromine atom

[0088] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0089] • Ri, R2, Rs, 4, Rs, IC, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0090] Ri is different from R5 and / or R2 is different from R4 and; is different from Rio and / or R7 is different from FC

[0091] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

[0092] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I). It also corresponds to the absence of a symmetry with respect to the axis (II) and the axis (III). or of the following general formula (la):

[0093] in which:

[0094] • X is chosen from a chlorine atom and a bromine atom

[0095] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0096] • R1, R2, R3, R4, Rs, R„. R7, Rs, Rg and R10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0097] Ri is different from R5 and / or R2 is different from R4 and

[0098] Ri is identical to Rio and R7 is identical to FC or; is different from Rio and / or R7 is different from R, and

[0099] Ri is identical to R5 and R2 is identical to R4

[0100] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms

[0101] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I) and the axis (III). It also corresponds to the absence of a symmetry with respect to the axis (II). or of the following general formula (la):

[0102] in which:

[0103] • X is chosen from a chlorine atom and a bromine atom

[0104] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0105] • Ri, R2, R3, R4, Rs, ;, R7, s, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0106] Ri is identical to R5

[0107] R2 is identical to R4 Ri is identical to Rio R7 is identical to FC

[0108] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

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

[0110] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ib) below: in which:

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

[0112] • M is a coordinating solvent

[0113] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0114] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF;, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others.

[0115] • Ri, R2, Rs, 4, Rs, ;, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0116] Ri is different from R5 and / or R2 is different from R4 and

[0117] Ri is different from Rio and / or R7 is different from Rg

[0118] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

[0119] This particular embodiment corresponds to an absence of symmetry with respect to the axis (I), the axis (II) and the axis (III). or of the following general formula (Ib): in which:

[0120] • X is chosen from a chlorine atom and a bromine atom

[0121] • M is a coordinating solvent

[0122] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0123] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF;, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0124] • Ri, R2, Rs, R4, Rs, FC. R7, FC. FC and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0125] ■ Ri is different from R5 and / or R2 is different from R4 and

[0126] ■ Re is identical to Rio and R7 is identical to FC or

[0127] ■ IC is different from Rio and / or R7 is different from FC and

[0128] ■ Ri is identical to R5 and R2 is identical to R4

[0129] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms

[0130] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I) and the axis (II), and the presence of a symmetry with respect to the axis (III). or of the following general formula (Ib): in which:

[0131] • X is chosen from a chlorine atom and a bromine atom

[0132] • M is a coordinating solvent

[0133] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0134] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF;, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0135] • Ri, R2, Rs, Ri, Rs, IC, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0136] Ri is identical to R5

[0137] R2 is identical to R4; is identical to Rio R7 is identical to Rg

[0138] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

[0139] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I). It also corresponds to the presence of a symmetry with respect to the axis (II) and the axis (III) or of the following general formula (Ib): in which:

[0140] • X is chosen from a chlorine atom and a bromine atom

[0141] • M is a coordinating solvent

[0142] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0143] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0144] • Ri, R2, Rs, Ri, Rs, ;, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0145] Ri is different from R5 and / or R2 is different from R4 and

[0146] Ri is different from Rio and / or R7 is different from Rg

[0147] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

[0148] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I). It also corresponds to the absence of a symmetry with respect to the axis (II) and the axis (III) or of the following general formula (Ib): in which:

[0149] • X is chosen from a chlorine atom and a bromine atom

[0150] • M is a coordinating solvent

[0151] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0152] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0153] • Ri, R2, R3, Ri, Rs, Ri, R7, R, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0154] Ri is different from R5 and / or R2 is different from R and

[0155] Ri is identical to Rio and R7 is identical to Rg or

[0156] Ri is different from Rio and / or R7 is different from Rg and

[0157] Ri is identical to R5 and R2 is identical to R

[0158] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I) and the axis (III). It also corresponds to the absence of a symmetry with respect to the axis (II). or of the following general formula (Ib): in which:

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

[0160] • M is a coordinating solvent

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

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

[0163] • Ri, R2, R3, Ri, Rs, Ri, R7, R, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0164] Ri is identical to R5

[0165] R2 is identical to R Ri is identical to Rio R7 is identical to Rg

[0166] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3)-B. This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I), the axis (II) and the axis (III).

[0167] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of the following general formula (Ic): in which:

[0168] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0169] • Ri, R2, Rs, 4, Rs, R„. R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0170] Ri is different from R5 and / or R2 is different from R4 and

[0171] Ri is different from Rio and / or R7 is different from FC

[0172] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms

[0173] This particular embodiment corresponds to an absence of symmetry with respect to the axis (I), the axis (II) and the axis (III). or of the following general formula (the):

[0174] in which:

[0175] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0176] • R1, R2, R3, R4, Rs, R„. R7, Rs, Rg and R10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0177] Ri is different from R5 and / or R2 is different from R4 and

[0178] Ri is identical to Rio and R7 is identical to FC or; is different from Rio and / or R7 is different from R, and

[0179] Ri is identical to R5 and R2 is identical to R4

[0180] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms

[0181] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I) and the axis (II), and the presence of a symmetry with respect to the axis (III). or of the following general formula (the): in which:

[0182] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others

[0183] • Ri, R2, Rs, 4, Rs, IC, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0184] Ri is identical to R5

[0185] R2 is identical to R4; is identical to Rio R7 is identical to FC

[0186] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

[0187] This particular embodiment corresponds to the absence of symmetry with respect to the axis (I). It also corresponds to the presence of symmetry with respect to the axis (II) and the axis (III). or of the following general formula (the): in which:

[0188] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0189] • Ri, R2, Rs, 4, Rs, R„. R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0190] Ri is different from R5 and / or R2 is different from R4 and

[0191] Ri is different from Rio and / or R7 is different from FC

[0192] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

[0193] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I). It also corresponds to the absence of a symmetry with respect to the axis (II) and the axis (III) or of the following general formula (Ic): in which:

[0194] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0195] • R1, R2, R3, R4, Rs, R„. R7, Rs, Rg and R10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0196] Ri is different from R5 and / or R2 is different from R4 and

[0197] Ri is identical to Rio and R7 is identical to FC or; is different from Rio and / or R7 is different from R, and

[0198] Ri is identical to R5 and R2 is identical to R4

[0199] • G is chosen from a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atom(s).

[0200] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I) and the axis (III). It also corresponds to the absence of a symmetry with respect to the axis (II). or of the following general formula (Ic): in which:

[0201] • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C

[0202] • Ri, R2, R3, R4, Rs, ;, R7, s, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that:

[0203] Ri is identical to R5

[0204] R2 is identical to R4 Ri is identical to Rio R7 is identical to FC

[0205] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

[0206] This particular embodiment corresponds to the presence of a symmetry with respect to the axis (I), the axis (II) and the axis (III).

[0207] In a particular embodiment, the invention relates to the use, as defined above, of at least one of the compounds of general formula (Ia) below:

[0208] in which:

[0209] • X is chosen from a chlorine atom and a bromine atom

[0210] • B, C, D and E are fluorine atoms

[0211] • Ri, R2, Rs, R4, Rs, R- R7, Rs, R < and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0212] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms or of the following general formula (Ib): da • X is chosen from a chlorine atom and a bromine atom

[0213] • M is a coordinating solvent

[0214] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0215] • B, C, D and E are fluorine atoms

[0216] • Ri, R2, Rs, R4, Rs, R- R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0217] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ic): in which:

[0218] • B, C, D and E are fluorine atoms

[0219] • Ri, R2, R3, Ri, Rs, Rs. R7, Rs, R < and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0220] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B. This particular embodiment corresponds to the presence of 4 fluorine atoms on the phenyl group carrying the groups B, C, D and E. This has the consequence of modifying the electronic properties of the iron atom of the catalyst.

[0221] In a particular embodiment, the invention relates to the use of compounds of formula (I), as defined above, chosen from:

[0222] In a particular embodiment, the invention relates to the use of at least one of the compounds of formulas (Ia), (Ib) or (Ic) as defined previously, for the synthesis of one of the compounds of the following formula:

[0223]

[0224] In a particular embodiment, the invention relates to the use of at least one of the compounds of formulas (Ia), (Ib) or (Ic) as defined previously for carrying out a Miyaura borylation reaction from a compound (SI) in which Ri i is chosen from: a grouping in which q is equal to 0, 1 or 2 and Ri 2 represents a linear or branched alkyl group of 1 to 10 carbon atoms, in particular 1, a group with a compound of formula (S2): Z-Hal in which Z is chosen from: a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, in particular an octyl, hexyl, cycloheptyl or cyclopentyl group a 1-adamantyl group of formula a grouping: optionally substituted by one or two methyl groups, a group a group a group a group a group and Hal is chosen from: a chlorine atom a bromine atom an iodine atom a -OTs group.

[0225] In the compound (SI), there are 4 boron-oxygen bonds so that the Ru groups are linked two by two to form a cycle.

[0226] The Hal group can represent a halogen (chlorine, bromine and iodine) or a pseudohalogen (-OTs). The advantage of using a pseudohalogen compared to a halogen is the possibility of observing a better reactivity compared to that obtained with a halogen linked to the release of different anions into the medium.

[0227] Another subject of the invention relates to a process for preparing a compound of formula (X): in which Ri i is chosen from: a grouping in which q is equal to 0, 1 or 2 and Ri 2 represents a linear or branched alkyl group of 1 to 10 carbon atoms, in particular 1, a group and in which Ti, T2 and T3 are, identical or different, chosen from: a hydrogen atom, a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, optionally substituted by one or more phenyl groups or tert-butyldimethylsilyl ether group, a linear ether group of 1 to 20 carbon atoms, a linear alkylamine group of 1 to 20 carbon atoms, optionally protected, in particular by a tert-butoxycarbonyl group or a carboxybenzyl group a benzocyclopentane group, optionally Ti, T2 and T3 are linked together so as to form a polycycloalkane cycloalkane, in particular an adamantyl group, and optionally fused with a phenyl group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic ether group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic amine,provided that Ti, T2 and T3 do not simultaneously represent a hydrogen atom, comprising a step of bringing into contact a compound of Formula (XI):, with a compound of Formula (XII): in which Hal is chosen from: a chlorine atom a bromine atom an iodine atom a -OTs group, in the presence of a compound of formula (I): in which:

[0228] • A is chosen from:

[0229] ■ a group -X in which X is chosen from a chlorine atom a bromine atom

[0230] ■ a grouping in which:

[0231] M is a coordinating solvent p is chosen from 1, 2, 3, 4 or a decimal number which can vary from a value greater than 0 but less than 4

[0232] ■ a grouping

[0233] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0234] • Ri, R2, R3, Ri, Rs, FR. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0235] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) and a base.

[0236] As a non-limiting example, the Miyaura borylation reaction is carried out in the presence of a halogenated derivative (1 equivalent), a diboronic acid ester (2 equivalents), a base (1.2 equivalents) and the catalyst with stirring at 25°C for 48 hours. In a particular embodiment, the invention relates to a process for the preparation, as defined above, of a compound of formula (X): in which Ri i is chosen from: in which q is equal to 0, 1 or 2 and Ri 2 represents a linear or branched alkyl group of 1 to 10 carbon atoms, in particular 1, a group in which q and Ri 2 have the meaning defined above, and in which Ti, T2 and T3 are, identical or different, chosen from: a hydrogen atom, a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, optionally substituted by one or more phenyl groups or tert-butyldimethylsilyl ether group, a linear ether group of 1 to 20 carbon atoms, a linear alkylamine group of 1 to 20 carbon atoms, optionally protected, in particular by a tert-butoxycarbonyl group or a carboxybenzyl group a benzocyclopentane group, optionally Ti, T2 and T3 are linked together so as to form a polycycloalkane cycloalkane, in particular an adamantyl group, and optionally fused with a phenyl group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic ether group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic amine,provided that Ti, T2 and T3 do not simultaneously represent a hydrogen atom, comprising a step of bringing into contact a compound of Formula (XI):, with a compound of Formula (XII): in which Hal is chosen from: a chlorine atom a bromine atom an iodine atom a -OTs group, in the presence of a compound of formula (Ia): a chlorine atom a bromine atom • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 10 carbon atoms

[0237] • Ri, R2, R3, Ri, Rs, R„. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0238] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms and a base.

[0239] In a particular embodiment, the invention relates to a preparation process, as defined above, of a compound of formula (X): in which Ri 1 is chosen from: a group in which q is equal to 0, 1 or 2 and Ri 2 represents a linear or branched alkyl group of 1 to 10 carbon atoms, in particular 1, a group in which q and Ri 2 have the meaning defined above, a grouping and in which Ti, T2 and T3 are, identical or different, chosen from: a hydrogen atom, a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, optionally substituted by one or more phenyl groups or tert-butyldimethylsilyl ether group, a linear ether group of 1 to 20 carbon atoms, a linear alkylamine group of 1 to 20 carbon atoms, optionally protected, in particular by a tert-butoxycarbonyl group or a carboxybenzyl group a benzocyclopentane group, optionally Ti, T2 and T3 are linked together so as to form a polycycloalkane cycloalkane, in particular an adamantyl group, and optionally fused with a phenyl group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic ether group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic amine,provided that Ti, T2 and T3 do not simultaneously represent a hydrogen atom, comprising a step of bringing into contact a compound of Formula (XI): (XII):, in which Hal is chosen from: a chlorine atom a bromine atom an iodine atom a -OTs group, in the presence of a compound of formula (Ib): in which:

[0240] • X is chosen from a chlorine atom and a bromine atom

[0241] • M is a coordinating solvent

[0242] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0243] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0244] • Ri, R2, R3, Ri, Rs, R„. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0245] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, and a base.

[0246] In a particular embodiment, the invention relates to a process for the preparation, as defined above, of a compound of formula (X): in which Ri i is chosen from: a grouping in which q is equal to 0, 1 or 2 and Ri 2 represents a linear or branched alkyl group of 1 to 10 carbon atoms, in particular 1, a group and in which Ti, T2 and T3 are, identical or different, chosen from: a hydrogen atom, a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, optionally substituted by one or more phenyl groups or tert-butyldimethylsilyl ether group, a linear ether group of 1 to 20 carbon atoms, a linear alkylamine group of 1 to 20 carbon atoms, optionally protected, in particular by a tert-butoxycarbonyl group or a carboxybenzyl group a benzocyclopentane group, optionally Ti, T2 and T3 are linked together so as to form a polycycloalkane cycloalkane, in particular an adamantyl group, and optionally fused with a phenyl group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic ether group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic amine,provided that Ti, T2 and T3 do not simultaneously represent a hydrogen atom, comprising a step of bringing into contact a compound of Formula (XI): (XII):, in which Hal is chosen from: a chlorine atom a bromine atom an iodine atom a -OTs group, in the presence of a compound of formula (Ic): in which:

[0247] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0248] • Ri, R2, R3, Ri, Rs, FC. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0249] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s), and a base.

[0250] In a particular embodiment, the invention relates to a preparation process, as defined above, in which said process is carried out under an inert atmosphere.

[0251] In a particular embodiment, the invention relates to a preparation process, as defined above, in which said base is a lithium amide, in particular chosen from LiNMeEt, LiNMe2, LiNEt2, LiN(iPr)2, LiNTMS2, LiNPhMe, in particular LiNMeEt or LiNMe2, in particular LiNMeEt.

[0252] In this embodiment, the base is the conjugate base of an amine, for which the counterion is a lithium cation.

[0253] In a particular embodiment, the invention relates to a preparation process, as defined above, in which said process is carried out in solution in a non-coordinating apolar solvent, in particular chosen from benzene, hexane, toluene, cyclohexane or methylcyclohexane.

[0254] In a particular embodiment, the invention relates to a preparation process, as defined above, wherein said process is carried out in solution in a coordinating solvent chosen from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, tert-amylmethyl ether or 1,4-dioxane, in particular chosen from tetrahydrofuran, tert-butylmethylether or tert-amylmethyl ether.

[0255] The advantage of using a coordinating solvent is that the electron vacancy of the iron atom is stabilized by the non-bonding pairs of the solvent molecules

[0256] In a particular embodiment, the invention relates to a preparation process, as defined above, in which said base is LiNMeEt and said process is carried out in solution in tert-amylmethyl ether.

[0257] In a particular embodiment, the invention relates to a preparation process, as defined above, in which said base is LiNMeEt and said process is carried out in solution in tetrahydrofuran. In a particular embodiment, the invention relates to a preparation process, as defined above, in which said base is LiNMe2 and said process is carried out in solution in tert-amylmethyl ether.

[0258] In a particular embodiment, the invention relates to a preparation process, as defined above, in which said compound of formula (I), (Ia), (Ib) or (Ic) is present in an amount of 5 to 35% in molar concentration relative to the compound of formula (XII), in particular 10 to 20% in molar concentration.

[0259] By "5 to 35% molar concentration" we mean: 5 to 10% molar concentration, 10 to 15% molar concentration, 15 to 20% molar concentration, 20 to 25% molar concentration, 25 to 30% molar concentration and 30 to 35% molar concentration.

[0260] The expression "in molar concentration relative to the compound of formula (XII)" means that the compound of Formula (I), (Ia), (Ib) or (Ic) is present at a level of 5 to 35 mol% depending on the number of moles of the compound of Formula (XII). By way of example and in a non-limiting manner, if the compound of Formula (XII) is present at a level of one mole, then the compound of formula (I), (Ia), (Ib) or (Ic) is present at a level of 0.05 to 0.35 moles.

[0261] The catalysts of the invention can be prepared as follows.

[0262] The present description relates to a process for the preparation of a compound of formula (Ia) as defined above: in which:

[0263] • X is chosen from a chlorine atom and a bromine atom

[0264] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0265] • Ri, R2, R3, Ri, Rs, FL. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms comprising a step of sequential addition of n-butyllithium then iron (II) halide FeX2 to a compound of formula (II) in which B, C, D, E, G, Ri, R2, R3, R4, Rs, R«, R7, Rs, Rg and Rio have the meanings indicated above.

[0266] In this embodiment, the addition reaction here consists of the deprotonation of the secondary amine function of compound (II) located between two phenyl groups in order to create the N-Fe bond. Lithium does not coordinate to compound (Ia) due to the steric hindrance around the iron atom due to the groups B, C, D, E, Ri, R2, R3, R4, Rs, Re, R7, Rs, Rg and Rio. The compound (Ia) obtained is sensitive to oxygen and must be stored under inert atmospheric conditions.In another embodiment, the present description relates to a preparation process, as defined above, in which the above-mentioned addition step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran, from -78°C to 25°C, preferably at -78°C, for 30 minutes, then 2 hours at 25°C, then 15 hours with stirring. The expression "ethereal solvent" designates a solvent in which there is at least one ether function.

[0267] This sequential addition can be carried out either in a single solvent, or in a first solvent for the addition of n-butyllithium, then after evaporation of this solvent, in a second solvent for the addition of FeX2.

[0268] As a non-limiting example, this step of sequential addition of n-butyllithium and FeX2 (1 / 1) can be carried out for the addition of n-butyllithium in hexane, then for the addition of FeX2 in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole.

[0269] As a non-limiting example, this step of sequential addition of n-butyllithium and FeX2 (1 / 1) can be carried out for the addition of n-butyllithium in a non-coordinating apolar solvent in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, then for the addition of FeX2 in tetrahydrofuran.

[0270] By "non-coordinating apolar solvent" we mean a solvent whose barycenter of the sums of the electronegativity differences are the same,

[0271] As a non-limiting example, this step of adding n-butyllithium and Fe2 chloride (1 / 1) can be carried out in tetrahydrofiirane at temperatures of -78°C to 25°C, preferably -78°C to -30°C for 30 minutes, then 2 hours from -78°C to 25°C, preferably from 0°C to 25°C, then 15 hours from -78°C to 25°C, preferably from 0°C to 25°C with stirring.

[0272] In another embodiment, the present description relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (II): in which B, C, D, E, G, R1, R2, R3, R4, Rs, R7, Rs, Rg and R10 have the meanings indicated above, said step comprising a step of aromatic nucleophilic substitution of a compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom on a compound of formula (IV): in which Re, R7, Rs, Rg, and Rio have the meanings indicated above to obtain said compound of formula (II) In this embodiment, the aromatic nucleophilic substitution occurs via the lithium amide of compound (IV) replaces the fluorine of compound (III).

[0273] In another embodiment, the present description relates to a preparation process, as defined above, in which the above-mentioned aromatic nucleophilic substitution step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran and at a temperature of 25°C to 125°C, preferably at 25°C.

[0274] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0275] In another embodiment, the present description relates to a preparation process, as defined above, in which the above-mentioned aromatic nucleophilic substitution step is carried out in a non-coordinating apolar solvent, in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, preferably in toluene and at a temperature of 25°C to 125°C, preferably at 25°C or 90°C.

[0276] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0277] In another embodiment, the present description relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (III) wherein B, C, D, E, G, R1, R2, Rs, R4, and R5 have the meanings indicated above, and F is a fluorine atom, said step comprising a condensation reaction of a compound of formula (V) in which B, C, D, and E have the meanings indicated above, and F is a fluorine atom on a compound of formula (VI): in which R1, R2, Rs, R4, and R5 have the meanings indicated above to obtain said compound of formula (III)

[0278] In this embodiment, the condensation step forming compound (III) is carried out from an aldehyde, compound (V) and an amine, compound (IV).

[0279] In another embodiment, the present description relates to a preparation process, as defined above, in which the above condensation step is carried out, at a temperature of 0°C to 150°C, in a non-coordinating apolar or alcoholic solvent, in particular chosen from hexane, toluene, benzene, cyclohexane, methylcyclohexane, butan-1-ol, butan-2-ol, isobutanol, tert-butanol, propan-2-ol, isopropanol, methanol, or ethanol, preferably hexane at 25°C, or preferably toluene at 150°C, or preferably ethanol at 90°C.

[0280] The term "alcoholic solvent" refers to a solvent that contains a hydroxyl function.

[0281] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1) is carried out in the presence of MgSCL (0.08 mol%) in hexane at temperatures of 25°C to 75°C, preferably at 25°C.

[0282] As a non-limiting example, this condensation of an aldehyde and an amine is carried out in the presence of para-toluenesulfonic acid (1 / 1.1 / 0.01) in toluene at temperatures of 25°C to 150°C, preferably at 150°C.

[0283] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1,1) is carried out in ethanol at temperatures of 25°C to 90°C, preferably at 25°C.

[0284] In another embodiment, the present description relates to a process for the preparation, as defined above, of a compound of formula (Ia) in which:

[0285] • X is chosen from a chlorine atom and a bromine atom

[0286] B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0287] Ri, R2, R3, Ri, Rs, R .. R7, Rs, R < and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0288] G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atoms comprising: a) a step of condensation of a compound of formula (V) in which in which B, C, D, and E have the meanings indicated above and F is a fluorine atom on a compound of formula (VI): in which R1, R2, Rs, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom b) a step of aromatic nucleophilic substitution of said compound of formula (III) on a compound of formula (IV): in which Re, R7, Rs, Rg, and Rio have the meanings indicated above to obtain the compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, Rs, R«, R7, Rs, Rg and R10 have the meanings indicated above c) a step of sequential addition of n-butyl lithium then iron (II) halide FeX2 to said compound of formula (II) to obtain the compound of formula (Ia).

[0289] In another embodiment, the present description relates to a process for the preparation, as defined above, of a compound of formula (Ib):

[0290] in which:

[0291] • X is chosen from a chlorine atom and a bromine atom

[0292] • M is a coordinating solvent

[0293] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0294] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0295] • Ri, R2, R3, Ri, Rs, FR. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0296] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms comprising a step of sequential addition of n-butyllithium then iron (II) halide FeX2 to a compound of formula (II)

[0297] in which B, C, D, E, G, Ri, R2, R3, R4, Rs, R;, R7, Rs, Rg and Rio have the meanings indicated above.

[0298] In this embodiment, the addition reaction here consists of the deprotonation of the secondary amine function of compound (II) located between two phenyl groups in order to create the N-Fe bond. A first X atom linked to iron coordinates to a lithium atom, itself already coordinated by another X atom. This coordination can occur in the absence or presence of a small steric hindrance around the iron atom due to the groups B, C, D, E, Ri, R2, R3, R, Rs, R;, R7, Rs, Rg and Rio. The resulting compound is sensitive to ambient air and must be stored under inert atmospheric conditions.

[0299] In another embodiment, the present description relates to a preparation process, as defined above, in which the above-mentioned addition step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran, from -78°C to 25°C, preferably at -78°C, for 30 minutes, then 2 hours at 25°C, then 15 hours at 25°C with stirring. This sequential addition can be carried out either in a single solvent, or in a first solvent for the addition of n-butyllithium, then after evaporation of this solvent, in a second solvent for the addition of FeCX2.

[0300] As a non-limiting example, this step of sequential addition of n-butyllithium and FeX2 (1 / 1) can be carried out for the addition of n-butyllithium in hexane, then for the addition of FeX2 in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole.

[0301] As a non-limiting example, this step of sequential addition of n-butyllithium and FeX2 (1 / 1) can be carried out for the addition of n-butyllithium in a non-coordinating apolar solvent in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, then for the addition of FeX2 in tetrahydrofuran.

[0302] As a non-limiting example, this step of adding n-butyllithium and FcCL (1 / 1) can be carried out in tetrahydrofiirane at temperatures of -78°C to 25°C, preferably -78°C to -30°C for 30 minutes, then 2 hours from -78°C to 25°C, preferably from 0°C to 25°C, then 15 hours from -78°C to 25°C, preferably from 0°C to 25°C with stirring.

[0303] In another embodiment, the present description relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (II):

[0304] in which B, C, D, E, G, R1, R2, R3, R4, Rs, R7, Rs, Rg and R10 have the meanings indicated above, said step comprising a step of aromatic nucleophilic substitution of a compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom on a compound of formula (IV): in which Re, R7, Rs, Rg, and Rio have the meanings indicated above to obtain said compound of formula (II).

[0305] In this embodiment, the aromatic nucleophilic substitution occurs via the lithium amide of compound (IV) substituting for the fluorine of compound (III).

[0306] In another embodiment, the present description relates to a preparation process, as defined above, in which the above-mentioned aromatic nucleophilic substitution step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran and at a temperature of 25°C to 125°C, preferably at 25°C.

[0307] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0308] In another embodiment, the present description relates to a preparation process, as defined above, in which the above-mentioned aromatic nucleophilic substitution step is carried out in a non-coordinating apolar solvent, in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, preferably in toluene and at a temperature of 25°C to 125°C, preferably at 25°C or 90°C.

[0309] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0310] In another embodiment, the present description relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (III) in which B, C, D, E, G, R1, R2, Rs, R4, and R5 have the meanings indicated above, and F is a fluorine atom, said step comprising a condensation reaction of a compound of formula (V) in which B, C, D, and E have the meanings indicated above, and F is a fluorine atom on a compound of formula (VI): in which R1, R2, Rs, R4, and R5 have the meanings indicated above to obtain said compound of formula (III).

[0311] In this embodiment, the condensation step forming the imine of compound (III) is carried out from an aldehyde, compound (V) and an amine, compound (IV).

[0312] In another embodiment, the present description relates to a preparation process, as defined above, in which the above condensation step is carried out, at a temperature of 0°C to 150°C, in a non-coordinating apolar or alcoholic solvent, in particular chosen from hexane, toluene, benzene, cyclohexane, methylcyclohexane, butan-1-ol, butan-2-ol, isobutanol, tert-butanol, propan-2-ol, isopropanol, methanol, or ethanol, preferably hexane at 25°C, or preferably toluene at 150°C or preferably ethanol at 90°C.

[0313] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1) is carried out in the presence of MgSCfi (0.08 mol%) in hexane at temperatures of 25°C to 75°C, preferably at 25°C.

[0314] As a non-limiting example, this condensation of an aldehyde and an amine is carried out in the presence of para-toluenesulfonic acid (1 / 1.1 / 0.01) in toluene at temperatures of 25°C to 150°C, preferably at 150°C.

[0315] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1,1) is carried out in ethanol at temperatures of 25°C to 90°C, preferably at 25°C.

[0316] In another embodiment, the present description relates to a process for the preparation, as defined above, of a compound of formula (Ib) in which • X is chosen from a chlorine atom and a bromine atom

[0317] • M is a coordinating solvent

[0318] • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4

[0319] • B, C, D, and E, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 10 carbon atoms

[0320] • Ri, R2, R3, Ri, Rs, FR. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0321] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) comprising: a) a step of condensation of a compound of formula (V) in which in which B, C, D, and E have the meanings indicated above and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom b) a step of aromatic nucleophilic substitution of said compound of formula (III) on a compound of formula (IV): in which Re, R7, Rs, Rg, and Rio have the meanings indicated above to obtain the compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, Rs, R«, R7, Rs, Rg and R10 have the meanings indicated above c) a step of sequential addition of n-butyl lithium then iron (II) halide FeX2 to said compound of formula (II) to obtain the compound of formula (Ib).

[0322] In a particular embodiment, the present description relates to a process for the preparation, as defined above, of a compound of formula (Ic): in which:

[0323] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0324] • Ri, R2, R3, Ri, Rs, R„. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0325] • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms comprising a step of sequential addition of n-butyl lithium, then iron (III) tris-acetylacetonate to a compound of formula (II)

[0326] in which B, C, D, E, G, R1, R2, R3, R4, Rs, R7, Rs, Rg and R10 have the meanings indicated above to obtain said compound of formula (Ic).

[0327] In this embodiment, the addition reaction here consists of the deprotonation of the secondary amine function of compound (II) located between two phenyl groups in order to create the N-Fe bond. The compounds of formula (Ie) thus obtained are stable in ambient air.

[0328] In another embodiment, the present description relates to a preparation process, as defined above, in which the above-mentioned addition step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran, from -78°C to 25°C, preferably at 25°C, then 16 hours at 25°C with stirring.

[0329] This sequential addition can be carried out either in a single solvent, or in a first solvent for the addition of n-butyllithium, then after evaporation of this solvent, in a second solvent for the addition of Fe(acac)3.

[0330] As a non-limiting example, this step of sequential addition of n-butyllithium and Fe(acac)s (1 / 1) can be carried out for the addition of n-butyllithium in hexane, then for the addition of Fe(acac)s in a cyclic or non-cyclic ethereal solvent, in particular chosen from tetrahydrofuran, diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole.

[0331] As a non-limiting example, this step of sequential addition of n-butyllithium and Fe(acac)s (1 / 1) can be carried out for the addition of n-butyllithium in a non-coordinating apolar solvent in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, then for the addition of Fe(acac)s in tetrahydrofiirane.

[0332] As a non-limiting example, this step of adding n-butyllithium and Fe(acac)s (1 / 1) can be carried out in tetrahydrofiirane at temperatures from -78°C to 25°C, preferably from -78°C to -30°C for 30 minutes, then 2 hours from -78°C to 25°C, preferably from 0°C to 25°C, then 16 hours from -78°C to 25°C, preferably at 25°C.

[0333] In another embodiment, the present description relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (II): in which B, C, D, E, G, R1, R2, R3, R4, Rs, R7, Rs, Rg and R10 have the meanings indicated above, said step comprising a step of aromatic nucleophilic substitution of a compound of formula (III) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom on a compound of formula (IV): in which Re, R7, Rs, Rg, and Rio have the meanings indicated above to obtain said compound of formula (II).

[0334] In this embodiment, the aromatic nucleophilic substitution occurs via the lithium amide of compound (IV) substituting for the fluorine of compound (III).

[0335] In another embodiment, the present description relates to a preparation process, as defined above, in which the above-mentioned aromatic substitution step is carried out in a cyclic or non-cyclic ethereal solvent, in particular chosen from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethyl ether, tert-butylethyl ether, methyl tetrahydrofuran, 1,4-dioxane, methoxycyclopentane, tert-amyl methyl ether or anisole, preferably tetrahydrofuran and at a temperature of 25°C to 125°C, preferably at 25°C.

[0336] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (1 / 1) is carried out in tetrahydrofuran at temperatures of 25°C to 125°C, preferably of 25°C to 75°C.

[0337] In another embodiment, the present description relates to a preparation process, as defined above, in which the above-mentioned addition step is carried out in a non-coordinating apolar solvent, in particular chosen from benzene, hexane, toluene, cyclohexane, methylcyclohexane, preferably in toluene and at a temperature of 25°C to 125°C, preferably at 25°C or 90°C.

[0338] As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures of 25°C to 125°C, preferably 90°C to 125°C. As a non-limiting example, this aromatic nucleophilic substitution of compound (IV) on compound (III) (2.5 / 1) is carried out in toluene at temperatures of 25°C to 125°C, preferably 25°C to 75°C.

[0339] In another embodiment, the present description relates to a preparation process, as defined above, comprising a step of preparing a compound of formula (III) in which B, C, D, E, G, R1, R2, Rs, R4, and R5 have the meanings indicated above, and F is a fluorine atom said step, comprising a step of condensation of a compound of formula (V) in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings indicated above, and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above, to obtain said compound of formula (III).

[0340] In this embodiment, the step of forming the imine of compound (III) is carried out from an aldehyde, compound (V) and an amine, compound (IV).

[0341] In another embodiment, the present description relates to a preparation process, as defined above, in which the above condensation step is carried out, at a temperature of 0°C to 150°C, in a non-coordinating apolar or alcoholic solvent, in particular chosen from hexane, toluene, benzene, cyclohexane, methylcyclohexane, butan-1-ol, butan-2-ol, isobutanol, tert-butanol, propan-2-ol, isopropanol, methanol or ethanol, preferably hexane at 25°C, or preferably in toluene at 150°C or preferably in ethanol at 90°C.

[0342] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1) is carried out in the presence of MgSCfi (0.08 mol%) in hexane at temperatures of 25°C to 75°C, preferably at 25°C.

[0343] As a non-limiting example, this condensation of an aldehyde and an amine is carried out in the presence of para-toluenesulfonic acid (1 / 1.1 / 0.01) in toluene at temperatures of 25°C to 150°C, preferably at 150°C.

[0344] As a non-limiting example, this condensation of an aldehyde and an amine (1 / 1,1) is carried out in ethanol at temperatures of 25°C to 90°C, preferably at 25°C.

[0345] In another embodiment, the present description relates to a process for the preparation, as defined above, of a compound of formula (Ic) in which:

[0346] • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0347] • Ri, R2, Rs, R4, Rs, R- R7, Rs, R < and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms

[0348] • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) comprising: a) a step of condensation of a compound of formula (V) in which B, C, D, and E have the meanings indicated above, and F is a fluorine atom on a compound of formula (VI): in which R1, R2, R3, R4, and R5 have the meanings indicated above to obtain the compound of formula (III) in which B, C, D, E, G, R1, R2, Rs, R4, and R5 have the meanings indicated above, and F is a fluorine atom b) a step of aromatic nucleophilic substitution of said compound of formula (III) on a compound of formula (IV): in which Re, R7, Rs, Rg, and Rio have the meanings indicated above to obtain the compound of formula (II) in which B, C, D, E, G, R1, R2, R3, R4, Rs, R«, R7, Rs, Rg and R10 have the meanings indicated above, c) a step of sequential addition of n-butyl lithium then iron (III) tris-acetylacetonate to said compound of formula (II) to obtain said compound of formula (Ic).

[0349] Examples

[0350] Materials and methods

[0351] The 'H and 13 C were made at 298 K on a Bruker AM250, AV300 or AV360 MHz Bruker spectrometer. The NMR spectra of the 7 Li and du 19 F were made at 295 K on a Bruker 300 and 250 spectrometer respectively. The chemical shifts of the 'H spectra were measured using an internal reference which is residual protonated CHCl3 in CDCl3 (7.24 ppm) or residual protonated benzene in benzene-de (7.16 ppm).

[0352] Elemental analyses were performed at Analytische Laboratorien GMBH in Lindlar, Germany.

[0353] High-resolution mass spectra were measured by electrospray ionization (ESI) with a Bruker MicrOTOFq time-of-flight mass spectrometer or a Waters LCT spectrometer using electrospray ionization-time-of-flight (ESI-TOF) mass spectrometry.

[0354] The following are general procedures for the preparation of compounds of formula (Ia), (II) and (III). in which the groups R2, R4, R7 and R< represent a hydrogen atom, and the groups Ri, R3, R5, Re, Rs and Rio have the meanings indicated in the following table:

[0355] Rdt Rdt Rdt

[0356] HHHHH Cl iPr Me Me E 66^1 33^ 57

[0357] H OMe HHE Cl iPr iPr EE '61< 72^1 s?

[0358] HHHH Me Cl iPr iPr HE - 26^1 2S

[0359] [a] Procedure Al. [b] Procedure A2. [c] Procedure A3, [d] Procedure El. [g] Procedure B2, 90

[0360] °C. [f| Procedure B2, 25 °C. [g] Procedure B3. [h] Procedure Cl.

[0361] Procedure A1: The appropriate aniline derivative (1 eq) is added with stirring to a solution of the appropriate 2-fluorobenzaldehyde derivative (1 eq) and MgSCL in hexane (c = 1.6 M) at 25 °C. The solution is stirred for 2 h at this temperature then filtered, concentrated under reduced pressure and cooled to -20 °C to give the corresponding compound (III) in the form of yellow crystals.

[0362] Procedure A2: In a Dean-Stark apparatus, para-toluenesulfonic acid (0.01 eq) is added with stirring to a solution of the appropriate 2-fluorobenzaldehyde derivative (1 eq) and the appropriate aniline derivative (1.1 eq) in toluene (c = 0.40 M). The solution is heated to 150 °C for 15 h. Then, the solution is cooled to 25 °C before the addition of a saturated aqueous solution of Na2COs. The aqueous phase is separated and extracted with Et2O. The organic phases are combined, dried over MgSCl, filtered and concentrated under reduced pressure to give a slightly yellow oil. Recrystallization from hexane at -20 °C gives the corresponding compound (III) as yellow crystals.

[0363] Procedure A3: 2,6-Diisopropylamine (1.1 eq) is added to a solution of perfluorobenzaldehyde (1 eq) in EtOH (c = 1.5 M) at 25 °C and the solution is stirred at this temperature for 2 h. The solution is concentrated under reduced pressure and then cooled to -20 °C, the corresponding compound (III) is obtained in the form of yellow crystals.

[0364] Procedure Bl: A solution of n-butyllithium (n-Buli) (1 eq) is added with stirring to a solution of the appropriate aniline derivative (1 eq) in tetrahydrofuran (THF) (c = 1 M) at -78 °C. The solution is stirred for 15 h and then cannulated into a solution of the appropriate compound (III) (1 eq) in THF (c = 1 M) at 25 °C. The solution is stirred for 2 h at this temperature and then water is added. The aqueous phase is separated and extracted with hexane. The organic phases are combined, dried over MgSCl, filtered and concentrated under reduced pressure to give a brown oil. Recrystallization from hot ethanol or at -20 °C gives the corresponding compound (II) as yellow crystals.

[0365] Procedure B2: The appropriate compound (III) (1 eq) is added to a suspension of lithium 2,6-diisopropylphenylamide (2.5 eq) in toluene (10 mL) at 25 °C. The solution is heated at 90 °C with stirring for 72 h or at 25 °C for 48 h. Then, the solution is cooled to 25 °C before the addition of a saturated aqueous solution of Na2COs. The aqueous phase is separated and extracted with Et2O. The organic phases are combined, dried over MgSCl, filtered and concentrated under reduced pressure to give a slightly brown oil. Recrystallization from hot EtOH gives the corresponding compound (II) as pale yellow crystals.

[0366] Procedure B3: TiCl (0.5 eq) was added to a solution of 2,6-diisopropylaniline (3 eq) in hexane (c = 1 M) while stirring at 0 °C. The solution was stirred at 25 °C for 24 h. Then the solution was heated to reflux and a solution of 2-fluoroacetophenone (1 eq) in hexane (c = 2.6 M) was added. The solution was heated to reflux for 16 h. A brown solid appeared in the solution. The solution was filtered and the solid was washed with hexane. The organic phases were combined and washed with water. The aqueous phase was separated and then extracted with hexane. The organic phases were combined and dried with MgSCl, filtered and concentrated in vacuo until a yellow oil appeared. n-BuLi (1 eq) was added to a stirred solution of 2,6-diisopropylaniline (1 eq) in THF (c = 1 M) at -78 °C.The solution is stirred for 18 hours, then is deposited using a cannula into the solution of the yellow oil previously synthesized in THF at 25°C. The solution is stirred for 2 hours at 25°C. Then water is added to the medium. The aqueous phase is separated, then extracted with Et2O. The organic phases are combined, dried with MgSCL, filtered and the solvent is evaporated under vacuum to obtain a slightly brown oil. The slightly brown oil is recrystallized from hot ethanol to obtain the corresponding compound (II) in the form of a pale white powder.

[0367] Procedure Cl: n-BuLi (1.6 eq) is added with stirring to a solution of the appropriate compound (III) (1 eq) in THF (c = 0.4 M) at -78 °C. The cooling bath is removed 30 min after the addition. The solution is stirred for 2 h at 25 °C. Then, FcC (1 eq) is added. The solution is stirred for 15 h at 25 °C and then the solvent is evaporated under reduced pressure. The residual solid is washed with hexane and then extracted with Et2O. The dark red solution is concentrated and cooled to -20 °C to give a dark red powder of the corresponding compound (Ia).

[0368] EXAMPLE 1: Synthesis of (£)-A-mesityl-l-(perfluorophenyl)methanimine

[0369] 2,4,6-Trimethylaniline (2.3 mL, 16.05 mmol) was added to a solution of perfluorobenzaldehyde (1.8 mL, 15 mmol) in EtOH (10 mL) at 25 °C and the solution was refluxed (90 °C) for 16 h. After evaporation of the solvent and recrystallization from Et2O at -20 °C, (L)-A-mcsityl- l - (perfluorophenyl)methanimine (4.4 g, 14 mmol, 94%) was obtained as yellow crystals. 'H NMR (360 MHz, CDCl3, 25 °C) 5 ppm 8.36 (s, 1H, NH), 6.91 (s, 2H, H Ar), 2.30 (s, 3H, -Me), 2.15 (s, 6H, o-Me). ). 13 C NMR (90 MHz, CDCl3, 25°C) 5 151.6, 148.4, 134.2, 129.0, 126.5, 20.8, 18.1. MS- HR (ESI) m / z calculated for C16H13F5N [M+H] + 314.0963, found: 314.0957.

[0370] EXAMPLE 2: Synthesis of (£)- / V-(2-ethylphenyl)-l-(pentafluorophenyl)methanimine

[0371] 2-Ethylaniline (2.0 mL, 16.5 mmol) was added to a solution of perfluorobenzaldehyde (1.8 mL, 15 mmol) in EtOH (10 mL) at 25 °C and the solution was refluxed (90 °C) for 16 h. After evaporation of the solvent and recrystallization from ether at -20 °C, (E)-N-(2 -ethylphenyl)- 1- (pentafluorophenyl)methanimine (3.7 g, 13.3 mmol, 82%) was obtained as yellow crystals. 'H NMR (360 MHz, CDCI3, 25 °C) ô ppm 8.59 (s, 1H, NH), 7.34-7.26 (m, 3H, H Ar), 7.03-6.98 (m, 1H, H Ar), 2.84 (q, 2H, J = 7.5 Hz, CH2CH3), 1.26 (t, 3H, J = 7.5 Hz, CH2CH3). 13 C NMR (90 MHz, CDCh, 25°C) δ 149.8, 147.3, 138.8, 129.0, 127.4, 126.9, 116.9, 24.8, 14.9. MS-HR (ESI) m / z calculated for C15H11F5N [M+H] + 300.0806, found: 300.0799.

[0372] EXAMPLE 3: Synthesis of (£)-2,3^4,5-tetrafluoro- / V-mesityl-6-((mesitylimino)methyl)aniline

[0373] (£)-JV-mesityl-l-(perfluorophenyl)methanimine (2.5 g, 8 mmol) was added to a solution of lithium (2,4,6-trimethylphenyl)amide (2.8 g, 20 mmol) in toluene (16 mL) and stirred for 48 h at 25°C. After the addition of saturated NaHCO; solution (50 mL), the aqueous phase was extracted with EtOAc (50 mL). The organic phases were combined, dried over MgSCl, filtered and concentrated under reduced pressure. Recrystallization from MeOH at -20°C was carried out and gave pale yellow crystals of the product (£)-2,3,4,5-tetrafluoro- / V-mesityl-6- ((mesitylimino)methyl)aniline (3.3 g, 7.7 mmol, 96%) 'H NMR (360 MHz, CDCI3, 25 °C) ô ppm 10.94 (s, 1H, NH), 8.66 (s, 1H, ArCHN), 6.92-6.90 (m, 4H, H Ar), 2.30 (s, 6H, p-Me), 2.22 (s, 6H, o-Me), 2.15 (s, 6H, o-Me). 13 C { 19F} NMR (100 MHz, CDCI3, 25°C) ô ppm 157.8, 147.5, 137.6, 135.9, 135.8, 135.4, 135.3, 135.1, 134.1, 131.9, 129.5, 129.0, 128.5, 127.3, 102.5, 20.9, 20.7, 18.4. MS-HR (ESI) m / z calculated for C25H25F4N [M+H] + 429.1948, found: 429.1934.

[0374] EXAMPLE 4: Synthesis of (£)- / V-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3,4,5,6- tetrafluoroaniline

[0375] (E)-N-(2-ethylphenyl)-l-(pentafluorophenyl)methanimine (2.4 g, 8 mmol) was added to a solution of lithium 2-(ethylphenyl)amide (2.5 mL, 20 mmol) in toluene (16 mL) and stirred for 48 h at 25°C. After the addition of saturated NaHCOs solution (50 mL), the aqueous phase was extracted with EtOAc (50 mL). The organic phases were combined, dried over MgSO4, filtered, and concentrated under reduced pressure. Recrystallization from MeOH at -20°C gave pale yellow crystals of the product (£)-A-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3, 4,5,6-tetrafluoroaniline (2.7 g, 6.75 mmol, 84%). 'H NMR (360 MHz, CDC13, 25 °C) ô ppm 10.91 (s, 1H, NH), 8.84 (s, 1H, ArCHN), 7.32-7.23 (m, 4H, H Ar), 7.21-7.12 (m, 2H, H Ar), 7.04-7.00 (m, 2H, H Ar), 2.81-2.70 (m, 4H, CH2CH3), 1.26 (t, 3H, J = 7.5 Hz, CH2CH3), 1.13 (t, 3H, J = 7.5 Hz, CH2CH3). 13 C { 19F} NMR (100 MHz, CDC13, 25°C) ô ppm 153.9, 149.1, 139.3, 137.7, 137.0, 133.7, 132.9, 131.3, 128.9, 128.6, 127.1, 127.0, 126.1, 124.8, 122.2, 118.2, 106.0, 24.9, 24.7, 14.8, 14.2. MS-HR (ESI) m / z calculated for C 23 H2IF4N2[M+H] + 401.1635, found: 401.1621.

[0376] EXAMPLE 5: Synthesis of P5

[0377] n-BuLi (2.5 M in hexane) (2 mL, 5 mmol) was added with stirring to a solution of ( / ■.')- 2,3,4,5-tetrafluoro-A-mesityl-6-((mesitylimino)methyl)aniline (2.1 g, 5 mmol) in THF (10 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 4 h at 25 °C. Then, FeCl2 (0.63 g, 5 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane or pentane (10 mL) and then extracted with Et2O (25 mL). The ethereal solution was filtered, concentrated, and replaced with hexane (20 mL). After adding a few drops of THF and cooling to -20°C, red crystals of product P5 (2.09 g, 3.0 mmol 60%) were obtained. Elemental analysis calculated for C 25 H 23Cl2F4FeLiN2(C4H8O)2: C, 56.19; H, 5.57; N, 3.97, trouvé: C, 54.53; H 5.92; N 4.15. ’H RMN (360 MHz, C6D6-50 pL THF-ds, 25 °C) ô ppm 71.05 (s, 3H, p-Me), 33.95 (s, 3H, p-Me), 25.51 (s, 2H, m-H Ar), 24.01 (br s, 6H, o-Me), 14.16 (s, 2H, m-H Ar), 4.37 (br s, 12H, THF), 2.15 (br s, 6H, o-Me), 1.69 (br s, 12H, THF). 7Li NMR (117 MHz, C6D6-50pL THF-ds, 25 °C) ô ppm 239.6 (br s).

[0378] EXEMPLE 6 : Synthèse de P6

[0379] n-BuLi (2.5 M in hexane) (2 mL, 5 mmol) was added with stirring to a solution of (E)-N-(2-ethylphenyl)-2-(((2-ethylphenyl)imino)methyl)-3,4,5,6-tetrafluoroaniline (2 g, 5 mmol) in THF (10 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 4 h at 25 °C. Then, FcCF (0.63 g, 5 mmol) was added. The solution was stirred overnight and the solvent was evaporated under reduced pressure. The residual solid was washed with hexane or pentane (10 mL) and extracted with Et2O (25 mL). The ether solution was filtered, concentrated, and replaced with hexane (20 mL). After adding a few drops of THF and cooling to -20°C, red crystals of the product P6 (1.1 g, 1.6 mmol, 35%) were obtained. Elemental analysis calculated for C23Hi9C12F4FeLiN2(C4H8O)2: C, 54.97 H, 5.21; N, 4.14, found: C, 51.13; H 4.90; N 4.40. 1H NMR (250 MHz, C6D6-50 pL THF-ds, 25 °C) 5 ppm 34.58 (br s, 1H, H Ar), 26.05 (s, 1H, H Ar), 23.66 (s, 1H, H Ar), 14.94 (s, 2H, H Ar), 12.90 (s, 1H, H Ar), 4.94 (br s, 10H, THF), 1.91 (br s, 10H, THF), -7.84 (br s, 4H, CH2), -10.46 (br s, 6H, CH3), -37.60 (s, 1H, H Ar), -71.64 (s, 1H, H Ar), -87.68 (br s, 1H, ArCHN).

[0380] EXEMPLE 7 : Synthèse de P7

[0381] n-BuLi (2.5 M in hexane) (2.8 mL, 7 mmol) was added with stirring to a solution of (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesitylimino)methyl)aniline (3 g, 7 mmol) in THF (15 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 4 h at 25 °C and concentrated under reduced pressure to give (E)-2,3,4,5-tetrafluoro-N-mesityl-6-((mesitylimino)methyl)aniline lithium amide. To a solution of Fe(acac)3 (2.1g, 6 mmol) in THF (12 ml) is added with stirring the lithium amide of (£)-2,3,4,5-tetrafluoro-A-mesityl-6-((mesitylimino)methyl)aniline (2.6g, 6 mmol) in THF (6 ml) at 25 °C, then the solution is stirred for 16 h at the same temperature. The red solution becomes dark green. After cooling to - 20 °C, filtration on celite is carried out as well as evaporation, the solid is washed with cold pentane to give a dark green powder of the product P7 (2g, 2.9 mmol, 50%).Elemental analysis calculated for C35H3?F4FeN2O4: C, 61.68 H, 5.47; N, 4.11, found: C, 59.9; H 5.39; N 3.92. 'H NMR (250 MHz, C6D6-50 pL THF-ds 25 °C) 62.91 (br s, 3H, p-Me), 50.93 (br s, 3H, p-Me), 28.92 (br s, 14H, o-Me and mH Ar), 20.99 (br s, 14H, Me and mH Ar), -25.10 (br s, 2H, CH) (deviations in integration values ​​may be observed due to the width of the signals).

[0382] EXAMPLE 8: Synthesis of P8

[0383] n-BuLi (2.5 M in hexane) (0.8 mL, 2.0 mmol) was added with stirring to a solution of (£)- 2.3.4.5-tctrafliioro-A'-mcsityl-6-((mcsitylimino)mcthyl)anilinc (0.77 g, 1.8 mmol) in THF (3.6 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 4 h at 25 °C. Then, FeBr2 (0.389 g, 1.8 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane or pentane and extracted with Et2O. The ether solution was filtered, concentrated and replaced with hexane. After adding a few drops of THF and cooling to -20°C, red crystals of the product P8 (0.63 g, 0.8 mmol, 44%) were obtained. 'H NMR (250 MHz, C6D6-50 pL THF-ds, 25 °C) 5 ppm 71.09 (s, 3H, p-Me), 33.98 (s, 3H, p-Me), 27.42 (br s, 8H, mH Ar and o-Me), 15.91 (s, 2H, mH Ar), 4.43 (br s, 14H, THF), 2.13 (br s, 6H, o-Me), 1.75 (br s, 14H, THF).7 Li NMR (117 MHz, C6D6- 50pL THF-ds, 25 °C) 5 ppm 162.66 (br s).

[0384] EXAMPLE 9: Synthesis of P9

[0385] n-BuLi (2.5 M in hexane) (1.2 mL, 3.0 mmol) was added with stirring to a solution of (£)-JV-(2-(mesitylamino)benzylidene)-2,4,6-trimethylaniline (1.0 g, 2.8 mmol) in THF (7 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 2 h at 25 °C. Then, FeCl (0.356 g, 2.8 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane and extracted with Et2O. The ethereal solution was filtered, concentrated and cooled to -20°C to give dark red crystals of product P9 (1.12 g, 1.77 mmol, 75%). Elemental analysis calculated for C33H4iCl2FeLiN2O2: C, 62.78; H, 6.55; N, 4.44, found: C, 62.54; H 6.68; N 4.47. IR (cm 1): 2953, 2925, 1622, 1605, 1570, 1521, 1461, 1433, 1377, 1333, 1260, 1207, 1224, 1182, 1162, 1143, 1041, 922, 873, 854, 793, 748, 672. 'H NMR (250MHz, C6D6-50 pL THF-ds, 25 °C) 5 ppm 95.8 (br s, 1H, m-H Ar), 85.7 (br s, 1H, m-H Ar), 58.4 (s, 3H, p-Me), 34.6 (s, 3H, p-Me), 24.5 (s, 2H, m-H Ar), 15.2 (br s, 8H, m-H Ar recouvrement avec o-Me), 4.6 (s, 8H, THF), 1.8 (s, 8H, THF), 0.5 (br s, 6H, o-Me), -39.9 (s, 1H, ArCHN), -44.8 (br s, 1H, p-H Ar). 7 Li NMR (117 MHz, C6D6-50pL THF-ds, 25 °C) 5238.2 (br s).

[0386] EXEMPLE 10 : Synthèse de P10

[0387] n-BuLi (2.5 M in hexane) (1.0 mL, 2.5 mmol) was added with stirring to a solution of (£)-A'-(2-(((2.6-diisopropylphenyl)imino)methyl)phenyl)-2.4.6-trimethylanilinc (1.0 g, 2.5 mmol) in THF (10 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 2 h at 25 °C. Then, FeCl2 (0.318 g, 2.5 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane and extracted with Et2O. The ethereal solution was filtered, concentrated and cooled to -20°C to give dark red crystals of product P10 (0.96 g, 1.42 mmol, 57%). Elemental analysis calculated for C36H47Cl2FeLiN2O2: C, 64.20; H, 7.03; N, 4.16, found: C, 63.83; H 7.16; N 4.22.IR (cm’ ’): 2957, 2961, 2925, 2876, 1659, 1605, 1517, 1461, 1431, 1375, 1364, 1335, 1300, 1257, 1204, 1168, 1157, 1125, 1108, 1096, 1043, 924, 888, 873, 856, 837, 810, 797, 751, 735, 678. ’H NMR (250MHz, C6D6-50 pL THF-ds, 25 °C) 5 ppm 93.6 (br s, 1H, m-H Ar), 84.0 (br s, 1H, m-H Ar), 56.6 (s, 3H, p- Me), 23.8 (s, 2H, m-H Ar), 15.2 (s, 2H, m-H Ar), 14.2 (br s, 6H, o-Me), 6.9 (s, 8H, THF), 2.5 (s, 8H, THF), 1.0 (br s, 6H, CHMeMe), -16.4 (br s, 6H, CHMeMe), -35.6 (s, 1H, ArCHN), -39.0 (br s, 1H, p- H Ar), -43.9 (br s, 1H, p-H Ar), -49.0 (br s, 2H, CHMeMe). 7 Li NMR (117 MHz, C6D6-50pL THF-ds, 25 °C) 5 ppm 258.2 (br s).

[0388] EXEMPLE 11 : Synthèse de Pli

[0389] n-BuLi (2.5 M in hexane) (1.4 mL, 3.5 mmol) was added with stirring to a solution of (£)-A'-(2-((2.6-diisopropylphenyl)amino)bcnzylidcnc)-2.6-diisopropylanilinc (1.5 g, 3.4 mmol) in THF (15 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 2 h at 25 °C. Then, FeCl2 (0.431 g, 3.4 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane and extracted with Et2O. The ethereal solution was filtered, concentrated and cooled to -20°C to give red crystals of the product Pli (1.91 g, 2.66 mmol, 78%). Elemental analysis calculated for C39H53Cl2FeLiN2O2: C, 65.46; H, IA , N, 3.91, found: C, 64.91; H 7.37; N 3.95. 'H NMR (250MHz, C6D6-50 pL THF-ds, 25 °C) 5 ppm 91.4 (s, 1H, mH Ar), 83.3 (s, 1H, mH Ar), 23.3 (s, 2H, mH Ar), 14.5 (s, 2H, mH Ar), 4.5 (br s, 8H, THF), 4.3 (br s, 6H, CHMeMe), 1.8 (br s, 8H, THF), 1.4 (br s, 6H, CHMeMe), -8.6 (s, 1H, o-H Ar), -16.4 (br s, 6H, CHMeMe), -19.1 (br s, 6H, CHMeMe), - 29.5 (br s, 2H, CHMeMe), -34.5 (s, 1H, p-H Ar), -39.5 (s, 1H, p-H Ar), -42.1 (br s, 1H, ArCHN), -51.6 (br s, 2H, CHMeMe), -56.5 (s, 1H, p-H Ar). 7 Li NMR (117 MHz, C6D6-50pL THF-ds, 25 °C) 5 ppm 269.8 (br s).

[0390] EXEMPLE 12 : Synthèse de P12

[0391] n-BuLi (1.6 M in hexane) (1.2 mL, 1.91 mmol) was added with stirring to a solution of ( / ■.')- A-(2,6-diisopropylphenyl)-2-(((2,6-diisopropylphenyl)imino)methyl)-4-methoxyaniline (0.9 g, 1.91 mmol) in THF (9 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 2 h at 25 °C. Then, FeCl (0.242 g, 1.91 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane and then extracted with Et2O. The ether solution was filtered, concentrated and cooled to -20°C to give dark red crystals of product P12 (1.24 g, 1.65 mmol, 87%). Elemental analysis calculated for C^HssCEFeLi^CE: C, 64.44; H, 7.44; N, 3.76, found: C, 63.00; H 7.47; N 4.25. 'H NMR (250MHz, C6D6-50 pL THF-ds, 25 °C) 6 ppm 91.1 (s, 1H, mH Ar), 91.9 (s, 1H, mH Ar), 24.9 (s, 2H, mH Ar), 17.0 (s, 3H, OMe), 15.5 (s, 2H, mH Ar), 4.6 (s, 6H, CHMeMe), 4.3 (br s, 8H, THF), 1.7 (br s, 8H, THF), 1.2 (br s, 6H, CHMeMe), -15.2 (br s, 6H, CHMeMe), -17.8 (br s, 6H, CHMeMe), -33.4 (s, 1H, ArCHN), -42.4 (br s, 1H, p-H Ar), -54.9(s, 1H, p-H Ar). 7 Li NMR (117 MHz, C6D6-50pL THF-ds, 25 °C) ô ppm 277.4 (br s)

[0392] EXEMPLE 13 : Synthèse de P13

[0393] n-BuLi (2.5 M in hexane) (0.75 mL, 1.85 mmol) was added with stirring to a solution of (£)-JV-(2,6-diisopropylphenyl)-2-(((2,6-diisopropylphenyl)imino)methyl)-5-fluoroaniline (0.84 g, 1.84 mmol) in THF (8.5 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 2 h at 25 °C. Then, FeCl (0.233 g, 1.84 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane and extracted with Et2O. The ethereal solution was filtered, concentrated and cooled to -20°C to give red crystals of the product P13 (0.347 g, 0.473 mmol, 26%). Elemental analysis calculated for CsîTfoCEFFeLi^Ch: C, 63.86; H, 7.15; N, 3.82, found: C, 63.47; H 7.18; N 3.89. IR (cm 1): 2958, 2927, 2871, 1614, 1575, 1522, 1463, 1435, 1422, 1386, 1322, 1311, 1254, 1209, 1181, 1165, 1105, 1095, 1059, 1041, 1001, 935, 910, 888, 848, 798, 782, 770, 736, 721. 'H NMR (250MHz, C6D6, 25 °C) 5 ppm 93.8 (br s, 1H, m-H Ar), 92.2 (br s, 1H, m-H Ar), 20.6 (s, 2H, m-H Ar),

[0394] 13.1 (s, 2H, m-H Ar), 4.9 (br s, 8H, THF), 3.8 (s, 6H, CHMeMe), 1.9 (br s, 14H, CHMeMe; THF), -

[0395] 17.2 (br s, 6H, CHMeMe), -19.7 (br s, 6H, CHMeMe), -34.5 (s, 1H, ArCHN), -36.7 (br s, 1H, p-H Ar), -37.1 (s, 1H, p-H Ar), -54.5 (s, 1H, p-H Ar). 7 Li NMR (117 MHz, C6D6-50pL THF-ds, 25 °C) ô ppm 273.5 (br s).

[0396] EXEMPLE 14 : Synthèse de P14

[0397] n-BuLi (2.5 M in hexane) (0.9 mL, 2.2 mmol) was added with stirring to a solution of (£)-A-(l-(2-((2,6-diisopropylphenyl)amino)phenyl)ethylidene)-2,6-diisopropylaniline (1.0 g, 2.2 mmol) in THF (10 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 2 h at 25 °C. Then, FeCl (0.28 g, 2.2 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane and extracted with Et2O. The ether solution is filtered, concentrated and cooled to -20°C to give red crystals of the product P14 (0.445 g, 0.61 mmol, 28%). Elemental analysis calculated for C^HssChFeLi^C: C, 65.85; H, 7.60; N, 3.84, found: C, 66.02; H 7.68; N 3.96. 'H NMR (250MHz, C6D6, 25 °C) 5 ppm 79.3 (br s, 1H, mH Ar), 22.4 (s, 2H, mH Ar), 14.3 (s, 2H, mH Ar), 5.4 (br s, 6H, CHMeMe), 4.7 (s, 8H, THF), 1.8 (br s, 8H, THF), -0.3 (br s, 6H, CHMeMe), -19.0 (br s, 6H, CHMeMe), -20.4 (br s, 6H, CHMeMe), -41.3 (br s, 1H, p-H Ar), -41.7 (br s, 1H, p-H Ar), -49.3 (s, 1H, o-H Ar), -60.2(s, 1H, p-H Ar), -95.4 (s, 3H, Me(C(N))). 7 Li NMR (117 MHz, C6D6- 50pL THF-ds, 25 °C) 5 ppm 309.3 (br s).

[0398] EXEMPLE 15 : Synthèse de P15

[0399] n-BuLi (2.5 M in hexane) (1.2 mL, 1.9 mmol) was added with stirring to a solution of (£)-A-(2,6-diisopropylphenyl)-2-(((2,6-diisopropylphenyl)imino)methyl)-3-methoxyaniline (0.9 g, 1.9 mmol) in THF (9 mL) at -78 °C. The cooling bath was removed 30 min after the addition. The solution was stirred for 2 h at 25 °C. Then, FeCl (0.242 g, 1.91 mmol) was added. The solution was stirred overnight and then the solvent was evaporated under reduced pressure. The residual solid was washed with hexane and extracted with Et2O. The ethereal solution was filtered, concentrated and cooled to -20°C to give red crystals of product P15 (1.18 g, 1.58 mmol, 83%). Elemental analysis calculated for C^HssChFeLi^Ch: C, 64.44; H, 7.44; N, 3.7, found: C, 64.03; H 7.52; N 3.83. IR (cm 1): 3068, 2960, 2927, 2869, 1621, 1608, 1574, 1511, 1462, 1437, 1323, 1248, 1221, 1206, 1171, 1159, 1120, 1098, 1058, 1042, 989, 935, 913, 861, 794. (250MHz, C6D6-50 pL THF-ds, 25 °C) 5 ppm 76.8 (s, 1H, m-H Ar), 21.3 (s, 2H, m-H Ar), 13.4 (s, 2H, m-H Ar), 4.9 (br s, 8H, THF), 4.5 (s, 3H, OMe), 3.7 (s, 6H, CHMeMe), 1.9 (br s, 14H, THF, CHMeMe), -17.5 (br s, 6H, CHMeMe), -20.2 (br s, 6H, CHMeMe), -31.6 (br s, 1H, ArCHN), -34.6 (s, 1H, p-H Ar), -34.9 (s, 1H, p-H Ar), -34.6 (br s, 2H, CHMeMe), -55.8 (s, 1H, p-H Ar). 7 Li NMR (117 MHz, C6D6-50pL THF-ds, 25 °C) 5 ppm 277.7 (br s).

[0400] EXEMPLE 16 : Synthèse A de l’ester pinacolique de l’acide 1-nonylboronique

[0401] The reaction was carried out under an inert atmosphere in a glove box. A solution of bis(pinacolato)diboron (2 eq) in benzene (c = 0.5 M) was added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromononane (1 eq) in benzene (c = 0.25 M) was added to the solution, which was then made up to 0.08 M by adding benzene. The reaction mixture was stirred at 25 °C for 48 h (time not optimized) and then a saturated aqueous solution of NH4Cl was added. After extraction with EtOAc, the combined organic phases were dried over MgSCL, filtered, and evaporated under reduced pressure. Silica gel column chromatography was performed and gave 1-nonylboronic acid pinacolic ester in 25% yield. 'HNMR (300 MHz, CDCh, 22 °C) 6 ppm 1.43-1.33 (m, 2H), 1.25-1.24 (m, 22H), 0.87 (t, J = 6.4 Hz, 3H), 0.76 (t, J = 7.6 Hz, 2H). 13C{'H} NMR (75 MHz, CDCh, 22 °C) at ppm 83.0, 32.6, 32.0, 29.5, 29.4, 25.0, 24.2, 22.8, 14.3.

[0402] EXAMPLE 17: Synthesis B of 1-nonylboronic acid pinacolic ester

[0403] The reaction was carried out under an inert atmosphere in a glove box. A solution of bis(pinacolato)diboron (2 eq) in tert-amymethyl ether (c = 0.5 M) was added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromononane (1 eq) in tert-amymethyl ether (c = 0.25 M) was added to the solution, which was then made up to tert-amylmethyl ether to obtain a total bromononane concentration of 0.08 M. The reaction mixture was stirred at 25 °C for 48 h (time not optimized) 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. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave the pinacolic ester of 1-nonylboronic acid in 44% yield.

[0404] EXAMPLE 18: Synthesis C of the pinacolic ester of 1-nonylboronic acid

[0405] The reaction was carried out under an inert atmosphere in a glove box. A solution of bis(pinacolato)diboron (2 eq) in methyl tert-butyl ether (c = 0.5 M) was added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromononane (1 eq) in methyl tert-butyl ether (c = 0.25 M) was added to the solution, which was then made up to 0.08 M by adding methyl tert-butyl ether. The reaction mixture was stirred at 25 °C for 44 h (time not optimized) and then a saturated aqueous solution of NH4Cl was added. After extraction with EtOAc, the combined organic phases were dried over MgSCl, filtered, and evaporated under reduced pressure. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave 1-nonylboronic acid pinacol ester in 37% yield. NMR spectroscopic analysis gives the same result as Example 16.

[0406] EXAMPLE 19: Synthesis C of the pinacolic ester of 1-nonylboronic acid

[0407] The reaction was carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) was added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromononane (1 eq) in THF (c = 0.25 M) was added to the mixture, which was then made up to a total bromononane concentration of 0.16 M. The reaction mixture was stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered, and evaporated under reduced pressure. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave 1-nonylboronic acid pinacol ester in 49% yield. Silica gel column chromatography was performed and gave 1-nonylboronic acid pinacol ester in 35% yield.NMR spectroscopic analysis gives the same result as example 16.

[0408] EXAMPLE 20: Synthesis D of the pinacolic ester of 1-nonylboronic acid

[0409] The reaction was carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) was added to catalyst P8 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromononane (1 eq) in THF (c = 0.25 M) was added to the mixture, which was then made up to a total bromononane concentration of 0.16 M. The reaction mixture was stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl was added. After extraction with EtOAc, the combined organic phases were dried over MgSCE, filtered and evaporated under reduced pressure. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave 1-nonylboronic acid pinacol ester in 42% yield. NMR spectroscopic analysis gave the same result as Example 16.

[0410] EXAMPLE 21: Synthesis E of the pinacolic ester of 1-nonylboronic acid

[0411] The reaction was carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) was added to catalyst P7 (10 mol%) and EtNMeLi (2 eq). A solution of bromononane (1 eq) in THF (c = 0.25 M) was added to the mixture, which was then made up to a total bromononane concentration of 0.16 M. The reaction mixture was stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl was added. After extraction with EtOAc, the combined organic phases were dried over MgSO4, filtered, and evaporated under reduced pressure. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave 1-nonylboronic acid pinacol ester in 45% yield. NMR spectroscopic analysis gives the same result as Example 16.

[0412] EXAMPLE 22: Synthesis A of the pinacolic ester of cycloheptylboronic acid

[0413] The reaction was carried out under an inert atmosphere in a glove box. A solution of bis(pinacolato)diboron (2 eq) in benzene (c = 0.5 M) was added to catalyst P5 (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 made up to 0.08 M by adding benzene. The reaction mixture was stirred at 80 °C for 48 h (time not optimized) and then a saturated aqueous solution of NFLCl was added. After extraction with EtOAc, the combined organic phases were dried over MgSCL, filtered, and evaporated under reduced pressure. Silica gel column chromatography was performed and gave cycloheptylboronic acid pinacolic ester in 39% yield. 'H NMR (300 MHz, CDCL, 22 °C) δ ppm 1.78-1.68 (m, 4H), 1.57-1.54 (m, 2H), 1.49-1.43 (m, 6H), 1.23 (s, 12H). 13C{'H} NMR (75 MHz, CDCL, 22 °C) ô ppm 82.9, 29.8, 29.1, 28.5, 24.9. EXAMPLE 23: Synthesis B of the pinacolic ester of cycloheptylboronic acid

[0414] The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocycloheptane (1 eq) in THF (c = 0.25 M) is added to the mixture, which is then made up to a total bromocycloheptane concentration of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl is added. After extraction with FEtOAc, the combined organic phases are dried over MgSCL, filtered and evaporated under reduced pressure.

[0415] EXAMPLE 24: Synthesis of 2-(4-phenylbutyl)-boronic acid pinacolic ester

[0416] The reaction was carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) was added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of (3-bromobutyl)benzene (1 eq) in THF (c = 0.25 M) was added to the mixture, which was then made up to a total concentration of (3-bromobutyl)benzene of 0.16 M. The reaction mixture was stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl was added. After extraction with FEtOAc, the combined organic phases were dried over MgSCL, filtered and evaporated under reduced pressure. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave 2-(4-phenylbutyl)-boronic acid pinacolic ester in 31% yield.

[0417] EXAMPLE 25: Synthesis A of the pinacolic ester of l-(3-phenylpropyl)-boronic acid

[0418] The reaction was carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) was added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of (3-bromopropyl)benzene (1 eq) in THF (c = 0.25 M) was added to the mixture, which was then made up to a total concentration of (3-bromopropyl)benzene of 0.16 M. The reaction mixture was stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl was added. After extraction with FEtOAc, the combined organic phases were dried over MgSCL, filtered and evaporated under reduced pressure. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave l-(3-phenylpropyl)-boronic acid pinacol ester in 57% yield. Silica gel column chromatography was performed and gave l-(3-phenylpropyl)-boronic acid pinacol ester in 44% yield.'H NMR (300 MHz, CDCL, 22 °C) 5 ppm 7.29-7.24 (m, 2H), 7.19-7.13 (m, 3H), 2.61 (t, J = 7.6 Hz, 2H), 1.79-1.68 (m, 2H), s (t, J = 8.0 Hz, 2H). 13 C{'H} NMR (75 MHz, CDC13, 22 °C) at 5 ppm 142.9, 128.7, 128.3, 125.7, 83.1, 38.7, 26.2, 25.0.

[0419] AND EXAMPLE 26: Synthesis B of l-(3-phenylpropyl)-boronic acid pinacolic ester

[0420] The reaction was carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) was added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of (3-chloropropyl)benzene (1 eq) in THF (c = 0.25 M) was added to the mixture, which was then made up to a total concentration of (3-chloropropyl)benzene of 0.16 M. The reaction mixture was stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl was added. After extraction with FEtOAc, the combined organic phases were dried over MgSCl, filtered and evaporated under reduced pressure. 1 H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave the pinacolic ester of l-(3-phenylpropyl)boronic acid in 55% yield. NMR spectroscopic analysis gives the same result as Example 25.

[0421] EXAMPLE 27: Synthesis A of 2-(2-methyl-4-phenylbutyl)-boronic acid pinacolic ester

[0422] The reaction was carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) was added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of (3-methyl-3-chlorobutyl)benzene (1 eq) in THF (c = 0.25 M) was added to the mixture, which was then made up to a total concentration of (3-methyl-3-chlorobutyl)benzene of 0.16 M. The reaction mixture was stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NH4Cl was added. After extraction with FEtOAc, the combined organic phases were dried over MgSCL, filtered and evaporated under reduced pressure. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave 2-(2-methyl-4-phenylbutyl)-boronic acid pinacolic ester in 23% yield.

[0423] EXAMPLE 28: Synthesis B of the pinacolic ester of 2-(2-methyl-4-phenylbutyl)-boronic acid

[0424] The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of (3-methyl-3-chlorobutyl)benzene (1 eq) in tert-amylmethyl ether (c = 0.25 M) is added to the mixture which is then made up to a total concentration of (3-methyl-3-chlorobutyl)benzene of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NH4Cl is added. After extraction with EtOAc, the combined organic phases are dried over MgSCL, filtered and evaporated under reduced pressure.

[0425] EXAMPLE 29: Synthesis of 1-adamantylboronic acid pinacolic ester

[0426] The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromoadamantane (1 eq) in THF (c = 0.25 M) is added to the mixture which is then made up to a total concentration of 1-bromoadamantane of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) then a saturated aqueous solution of NFLCl is added. After extraction with EtOAc, the combined organic phases are dried over MgSCl, filtered and evaporated under reduced pressure.

[0427] EXAMPLE 30: Synthesis A of 4-(l-(benzyloxycarbonvDpiperidinvD-boronic acid) pinacolic ester

[0428] The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of benzyl 4-bromopiperidine-1-carboxylate (1 eq) in THF (c = 0.25 M) is added to the mixture, which is then made up to THF to obtain a total concentration of benzyl 4-bromopiperidine-1-carboxylate of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure.

[0429] EXAMPLE 31 Synthesis of the pi 3-oxetanyl-1 ester

[0430] The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol %) and EtNMeLi (1.2 eq). A solution of 3-bromooxetane (1 eq) in THF (c = 0.25 M) is added to the mixture, which is then made up to a total concentration of 3-bromooxetane of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure.

[0431] EXAMPLE 32: Synthesis of 3-(l-(tert-butoxycarbonyl)azetidinyl)-boronic acid pinacolic ester The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol %) and EtNMeLi (1.2 eq). A solution of 3 / -butyl 3-bromoazetidine-1 -carboxylate (1 eq) in THF (c = 0.25 M) is added to the mixture which is then made up to THF to obtain a total concentration of / -butyl 3-bromoazetidine-1-carboxylate of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) then a saturated aqueous solution of NFLCl is added. After extraction with EtOAc, the combined organic phases are dried over MgSCl, filtered and evaporated under reduced pressure.

[0432] EXAMPLE 33: Synthesis A of 3-(((re / 7- butyldimethylsilyDoxylpropyl-boronic acid pinacolic ester

[0433] The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol %) and EtNMeLi (1.2 eq). A solution of (4-bromobutoxy)(tert-butyl)dimethylsilane (1 eq) in THF (c = 0.25 M) is added to the mixture which is then made up to a total concentration of (4-bromobutoxy)(tert-butyl)dimethylsilane of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) then a saturated aqueous solution of NFLCl is added. After extraction with EtOAc, the combined organic phases are dried over MgSCl, filtered and evaporated under reduced pressure.

[0434] EXAMPLE 34 Synthesis A of the ester

[0435] The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of bromocyclopentane (1 eq) in THF (c = 0.25 M) is added to the mixture, which is then made up to a total bromocyclopentane concentration of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure.

[0436] EXAMPLE 35: Synthesis A of the pinacolic ester of 1-hexyl-boronic acid

[0437] The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 1-bromohexane (1 eq) in THF (c = 0.25 M) is added to the mixture, which is then made up to a total concentration of 1-bromohexane of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl is added. After extraction with EtOAc, the combined organic phases are dried over MgSO4, filtered and evaporated under reduced pressure. EXAMPLE 36: Synthesis of 2-(2,3-dihydro-1H-indenyl-boronic acid) pinacolato ester

[0438] The reaction is carried out under an inert atmosphere in a glove box. Bis(pinacolato)diboron (2 eq) is added to catalyst P5 (10 mol%) and EtNMeLi (1.2 eq). A solution of 2-bromo-2,3-dihydro-1H-indene (1 eq) in THF (c = 0.25 M) is added to the mixture, which is then made up to a total concentration of 2-bromo-2,3-dihydro-1H-indene of 0.16 M. The reaction mixture is stirred at 25 °C for 36 h (time not optimized) and then a saturated aqueous solution of NFLCl is added. After extraction with FEtOAc, the combined organic phases are dried over MgSCL, filtered and evaporated under reduced pressure.

[0439] EXAMPLE 37: Synthesis B of 4-(l-(benzyloxycarbonvDpiperidinvD-boronic acid) pinacolic ester

[0440] The reaction was carried out under an inert atmosphere in a glove box. A solution of bis(pinacolato)diboron (2 eq) in tert-amylmethyl ether (c = 0.5 M) was added to a solution of catalyst P7 (10 mol%) and NMe2Li (2 eq) in tert-amylmethyl ether (c = 0.5 M relative to NMe2Li). A solution of benzyl 4-bromopiperidine-l-carboxylate (1 eq) in tert-amylmethyl ether (c = 0.25 M) was added to the solution to obtain a total concentration of benzyl 4-bromopiperidine-l-carboxylate of 0.08 M. The reaction mixture was stirred at 60 °C for 48 h (time not optimized) and then a saturated aqueous solution of NFLCl was added. After extraction with FEtOAc, the combined organic phases were dried over MgSCl, filtered, and evaporated under reduced pressure. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave 4-(l-(benzyloxycarbonyl)piperidinyl)-boronic acid pinacolic ester in 30% yield.

[0441] EXAMPLE 38: Synthesis B of 3-((tert-butyldimethylsilyDoxylpropyl-boronic acid) pinacolic ester

[0442] The reaction was carried out under an inert atmosphere in a glove box. A solution of bis(pinacolato)diboron (2 eq) in tert-amylmethyl ether (c = 0.5 M) was added to a solution of catalyst P7 (10 mol%) and NMe2Li (2 eq) in tert-amylmethyl ether (c = 0.5 M relative to NMe2Li). A solution of (4-bromobutoxy)(tert-butyl)dimethylsilane (1 eq) in tert-amylmethyl ether (c = 0.25 M) was added to the solution to obtain a total concentration of (4-bromobutoxy)(tert-butyl)dimethylsilane of 0.08 M. The reaction mixture was stirred at 60 °C for 48 h (time not optimized) and then a saturated aqueous solution of NFLCl was added. After extraction with FEtOAc, the combined organic phases were dried over MgSCL, filtered and evaporated under reduced pressure.'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave 3-((tert-butyldimethylsilyl)oxy)propyl-boronic acid pinacol ester in 46% yield. EXAMPLE 39: Synthesis B of cyclopentyl-boronic acid pinacol ester.

[0443] The reaction was carried out under an inert atmosphere in a glove box. A solution of bis(pinacolato)diboron (2 eq) in tert-amylmethyl ether (c = 0.5 M) was added to a solution of catalyst P7 (10 mol%) and NMe2Li (2 eq) in tert-amylmethyl ether (c = 0.5 M relative to NMe2Li). A solution of bromocyclopentane (1 eq) in tert-amylmethyl ether (c = 0.25 M) was added to the solution to obtain a total bromocyclopentane concentration of 0.08 M. The reaction mixture was stirred at 60 °C for 48 h (time not optimized) and then a saturated aqueous solution of NH4Cl was added. After extraction with EtOAc, the combined organic phases were dried over MgSCl, filtered, and evaporated under reduced pressure. 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave the pinacolic ester of cyclopentylboronic acid in 53% yield.

[0444] EXAMPLE 40: Synthesis B of the pinacolic ester of l-hexyl-boronic acid

[0445] The reaction was carried out under an inert atmosphere in a glove box. A solution of bis(pinacolato)diboron (2 eq) in tert-amylmethyl ether (c = 0.5 M) was added to a solution of catalyst P7 (10 mol%) and NMe2Li (2 eq) in tert-amylmethyl ether (c = 0.5 M relative to NMe2Li). A solution of bromohexane (1 eq) in tert-amylmethyl ether (c = 0.25 M) was added to the solution to obtain a total bromohexane concentration of 0.08 M. The reaction mixture was stirred at 60 °C for 44 h (time not optimized) and then a saturated aqueous solution of NH4Cl was added. After extraction with EtOAc, the combined organic phases were dried over MgSCl, filtered, and evaporated under reduced pressure. 'H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard gave l-hexylboronic acid pinacolic ester in 38% yield.

Claims

CLAIMS 1. Use of at least one of the compounds of general formula (I) below: in which: • A is chosen from: ■ a group -X in which X is chosen from a chlorine atom a bromine atom ■ a grouping in which: M is a coordinating solvent p is chosen from 1, 2, 3, 4 or a decimal number which can vary from a value greater than 0 but less than 4 a group • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • Ri, R2, R3, Ri, Rs, FC. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B, in particular, using a diboron compound, in particular a diboronic acid ester.

2. Use, according to claim 1, □ of at least one of the compounds of general formula (la) following: d • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular an alkyl group linear or branched group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 10 carbon atoms • Ri, R2, Rs, R4, Rs, R- R7, Rs, R < and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms or □ of at least one of the compounds of general formula (Ib) following: in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • R1, R2, Rs, R4, Rs, ;, R7, Rs, Rg and R10, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CFs, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, or □ of at least one of the compounds of the following general formula (Ic): in which: • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CFs, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • Ri, R2, Rs, Ri, Rs, Rs. R7, Rs, R < and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CFs, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

3. Use, according to one of claims 1 or 2, of at least one of the compounds of general formula (Ia) below: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others. • Ri, R2, R3, Ri, Rs, Ri, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is different from R5 and / or R2 is different from R and Ri is different from Rio and / or R7 is different from Rg • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms or of the following general formula (Ia): in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others • R1, R2, R3, R4, Rs, R„. R7, Rs, Rg and R10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: ■ Ri is different from R5 and / or R2 is different from R4 and ■ ; either identical to Rio and R7 or identical to FC or ■ ; either different from Rio and / or R7 or different from Rg and ■ Ri is identical to R5 and R2 is identical to R4 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ia): in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others • Ri, R2, Rs, 4, Rs, ;, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is identical to R5 R2 is identical to R4 Ri is identical to Rio R7 is identical to FC • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ia): in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C • Ri, R2, Rs, 4, Rs, R„. R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is different from R5 and / or R2 is different from R4 and Ri is different from Rio and / or R7 is different from FC • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ia): in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C • R1, R2, R3, R4, Rs, R„. R7, Rs, Rg and R10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is different from R5 and / or R2 is different from R4 and Ri is identical to Rio and R7 is identical to FC or; is different from Rio and / or R7 is different from R, and Ri is identical to R5 and R2 is identical to R4 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms or of the following general formula (Ia): in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C • Ri, R2, R3, R4, Rs, ;, R7, s, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is identical to R5 R2 is identical to R4 Ri is identical to Rio R7 is identical to FC • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others. • Ri, R2, Rs, Ri, Rs, ;, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, on the condition that: Ri is different from R5 and / or R2 is different from R4 and Ri is different from Rio and / or R7 is different from Rg • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others • Ri, R2, R3, Ri, Rs, Ri, R7, R, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: ■ Ri is different from R5 and / or R2 is different from R and ■ ; either identical to Rio and R7 or identical to Rg or ■ ; either different from Rio and / or R7 or different from Rg and ■ Ri is identical to R5 and R2 is identical to R • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others • Ri, R2, Rs, Ri, Rs, ;, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, on the condition that: Ri is identical to R5 R2 is identical to R4 Ri is identical to Rio R7 is identical to Rg • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C • Ri, R2, Rs, Ri, Rs, Ri, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is different from R5 and / or R2 is different from R and Ri is different from Rio and / or R7 is different from Rg • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C • Ri, R2, R3, Ri, Rs, Ri, R7, R, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is different from R5 and / or R2 is different from R and Ri is identical to Rio and R7 is identical to Rg or Ri is different from Rio and / or R7 is different from Rg and Ri is identical to R5 and R2 is identical to R • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C • Ri, R2, Rs, R4, Rs, Ri, R7, R, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is identical to R5 R2 is identical to R Ri is identical to Rio R7 is identical to Rg • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ic): in which: • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others • Ri, R2, Rs, 4, Rs, R„. R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is different from R5 and / or R2 is different from R4 and Ri is different from Rio and / or R7 is different from FC • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ic): in which: • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others • R1, R2, R3, R4, Rs, R„. R7, Rs, Rg and R10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is different from R5 and / or R2 is different from R4 and Ri is identical to Rio and R7 is identical to FC or; is different from Rio and / or R7 is different from R, and Ri is identical to R5 and R2 is identical to R4 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms or of the following general formula (Ic): in which: • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, at least one of the groups B, C, D or E being different from the others • Ri, R2, Rs, 4, Rs, ;, R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is identical to R5 R2 is identical to R4 Ri is identical to Rio R7 is identical to FC • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ic): in which: • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C • Ri, R2, Rs, 4, Rs, R„. R7, Rs, Rg and Rio are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is different from R5 and / or R2 is different from R4 and Ri is different from Rio and / or R7 is different from FC • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ic): in which: • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C • R1, R2, R3, R4, Rs, R„. R7, Rs, Rg and R10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is different from R5 and / or R2 is different from R4 and Ri is identical to Rio and R7 is identical to FC or; is different from Rio and / or R7 is different from R, and Ri is identical to R5 and R2 is identical to R4 • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms or of the following general formula (Ic): in which: • B, C, D and E are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that B is identical to E and that D is identical to C • R1, R2, R3, R4, Rs, R„. R7, Rs, Rg and R10 are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms, provided that: Ri is identical to R5 R2 is identical to R4 Ri is identical to Rio R7 is identical to FC • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

4. Use, according to one of claims 1 to 3, of at least one of the compounds of general formula (Ia) following: in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D and E are fluorine atoms • Ri, R2, Rs, R4, Rs, R- R7, Rs, R < and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms or of the following general formula (Ib): in which: • X is chosen from one chlorine atom one bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D and E are fluorine atoms • Ri, R2, Rs, R4, Rs, R- R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) or of the following general formula (Ic): in which: • B, C, D and E are fluorine atoms • Ri, R2, R3, Ri, Rs, Rs. R7, Rs, R < and Rio, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom a linear or branched alkyl group of 1 to 5 carbon atom(s) as catalysts for the Miyaura borylation reaction, in particular for the creation of C(sp 3 )-B.

5. Use of the compounds of formula (I), according to one of claims 1 to 4, chosen from:

6. Use of at least one of the compounds of formulas (Ia), (Ib) or (Ic) according to one of claims 1 to 5, for the synthesis of one of the compounds of the following formula:

7. Use of at least one of the compounds of formulae (Ia), (Ib) or (Ic) according to one of claims 1 to 6 for carrying out a Miyaura borylation reaction from a in which Ri i is chosen from: a group in which q is equal to II or 2 and Ri2 represents a linear or branched alkyl group of 1 to 10 carbon atoms, in particular 1, a group with a compound of formula (S2): Z-Hal in which Z is chosen from: a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, in particular an octyl, hexyl, cycloheptyl or cyclopentyl group a 1-adamantyl group of formula optionally substituted by one or two methyl groups, a group a group a group a group and Hal is chosen from: a chlorine atom a bromine atom an iodine atom a -OTs group.

8. Process for the preparation of a compound of formula (X): in which Ri i is chosen from: a group in which q is equal to 0, 1 or 2 and Ri 2 represents a linear or branched alkyl group of 1 to 10 carbon atoms, in particular 1, and in which Ti, T2 and T3 are, identical or different, chosen from: a hydrogen atom, a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, optionally substituted by one or more phenyl groups or tert-butyldimethylsilyl ether groups, a linear ether group of 1 to 20 carbon atoms, a linear alkylamine group of 1 to 20 carbon atoms, optionally protected, in particular by a tert-butoxycarbonyl group or a carboxybenzyl group, a benzocyclopentane group, optionally Ti, T2 and T3 are linked together so as to form a polycycloalkane cycloalkane, in particular an adamantyl group, and optionally fused with a phenyl group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic ether group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic amine,provided that Ti, T2 and T3 do not simultaneously represent a hydrogen atom, comprising a step of bringing into contact a compound of Formula (XI):, (XI) with a compound of Formula (XII): in which Hal is chosen from: a chlorine atom a bromine atom an iodine atom a -OTs group, in the presence of a compound of formula (I): in which: • A is chosen from: ■ a group -X in which X is chosen from a chlorine atom a bromine atom ■ a grouping in which: M is a coordinating solvent p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 ■ a grouping • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • Ri, R2, R3, Ri, Rs, FR. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s) and a base.

9. Process for the preparation, according to claim 8, of a compound of formula (X): in which Ri i is chosen from: a group in which q is equal to 0, 1 or 2 and Ri 2 represents a linear or branched alkyl group of 1 to 10 carbon atoms, in particular 1, a group in which q and Ri 2 have the meaning defined above, and in which Ti, T2 and T3 are, identical or different, chosen from: a hydrogen atom, a linear or branched alkyl group of 1 to 20 carbon atoms or cyclic group of 3 to 12 carbon atoms, optionally substituted by one or more phenyl groups or tert-butyldimethylsilyl ether groups, a linear ether group of 1 to 20 carbon atoms, a linear alkylamine group of 1 to 20 carbon atoms, optionally protected, in particular by a tert-butoxycarbonyl group or a carboxybenzyl group, a benzocyclopentane group, optionally Ti, T2 and T3 are linked together so as to form a polycycloalkane cycloalkane, in particular an adamantyl group, and optionally fused with a phenyl group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic ether group, optionally two of Ti, T2 and T3 are linked so as to form a cyclic amine,provided that Ti, T2 and T3 do not simultaneously represent a hydrogen atom, comprising a step of bringing into contact a compound of Formula (XI):, with a compound of Formula (XII): in which Hal is chosen from: a chlorine atom a bromine atom an iodine atom a -OTs group, □ in the presence of a compound of formula (Ia): in which: • X is chosen from a chlorine atom and a bromine atom • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 10 carbon atoms • Ri, R2, R3, Ri, Rs, R„. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms or □ in the presence of a compound of formula (Ib): in which: • X is chosen from a chlorine atom and a bromine atom • M is a coordinating solvent • p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4 • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CR, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • Ri, R2, R3, Ri, Rs, FR. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atoms, or □ in the presence of a compound of formula (Ic): in which: • B, C, D, and E, identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • Ri, R2, R3, Ri, Rs, FC. R7, Rs, Rg and Rio, which may be identical or different, are chosen from: a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxyl group of 1 to 10 carbon atoms or a linear or branched dialkylamino group of 2 to 20 carbon atoms • G is chosen from a hydrogen atom, a linear or branched alkyl group of 1 to 5 carbon atom(s), and a base.

10. Preparation process, according to one of claims 8 or 9, □ in which said base is a lithium amide, in particular chosen from LiNMeEt, LiNMe2, LiNEt2, LiN(iPr)2, LiNTMS2, LiNPhMe, in particular LiNMeEt or LiNMe2, in particular LiNMeEt. or □ wherein said process is carried out in solution in a non-coordinating apolar solvent, in particular chosen from benzene, hexane, toluene, cyclohexane or methylcyclohexane. or □ wherein said process is carried out in solution in a coordinating solvent selected from diethyl ether, dimethoxymethane, dimethoxyethane, diethoxymethane, tetrahydrofuran, tert-butylmethylether, tert-butylethylether, methyl tetrahydrofuran, tert-amylmethyl ether or 1,4-dioxane, in particular selected from tetrahydrofuran, tert-butylmethylether or tert-amylmethyl ether. or □ wherein said base is LiNMeEt and said process is carried out in solution in tert-amylmethyl ether. or □ wherein said base is LiNMeEt and said process is carried out in solution in tetrahydrofuran, or □ wherein said base is LiNMe2 and said process is carried out in solution in tert-amylmethyl ether.

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