Method for preparing trifluorovinylamines

Abstract

The present invention relates to a method for preparing a trifluorovinylamine (II) by reacting the molecule (I) with an amine compound in one or two steps: the method implementing the reaction of the compound of formula (I) with the compound of formula (V): or the reaction with the compound of formula (III); to form the compound of formula (IV) which reacts with the compound of formula (V), wherein the groups R1 and R2 together form a heterocycle or independently represent a functional group selected from among a hydrogen and an aliphatic chain selected from among C1-12alkyl, C1-12heteroalkyl, C6-10aryl and C4-10heteroaryl, optionally comprising one or more substituents selected from among -F; -Cl; -Br; -I; -NO2; -CN; - CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-; -C(=O)O-; -C(=O)S- and -C(=O)N- where X is a halogen.

Description

[0001] PROCESS FOR PREPARING TRIFLUOROVINYLAMINESThe present invention is in the field of the chemistry of fluorinated organic compounds and relates more particularly to the valorization of small-sized polyfluorinated carbon molecules, typically those containing less than three, or even less than two, carbon atoms, for the synthesis of larger compounds. State of the art Fluoroform, of formula CHF3, is a by-product of the polymer industry and produced on a scale that is particularly harmful to the environment and whose thermal destruction requires quantities of energy that are far too high to be part of a sustainable development approach.There is a growing need for the valorization of this fluoroform, or its difluorinated analogues CHF2Br and CHF2I, which are currently considered more as industrial waste, in order to transform them into products usable in the fields of pharmaceuticals, cosmetics, agrochemicals, etc. Fluorinated compounds represent 20% of all drugs placed on the market, and more than 40% of all agrochemicals recently placed on the market. Many of these compounds, especially those with -CF2- and CF3- groups, are currently produced from simpler fluorinated building blocks containing 2 or more carbon atoms. For example, the major difluorinated C2 building blocks include ethyl difluoroacetate, which is produced from tetrafluoroethylene (TFE), and ethyl bromodifluoroacetate, which is ultimately derived from restricted C2 halofluorocarbons such as 1,1,2-trichloro-1,2,2-trifluoroethane.The industrial production of TFE and related (halo)fluorocarbon compounds relies on the dimerization of CHF2Cl, the synthesis of which is accompanied by the generation of fluoroform (CHF3, HFC-23), a by-product with extremely high global warming potential. Given the environmental concerns of CHF3, its recycling into synthetically useful C2 fluorinated building blocks appears to be a promising avenue, as it makes the fluorochemical value chain more efficient by directly utilizing CHF3 and reducing the demand for C2 polyhalogenated derivatives that are associated with an additional CHF3 burden (in the case of TFE) and / or ozone depletion potential (in the case of halofluorocarbon compounds).Known examples of direct conversion of CHF3 to fine chemicals include (see Scheme 1):- generation and nucleophilic addition of transient CF3- anions (Scheme 1a) (see Saito, T., et al., 'Direct Nucleophilic Trifluoromethylation of Carbonyl Compounds by Potent Greenhouse Gas, Fluoroform: Improving the Reactivity of Anionoid Trifluoromethyl Species in Glymes', published in Scientific Reports, vol. 8, no. 1, July 2018, p. 11501.);- direct cupration of CHF3 leading to a potent trifluoromethylating reagent [CuCF3] (Scheme 1b) (see Zanardi, A., Novikov, M.A., Martin, E., Benet-Buchholz, J. & Grushin, V.V. Direct Cupration of Fluoroform. Published in J.Am. Chem. Soc. 133, 20901–20913 (2011). ;- the synthesis of a widely used TMSCF3 reagent (Scheme 1c) (see the publication by Prakash, GKS, Jog, PV, Batamack, PTD & Olah, GAentitled “Taming of Fluoroform: Direct Nucleophilic Trifluoromethylation of Si, B, S, and C Centers” published in Science 338, 1324–1327 (2012).] ;- difluorocarbene-mediated difluoromethylation of anionic nucleophilic species to C / O or S (Scheme 1d) (see the publication by M. Köckinger et al. entitled “Scalable Continuous Flow Process for the Synthesis of Eflornithine Using Fluoroform as Difluoromethyl Source” published in the journal Org. Process Res. Dev. 22, 1553–1563 (2018). ;- the synthesis of a reagent CF3SO3H (see the publication by Mukhopadhyay, S., Bell, A.T., Srinivas, R.V. & Smith, G.S. entitled “Synthesis of Trifluoromethanesulfonic Acid from CHF 3”. published in Org. Process Res. Dev. 8, 660–662 (2004). ;- the synthesis of a CF3Br reagent (see the publication by Skapin, T., et al. entitled 'Synthesis of Halogenated Methanes'” published in . Journal of Fluorine Chemistry, vol.45, no.1, Oct.1989, p.163.]. Scheme 1. Furthermore, the publication of Doklady Akademii Nauk SSSR, vol 161(6), page 1362 to 1364 describes the synthesis of N-fluorovinyl derivatives which consists in reacting a lithium or potassium amide substituted in position 1 by an alkyl or aryl group - 1 derived from diethylamine, piperidine, morpholine, methylaniline and carbazole with fluoroolefins such as tetrafluoroethylene, chlorotrifluoroethylene, trifluoroethylene, vinylidene fluoride and hexafluoropropene in media such as ether, tetrahydrofuran or dioxane. The chemical abstract entitled "Reaction of direct fluoroalkenylation. I. Synthesis oftrifluorovinyl and chlorodifluorovinylamines” (accession number: 1966:490544 HCAPLUS full text) describes the reaction of perfluorovinyl with a lithium amide which corresponds to the amine group of the final product. JP S6322546 A describes the decarboxylation of the amino and fluorinated propionic acid,which results in the following compound: Me2 N-CF=CF2.None of these documents uses as starting reagent a compound chosen from CHF3 and CHF2Cl. Technical problem The present invention aims to offer a new approach to the valorization of CHF3, and more generally compounds of formula CHF2X, X being a halogen. Unlike the processes of the prior art shown in Scheme 1 using CHF3, the process according to the present invention aims to obtain a more versatile C2 reagent, typically trifluorovinylamine (TFVA), which can be used as a synthon for the synthesis of known or new fluorinated chemicals.Definitions Within the scope of the invention, the compounds described may be substituted by any number of substituents or functional groups. In general, the term "substituted", whether or not preceded by the term "optionally", and the substituents contained in the formulas of the present invention,refer to the replacement of hydrogen radicals in a given structure with the radical of a specified substituent. When more than one position in a given structure may be substituted with more than one substituent selected from a specified group, the substituent may be either the same or different at each position. As used herein, the term "substituted" encompasses all permitted substituents for organic compounds. Generally speaking, permitted substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and non-aromatic, carbon and heteroatom substituents of organic compounds. For the purposes of the present invention, heteroatoms such as nitrogen may have hydrogen substituents and / or any permitted substituent of the organic compounds described herein that satisfy the valences of the heteroatoms. In addition,The present invention is not intended to be limited in any way by the permitted substituents of the organic compounds. The combinations of substituents and variables contemplated by the present invention are preferably those that result in the formation of stable compounds useful in the treatment and prevention of disorders, or for a particular use. Examples of substituents include, but are not limited to, the following: aliphatic; heteroaliphatic; alicyclic; heteroalicyclic; aromatic, heteroaromatic; aryl; heteroaryl; alkylaryl; alkylheteroaryl; alkoxy; aryloxy; heteroalkoxy; heteroaryloxy; alkylthio; arylthio; heteroalkylthio; heteroarylthio; F; Cl; Br; I; -NO2; -CN; -CF3; -CH2CF3; -CHC12; -CH2OH; -CH2CH2OH; -CH2NH2; -CH2SO2CH3 and / or -GRG1 in which G is - O-, -S-, -NRG2-, -C(=O)-, -S(=O)-, -SO2-, -C(=O)O-, -C(=O)NRG2-, -OC(=O)-, - NRG2C(=O)-, -OC(=O)O-, -OC(=O)NRG2-, -NRG2C(=O)O-,-NRG2C(=O)NRG2-, - C(=S)-, -C(=S)S-, -SC(=S)-, -SC(=S)S-, -C(=NRG2)-, -C(=NRG2)O-, - C(=NRG2)NRG3-, -OC(=NRG2)-, -NRG2C(=NRG3)-, -NRG2SO2-, -NRG2SO2NRG3-, or -SO2NRG2-, wherein each occurrence of RG1, RG2, and RG3 independently comprises, but is not limited to, hydrogen, halogen, or an optionally substituted aliphatic, heteroaliphatic, alicyclic, heteroalicyclic, aromatic, heteroaromatic, aryl, heteroaryl, alkylaryl, or alkylheteroaryl group. Other examples of generally applicable substituents are illustrated by the specific embodiments shown in the examples described in the remainder of the specification. The term "stable," as used herein, preferably refers to compounds that possess sufficient stability to permit manufacture and that retain the integrity of the compound for a period sufficient to be detected and, preferably,for a period of time sufficient to be useful for the purposes described herein. The term "stability" may refer to the ability to resist degradation, to persist in a given environment, and / or to retain a particular structure. The term "aliphatic," as used herein, includes saturated and unsaturated aliphatic hydrocarbons, straight (i.e., unbranched) or branched, which are optionally substituted with one or more functional groups. As will be appreciated by those of ordinary skill in the art, the term "aliphatic" herein includes, but is not limited to, alkyl, alkenyl, and alkynyl groups. Thus, as used herein, the term "alkyl" includes straight and branched alkyl groups. A similar convention applies to other generic terms such as "alkenyl," "alkynyl," etc. In addition, as used herein, the terms "alkyl," "alkenyl,""Alkynyl" and the like encompass both substituted and unsubstituted groups. The term "alkyl" also includes the term "cycloalkyl". The term "cycloalkyl", as used herein, includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and the like, which, as in the case of aliphatic, heteroaliphatic or heterocyclic groups, may be optionally substituted. A similar convention applies to other generic terms such as "cycloalkenyl", "cycloalkynyl", etc. Illustrative aliphatic groups for straight and branched alkyl groups include, but are not limited to, for example, methyl, ethyl, n-propyl, isopropyl, allyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, tert-pentyl, n-hexyl, sec-hexyl, groups and the like, which, again,may bear one or more substituents. Alkenyl groups include, but are not limited to, for example, ethenyl, propenyl, butenyl, 1-methyl-2-buten-1-yl, etc. Representative alkyne groups include, but are not limited to, ethynyl, 2-propynyl (propargyl), 1-propynyl, and other similar groups. The term "alicyclic," as used herein, refers to compounds that combine the properties of both aliphatic and cyclic compounds and includes, but is not limited to, cyclic or polycyclic aliphatic hydrocarbons and bridged cycloalkyl compounds, which are optionally substituted with one or more functional groups. As will be appreciated by any person of ordinary skill in the art, the term "alicyclic" is herein understood to include, but is not limited to, cycloalkyl, cycloalkenyl and cycloalkynyl groups,which are optionally substituted with one or more functional groups. Illustrative alicyclic groups therefore include, but are not limited to, for example, cyclopropyl, -CH2-cyclopropyl, cyclobutyl, -CH2-cyclobutyl, cyclopentyl, -CH2-cyclopentyl-n, cyclohexyl, - CH2-cyclohexyl, cyclohexenylethyl, cyclohexanylethyl, norborbyl groups and the like, which, again, may carry one or more substituents. The term "heteroaliphatic" refers to aliphatic groups in which one or more carbon atoms in the main chain have been replaced by a heteroatom. Thus, a heteroaliphatic group refers to an aliphatic chain which contains one or more oxygen, sulfur, nitrogen, phosphorus or silicon atoms, i.e., in place of the carbon atoms. The terms "heteroalicyclic","heterocycloalkyl" or "heterocyclic" means compounds that combine the properties of heteroaliphatic and cyclic compounds and include, but are not limited to, saturated and unsaturated mono- or polycyclic heterocycles such as morpholino, pyrrolidinyl, furanyl, thiofuranyl, pyrrolyl, etc. which are optionally substituted with one or more functional groups, as defined herein. In some instances, the term "heterocyclic" means a non-aromatic 5-, 6-, or 7-membered ring or polycyclic group, including, but not limited to, a bi- or tricyclic group comprising fused six-membered rings having between one and three heteroatoms independently selected from oxygen, sulfur, and nitrogen, wherein (i) each 5-membered ring has 0 to 2 double bonds and each 6-membered ring has 0 to 2 double bonds, (ii) the nitrogen and sulfur heteroatoms may optionally be oxidized,(iii) the nitrogen heteroatom may optionally be quaternized, and (iv) any of the above heterocyclic rings may be fused to an aryl or heteroaryl ring. Representative heterocycles include, but are not limited to, pyrrolidinyl, pyrazolinyl, pyrazolidiny1, imidazolinyl, imidazolidinyl, piperidinyl, piperazinyl, oxazolidiny1, isoxazolidinyl, morpholinyl, thiazolidinyl, isothiazolidinyl, and tetrahydrofuryl. The term "aromatic moiety," as used herein, refers to stable, unsaturated, substituted or unsubstituted mono- or polycyclic hydrocarbon moieties, preferably having from 3 to 14 carbon atoms, comprising at least one ring satisfying Huckel's rule for aromaticity. Examples of aromatic units include, but are not limited to, phenyl, indanyl, indenyl, naphthyl, phenanthryl, and anthracyl. The term "heteroaromatic moiety," as used herein,denotes stable, unsaturated, substituted or unsubstituted monoheterocyclic or polyheterocyclic groups, preferably having from 3 to 14 carbon atoms, comprising at least one ring satisfying Huckel's rule with respect to aromaticity. Examples of heteroaromatic groups include, but are not limited to, pyridyl, quinolinyl, dihydroquinolinyl, isoquinolinyl, quinazolinyl, dihydroquinazolyl and tetrahydroquinazolyl. Aromatic and heteroaromatic groups, as defined herein, may be attached by an aliphatic (e.g., alkyl) or heteroaliphatic (e.g., heteroalkyl) group and thus also include groups such as -(aliphatic)aromatic, -(heteroaliphatic)aromatic, -(aliphatic)heteroaromatic, -(heteroaliphatic)heteroaromatic, -(alkyl)aromatic,-(heteroalkyl)aromatic, -(alkyl)heteroaromatic, and -(heteroalkyl)heteroaromatic. Thus, in this document, the terms "aromatic or heteroaromatic groups" and "aromatic, heteroaromatic, -(alkyl)aromatic, -(heteroalkyl)aromatic, -(heteroalkyl)heteroaromatic, and -(heteroalkyl)heteroaromatic" are interchangeable. Substituents include, but are not limited to, all of the previously mentioned substituents that result in the formation of a stable compound. The term "aryl" refers to aromatic groups. In certain embodiments of the present invention, the term "aryl" refers to a mono- or bicyclic carbocyclic ring system having one or two rings satisfying Huckel's rule for aromaticity, including, but not limited to, phenyl, naphthyl, tetrahydronaphthyl, indanyl, indenyl, and the like. Similarly,the term "heteroaryl" refers to heteroaromatic groups. In certain embodiments of the present invention, the term "heteroaryl", as used herein, refers to an unsaturated cyclic radical having one ring atom selected from S, O and N; the ring may include zero, one or two additional heteroatoms independently selected from S, O and N; and the remaining ring atoms are carbon atoms, the radical being connected to the remainder of the molecule through any of the ring atoms, forming a radical, for example, pyridyl, pyrazinyl, pyrimidinyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isooxazolyl, thiadiazolyl, oxadiazolyl, thiophenyl, furanyl, quinolinyl, isoquinolinyl, etc. Substituents for aryl and heteroaryl units include, but are not limited to, all of the previously mentioned substituents, i.e., the substituents cited for aliphatic units,or for other reasons for the formation of a stable compound. In some cases, the aliphatic group contains 1 to 12 aliphatic carbon atoms. In other cases, the aliphatic group contains 6 to 10 aliphatic carbon atoms. In still other embodiments, the aliphatic group contains 4 to 10 aliphatic carbon atoms. For example, the term "C1-12alkyl" defines an alkyl of 1 to 12 carbon atoms; the same terminology being applicable for a "C2-12alkenyl" which relates to an alkenyl of 2 to 12 carbon atoms, which can be extended to other aliphatics such as alkynyls, heteroalkyls, etc. The terms "alkoxy" (or "alkyloxy") and "thioalkyl" mean an alkyl group, as defined above, attached to the parent molecular moiety through an oxygen atom ("alkoxy") or through a sulfur atom ("thioalkyl"). Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy,tert-butoxy, neopentoxy, and n-hexoxy. Examples of thioalkyl groups include, but are not limited to, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, etc. The term "hydroxyl," as used herein, refers to a group having the structure -OH, and the term "hydroxyl protecting group," as used herein, unless otherwise indicated, refers to a substituent that is generally used to block or protect a hydroxyl on the compound, thereby protecting its functionality while allowing the reaction of other functional groups on the compound. Non-exclusive examples of a hydroxyl protecting group include: acyl groups (e.g., formyl, acetyl, chloroacetyl, trichloroacetyl, O-nitrophenylacetyl, O-nitrophenoxyacetyl, trifluoroacetyl, acetoacetyl, 4-chlorobutyryl, isobutyryl, O-nitrocinnamoyl, picolinoyl, acylisothiocyanate, aminocaproyl, benzoyl, and the like),acyloxy groups (e.g., 1-tert-butyloxycarbonyl (Boc), methoxycarbonyl, 9-fluorenyl-methoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-trimethylsilylethoycarbonyl, vinyloxycarbonyl, allyloxycarbonyl, 1,1-dimethyl-propynyloxycarbonyl, benzyloxy-carbonyl, p-nitrobenzyloxycarbony, 2,4-dichlorobenzyloxycarbonyl, etc.), diphenylmethane, silyl ether (e.g., tert-butyldimethylsilyl ether, abbreviated as "TBS") and benzylcarbamates. "Hydroxyl deprotection" as used herein refers to the chemical reaction involving a deprotecting agent to remove the substituent that had previously been used to protect the hydroxyl. The term "amine" means a group having the structure -N(R)2 in which each occurrence of R is independently hydrogen or an aliphatic, heteroaliphatic, aromatic or heteroaromatic group, or the R groups, taken together,may form a heterocyclic group. The term "alkylamino" means a group having the structure -NHR' in which R' is alkyl, as defined herein. The term "aminoalkyl" means a group having the structure NH2R'-, where R' is alkyl, as defined herein. In some instances, the alkyl group contains about 1 to 20 aliphatic carbon atoms. In other instances, the alkyl group contains about 1 to 10 aliphatic carbon atoms. In still other instances, the alkyl, alkenyl, and alkynyl groups used herein contain about 1 to 8 aliphatic carbon atoms. In still other embodiments, the alkyl group contains about 1 to 6 aliphatic carbon atoms. In still other embodiments, the alkyl group contains about 1 to 4 aliphatic carbon atoms. Examples of alkylamino include, but are not limited to, methylamino, ethylamino, iso-propylamino, and others. The "amine protecting group",as used herein, unless otherwise indicated, refers to a substituent that is generally used to block or protect an amine on the compound, thereby protecting its functionality while allowing the reaction of other functional groups on the compound. Non-exclusive examples of amine protecting groups include: acyl groups (e.g., formyl, acetyl, chloroacetyl, trichloroacetyl, O-nitrophenylacetyl, O-nitrophenoxyacetyl, trifluoroacetyl, acetoacetyl, 4-chlorobutyryl, isobutyryl, O-nitrocinnamoyl, picolinoyl, acylisothiocyanate, aminocaproyl, benzoyl, and the like), acyloxy groups (e.g., 1-tert-butyloxycarbonyl (Boc), methoxycarbonyl, 9-fluorenylmethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-trimethylsilylethoycarbonyl, vinyloxycarbonyl, allyloxycarbonyl, 1,1-dimethylpropynyloxycarbonyl, benzyloxycarbonyl, p-nitrobenzyloxycarbonyl, 2,4-dichlorobenzyloxycarbonyl, and the like),diphenylmethane and benzylcarbamates. The terms "halo" and "halogen" as used herein refer to an atom selected from fluorine, chlorine, bromine, and iodine. The term "halogenated" refers to a portion of a molecule to which one, two, or three halogen atoms are attached. The term "haloalkyl" refers to an alkyl group, as defined above, to which one, two, or three halogen atoms are attached and is exemplified by groups such as chloromethyl, bromoethyl, trifluoromethyl, etc. The term "acyloxy," as used herein, does not differ materially from the common meaning of that term in the art, and refers to a moiety of the structure - OC(O)RX, wherein RX is a substituted or unsubstituted aliphatic, alicyclic, heteroaliphatic, heteroalicyclic, aryl, or heteroaryl moiety. The term "acyl" as used herein does not differ substantially from the common meaning of that term in the art,and refers to a moiety of structure - C(O)RX, wherein RX is a substituted or unsubstituted, aliphatic, alicyclic, heteroaliphatic, heteroalicyclic, aryl, or heteroaryl moiety. The term "imino," as used herein, does not differ materially from the common meaning of that term in the art and refers to a group of structure -C(=NRX)RY, wherein RX is hydrogen or an optionally substituted aliphatic, alicyclic, heteroaliphatic, heteroalicyclic, aryl, or heteroaryl group, and RY is an optionally substituted aliphatic, alicyclic, heteroaliphatic, heteroalicyclic, aryl, or heteroaryl group. Unless otherwise indicated, the term "sulfonate leaving group," as used herein, refers to anions having the general formula RSO2O-. Non-limiting examples of sulfonate leaving group include: mesylate (R=CH3), triflate (R=CF3), tosylate (R=CH3C6H4,abbreviated as "Ts") such as para-tosylate (p-Ts).In this specification, the terms "aliphatic", "heteroaliphatic", "alkyl", "alkenyl", "alkynyl", "heteroalkyl", "heteroalkenyl", "heteroalkynyl" and the like, encompass substituted and unsubstituted, saturated and unsaturated, straight and branched groups. Similarly, the terms "alicyclic", "heterocyclic", "heterocycloalkyl", "heterocycle" and the like encompass substituted and unsubstituted, saturated and unsaturated groups. Furthermore, the terms "cycloalkyl", "cycloalkenyl", "cycloalkynyl", "heterocycloalkyl", "heterocycloalkenyl", "heterocycloalkynyl", "aromatic", "heteroaromatic", "aryl", "heteroaryl" and other similar terms, whether used alone or as part of a larger moiety, encompass both substituted and unsubstituted groups. Description of the Invention The present invention seeks to overcome the above-mentioned disadvantages,by implementing an alternative process for the preparation of a synthesis intermediate suitable for a wide variety of uses in total synthesis. To this end, the present invention relates to a process for the preparation of a trifluorovinylamine of formula (II) using a molecule of formula (I) in n steps, n being equal to 1 or 2, :, in which the groups R1 and R2 together form a heterocycle or independently represent a functional group chosen from a hydrogen and an aliphatic chain chosen from at least one of the following chains: a linear, branched, cyclic, substituted and unsubstituted chain; the aliphatic chain being chosen from a C1-12alkyl, C1-12heteroalkyl, C6-10aryl and C4- 10heteroaryl, ; each of the alkyl, heteroalkyl, aryl and heteroaryl groups defined above optionally comprising one or more substituents comprising at least one atom or function chosen from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-; -C(=O)O-; -C(=O)S- and -C(=O)N-; and R1 and R2 preferably represent a branched or cyclic alkyl chain; and in which X is a halogen preferably chosen from -F and -Cl, said process implementing the reaction of the compound of formula (I) with the compound of formula (V) following: or the reaction of the compound of formula (I) with the compound of the following formula (III); to form the compound of the following formula (IV): which reacts with the compound of formula (V) to form the compound of formula (II), all the reactions are preferably carried out in a solvent comprising THF, and the metal M is preferably selected from Li and Na. The number of steps carried out in the process according to the invention is n, being an integer greater than or equal to 1; and n is taken to be less than 5. Preferably n is less than 4, and advantageously n is less than 3 or from 1 to 2. Preferably, the halogen of group X of the compound of formula (I) is fluorine -F, the compound (I) then being a fluoroform molecule. The inventors discovered completely unexpectedly that the compound (II), despite its significant steric hindrance, could be prepared from fluoroform or one of its halogenated derivatives.According to one embodiment, the process for preparing a trifluorovinylamine of formula (II) comprises a step of transforming the fluoroform (Ia) to give an intermediate product Me3SiCF3(IV) according to the following synthesis route:. , such a synthesis route is advantageously composed of two steps making it possible to limit the reaction sequence to reach the targeted molecule. Preferably, steps 1- and 2- are carried out in a solvent comprising THF, or even which is exclusively composed of it; and the metal M of the alkyl amide of formula (V) is preferably an alkali metal, which metal is advantageously a metal selected from Li and Na. According to another embodiment, the process for preparing a trifluorovinylamine of formula (II) according to the present invention comprises the following synthesis route: such a synthesis route is advantageously composed of a single step allowing the targeted molecule to be directly reached. The synthesis of trifluorovinylamine of formula (II) in a single step, according to the synthesis route presented previously in the context of the invention, uses the compound of formula (V) comprising the metal M which is preferably an alkali metal, advantageously selected from Li and Na; and the reaction solvent advantageously comprises THF, or is even composed of THF. To improve the reaction conditions, in particular to improve the yield, the THF may be wholly or partly substituted by other suitable solvents, such as hexane and / or diethyl ether. Preferably, the preparation process according to the present invention more particularly results in the following compounds of formula (IIa-IIb): Preferably, the compounds (V) which can be used for the synthesis of trifluorovinylamine of formula (II) correspond to the formulas below and are lithium amides: These lithium amides are known and described in particular in the work entitled "Metal Amide Chemistry" by M. Lappert, A. Protchenko, P. Power and A. Seeber, published by Wiley, New York in 2008 (see page 7, in particular). The synthesis routes implementing the one- or two-step process described previously in the context of the present invention, more advantageously make it possible to obtain all the targeted compounds of formula (II) starting from the lithium amides of alkyls of formula (V) for example derived from dicyclohexylamine, 2,2,6,6 tetramethylpiperidine, dimethylamine, diethylamine, diisopropylamine, N-methylaniline, carbazole or 2-pyrolidine. The present invention also relates to new synthesis routes implementing at least one of the compounds of formula (II) presented above in the context of the invention, and comprising the following steps: R3 being a functional group selected from a hydrogen and an aliphatic chain selected from at least one of the following chains: a linear, branched, cyclic, substituted and unsubstituted chain; the aliphatic chain being selected from a C1-12alkyl, C1-12heteroalkyl, C6-10aryl and C4-10heteroaryl group; each of said alkyl, heteroalkyl, aryl and heteroaryl groups optionally comprising one or more substituents comprising at least one atom or function selected from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO3-; -SO2; -C(=O)O-; -C(=O)S- and -C(=O)N-; Q representing a functional group selected from hydrogen and a substituent comprising an element having an electronegativity lower than that of carbon, in particular a metal M', M' preferably being selected from Mg and Li. The electronegativity is the Pauling electronegativity; carbon having an electronegativity of 2.55.Preferably, the above-mentioned method for synthesizing a compound according to formula (VI) comprising said m synthesis steps, implements the method for preparing the compound of formula (II) presented previously within the framework of the invention. The number of steps implemented in the method for synthesizing (VI) according to the invention is m, m being an integer greater than or equal to 1; and m is taken less than 5. Preferably m is taken less than 4 or from 1 to 3. Preferably, the method for synthesizing a compound of formula (VI) according to the invention targets the synthesis of a compound of formula (VI.1):. in which the substituent Ar 1 is selected from the C groups 6-10 aryl and C 4-10heteroaryl; each of the aryl and heteroaryl groups defined above for the compound (VI.1) optionally comprising one or more substituents comprising at least one atom or function chosen from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-; -C(=O)O-; -C(=O)S- and -C(=O)N-; andpreferably, the compound (VI.1) is selected from the following compounds (VIa-VIh):

[0002] The present invention also relates to new synthesis routes using at least one of the compounds of formula (II) presented above in the context of the invention, and comprising the following steps: R5 and R6 independently representing a functional group chosen from a hydrogen and an aliphatic chain chosen from at least one of the following chains: a linear, branched, cyclic, substituted or unsubstituted chain; the aliphatic chain being chosen from a C1-12alkyl, C1-12heteroalkyl, C 6-10aryl andC4-10heteroaryl; each of said alkyl, heteroalkyl, aryl and heteroaryl groups optionally comprising one or more substituents comprising at least one atom or a function chosen from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-;; -C(=O)O-; -C(=O)S- and -C(=O)N-.Preferably, the above-mentioned process for the synthesis of a compound according to formula (VIII) comprising said q synthesis steps, implements the process for the preparation of the compound of formula (II) presented previously within the scope of the invention. The number of steps implemented in the process for the synthesis of (VIII) according to the invention is q, q being an integer greater than or equal to 1; and p is taken less than 5. Preferably, p is taken less than 4 or from 1 to 3. Preferably, the method for synthesizing a compound of formula (VIII) according to the invention targets the synthesis of a compound of formula (VIIIa-VIIId): The present invention also relates to new synthetic routes using at least one of the compounds of formula (II) presented above in the context of the invention, and comprising a reaction step between the compound (II) and a disubstituted orthoaromatic, or even a disubstituted ortho heteroaromatic, such that one of the substituents of the aromatic or heteroaromatic comprises an atom of -N- and the other an atom of -O-, -N-, -S- and / or -Se-; preferably said synthetic routes comprise the following step and use the following arene: Preferably, the above-mentioned method for synthesizing a compound according to formula (IX) uses the method for preparing the compound of formula (II) presented above in the context of the invention.The present invention also relates to new synthetic routes using at least one of the compounds of formula (II) presented above in the context of the invention, according to the following reaction: , the methyl groups on the nitrogen of the compound which reacts with TFVA can optionally, independently of one another, be replaced by other substituents such as an ether group, for example MeO-, an ester group, etc. The present invention relates, according to another aspect, to a compound obtained, or capable of being obtained, from fluoroform of formula (I) according to the process for preparing the compound of formula (II) described in the context of the present invention, said compound being represented by the following general formula (IIc): wherein the groups R7, R8, R11, and R12 independently represent a functional group selected from hydrogen and an aliphatic chain selected from at least one of the following chains: a linear, branched, cyclic, substituted and unsubstituted chain; the aliphatic chain being selected from a C1-12alkyl, C1-12heteroalkyl, C6-10aryl and C4-10heteroaryl group; each of said alkyl, heteroalkyl, aryl and heteroaryl groups optionally comprising one or more substituents comprising at least one atom or function selected from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-; -C(=O)O-; -C(=O)S- and -C(=O)N-; the groups R9 and R 10 :- taken independently, represent a functional group as defined for the groups R7, R8, R11, and R12; and- taken together, represent a single cyclic aliphatic chain comprising the C atoms carrying the groups R9 and R 10and the N atom carrying said C atoms carrying R9 and R10; the cyclic aliphatic chain being chosen from a C1-12alkyl, C1-12heteroalkyl group, each of said alkyl, heteroalkyl groups defined above optionally comprising one or more substituents comprising at least one atom or function chosen from -F; -Cl; -Br; -I; -NO2; -CN; - CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-; -C(=O)O-; -C(=O)S- and -C(=O)N-; excluding compounds (IId-IIf), in which the groups R7, R8, R11, and R12 are chosen from four hydrogens and the groups R9 and R 10 are included in the nitrogen cycles identified in (IId-IIf): Preferably, the compound of formula (IIc) according to the invention is selected from the following compounds (IIa-IIb): The compounds of formula (II) allow one-step synthesis protocols for compounds comprising the CF2 motif, protocols which are usually carried out in two or more steps. The compounds of formula II exhibit a unique reactivity for fluorinated compounds in the presence of Lewis acid. In general, the compounds of formula II can interact with nucleophiles in the presence of Lewis acids to generate difluoroenamine-type species, observable by NMR and often isolatable, species which can then be functionalized. Furthermore, the compounds of formula (II) allow the synthesis of new compounds such as the compounds of formula (VIe), (VIIIa) and (VIIIc) mentioned above. The present invention is also described in the detailed description which follows, using the experimental part which details certain embodiments using examples, given solely for illustrative purposes and which should not be considered as limiting.Experimental Part Experimental Materials and ProtocolsAll reactions were performed using oven-dried glassware and magnetic stirring under argon unless otherwise stated. Reaction temperatures are reported as the bath temperature surrounding the vessel. Analytical thin-layer chromatography was performed on aluminum silica gel plates with F-254 indicator and visualized by UV light (254 nm) and / or chemical staining with KMnO4 solution or ninhydrin solution. Flash column chromatography was performed using 0.040-0.063 nm silica gel. 1H NMR spectra were recorded on a BrukerDXP 300 MHz spectrometer at 300.1 MHz, NMR spectra. 13 C at 75.5 MHz, the NMR spectra 1 9 F at 282.4 MHz. Chemical shifts (δ) are indicated in ppm relative to TMS ( 1 H) and CFCl3( 19F). Coupling constants (J) are expressed in Hz. The following abbreviations were used to indicate multiplicities: s: singlet, d: doublet, t: triplet, q: quadruplet, dd: doublet of doublet, ddd: doublet of doublet of doublet, dt: doublet of triplet, m: multiplet. Signals from residual solvents were used as references (CDCl3: δH = 7.26 ppm, δC = 77.16 ppm; (CD3)2SO: δH = 2.50 ppm, δC = 39.52 ppm or relative to external CFCl3, δF = 0 ppm). High-resolution mass spectrometry (HRMS) was performed on an electrospray ionization mass spectrometer with a micro-TOF analyzer. Infrared spectra were recorded on a Perkin Elmer Paragon 100 FT-IR spectrometer (ATR), wavenumbers (^) of the recorded IR signals (ATR) are indicated in cm- 1. Melting points were measured on a STUART SMP3 apparatus in open capillaries. 30 Examples Part 1: Preparation of dicyclohexyl(trifluorovinyl)amine of formula IIb Two solutions are prepared:- Solution A: 300 mL of CHF30.3M in THF, prepared by saturating THF with CHF3 at 0°C and ambient pressure, followed by stirring at 20°C for 2 h.- Solution B: 300 mL of 0.5M Cy2NLi (Va), prepared by adding 60 mL of 2.5M n-BuLi solution in hexane to a solution of 30 mL of dicyclohexylamine in 210 mL of THF. Both solutions A and B are pumped (Syrris ASIA™ pump) at 5 mL / min each into a flow apparatus (ID 1.6 mm) consisting of two 2 mL pre-cooling tubes followed by a T-mixer and a 1 mL reactor tube. The entire setup is immersed in an ice-water bath. The reactor outlet is inserted into a 1L flask (under argon atmosphere) with a stir bar (cooled in an ice water bath). After pouring the first 40 mL of the resulting mixture, the remainder is collected. The resulting mixture is stirred at room temperature for 8 hours.Neutral alumina (approximately 300 g) is washed with ethyl acetate, added to the mixture, followed by an equal volume of petroleum ether. The entire mixture is then filtered through a sintered glass; the solids are washed with another volume of petroleum ether. The filtrate is washed with 10% H3PO4 aq. (3x150 mL), NaHCO3 sat. soln. (100 mL), NaCl sat. soln. (150 mL). The organic phase is concentrated, diluted with petroleum ether on a pad of neutral alumina (600 g; prewashed with ethyl acetate, then with petroleum ether). The product is eluted with petroleum ether, concentrated, and dried in vacuo. Yellow liquid. 5.2 g (40% yield). The product obtained from aqueous washes can also be purified by vacuum distillation (42-46 °C, 0.1 mbar). Compound IIb can also be prepared from TMSCF3 (molar ratio TMSCF3 : Cy2NLi = 2.5 : 1; T = 36 °C, 1 mL / min each solution) using the same apparatus. 1H NMR (300 MHz, CDCl3) δ 2.76 – 2.63 (m, 2H), 1.66 (m, 8H), 1.51 – 1.43 (m, 2H), 1.18 – 0.90 (m, 10H). 19F NMR: -106.9 (dd, J = 67, 37 Hz, 1 F), -117.4 (dd, J = 118, 37 Hz, 1 F), 118.1 (dd, J = 118, 67 Hz, 1 F). Part 2: Preparation of dicyclohexyl(trifluorovinyl)amine of formula (IIb), of N-(trifluorovinyl)-2,2,6,6-tetramethylpiperidine of formula (IIa), comparison between different conditions Tables 1 and 2 below group together 4 syntheses carried out according to method A or method B as well as the products obtained and the yields (Table 1). Table 2 groups together the best conditions tested. Table 1 Table 2The terms “yield 1” refer to the 19F NMR yield based on R2NLi.The terms “yield 2” refer to the 19F NMR yield based on CF3Y.Method A: 3 R2NLi + 2 CHF3 -> R2N-CF=CF2 + 2 R2NH + 1 LiFMethod B: 1 R2NLi + 2 TMSCF3 > R2N-CF=CF2 + 2 TMSF + 1 LiF. Batch conditions: Solution A (1 mL) is added rapidly via a syringe to a sealed tube containing solution B stirred at the indicated temperature. The mixture is warmed to room temperature, and then the internal standard is added. The mixture is transferred to an NMR tube with a septum previously inerted with N2. N-(Trifluorovinyl)-2,2,6,6-tetramethylpiperidine (formula IIa) was prepared according to the continuous flow method described for dicyclohexyl(trifluorovinyl)amine(IIb). 1H NMR (300 MHz, CDCl3) δ 1.61 – 1.38 (m, 6H), 1.29 (s, 6H), 1.14 (s, 6H).19F NMR (282 MHz, CDCl3) δ -109.58 (dd, J = 70.0, 34.4 Hz), -116.79 (dd, J =116.2, 70.0 Hz), -123.12 (dd, J = 116.3, 34.5 Hz) Part 3: Syntheses of other trifluorovinylamines Other compounds of formula (II) were also synthesized according to the following protocols: Compound IIb from sodium amide: A 100 mL two-necked flask equipped with a filter suitable for filtration under argon, a stir bar, and a septum was charged with 8.5 g of 30 wt% Na dispersion in toluene and then purged with argon. An argon balloon was attached via a septum. To this flask were successively added cyclohexane (30 mL), Cy2NH (32 mL), and isoprene (17 mL). This mixture was stirred under ultrasound for 3 hours, then stirred for 18 hours at room temperature. At this point, a large white precipitate can be observed. To promote complete conversion of the sodium, several cycles of sonication and agitation can be applied. The mixture is then filtered under argon.The recovered solid was washed with 50 mL of cyclohexane and dried under vacuum (0.1 mbar) without being exposed to the ambient atmosphere. The dried white solid (12 g) was stored in a glove box. The purity of Cy2NNa can be assessed by titration with N-benzylbenzamide in THF at 0 °C. For use in the synthesis of IIb, Cy2NNa is dissolved in THF (at a concentration of 0.25 M) under argon at 0 °C and then stored at -20 °C throughout the operation. The continuous flow synthesis of IIb using Cy2NNa is carried out in the same manner as previously described for Cy2NLi (the reactor and pre-cooling tubes are immersed in an ice bath), using a Syrris ASIA pump and supplying the Cy2NNa solution directly from the cooled reservoir.Using this procedure with a flow rate of 2 mL / min for the CHF3 solution and 4 mL / min for the Cy2NNa solution, a 32% yield of IIb was obtained (measured by fluorine-19 NMR with 4-fluorotoluene as internal standard, D1 = 10 s). Compound IId: n-Butyllithium (1.1 mmol, dissolved in 2.4 M hexanes) was added dropwise to a stirred solution of isopropylamine (1.1 mmol) in 3 mL of THF (cooled in an ice bath). After 10 minutes, TMSCF3 (2.1 mmol) was added all at once. A dark gray color appears immediately, which quickly changes to dark brown. The mixture gels. After 20 minutes at room temperature, 0.5 mL was mixed with EtOAc-brine. 20 µL of 4-fluorotoluene (0.18 mmol) was added as an internal standard, and the yield was measured by fluorine-19 NMR. Compound IIe: n-Butyllithium (1.1 mmol, dissolved in 2.4 M hexanes) was added dropwise to a stirred solution of N-methylaniline (1.1 mmol) in 3 mL of THF (cooled in an ice bath). A cloudy solution forms. After 15 minutes, TMSCF3 (2.1 mmol) was added all at once. The initially cloudy solution becomes clear and a slight precipitate appears. After 30 minutes at room temperature, 0.5 mL was mixed with EtOAc-brine. 20 µL of 4-fluorotoluene (0.18 mmol) was added as an internal standard, and the yield was measured by fluorine 19 NMR. Compound IIf: n-Butyllithium (1.1 mmol, dissolved in 2.4 M hexanes) was added dropwise to a stirred solution of N-allylaniline (1.1 mmol) in 3 mL of THF (cooled in an ice bath). After 15 minutes, TMSCF3 (2.1 mmol) was added all at once. A dark gray color appears briefly, then returns to a light yellow tint. After 20 minutes at room temperature, 0.5 mL was mixed with EtOAc-brine.20 µL of 4-fluorotoluene (0.18 mmol) was added as an internal standard, and the yield was measured by fluorine 19 NMR. Compound IIg: n-Butyllithium (1.1 mmol, dissolved in 2.4 M hexanes) was added dropwise to a stirred solution of carbazole (1.1 mmol) in 3 mL of THF (cooled in an ice bath). A cloudy solution formed. After 15 minutes, TMSCF3 (2.1 mmol) was added all at once. After 16 h at room temperature, 0.5 mL was mixed with EtOAc-brine. 20 µL of 4-fluorotoluene (0.18 mmol) was added as an internal standard, and the yield was measured by fluorine-19 NMR. Compound IIh: n-Butyllithium (1.1 mmol, dissolved in 2.4 M hexanes) was added dropwise to a stirred solution of pyrrolidone (1.1 mmol) in 3 mL of THF (cooled in an ice bath). After 15 min, TMSCF3 (2.1 mmol) was added all at once. After 16 h at room temperature, 0.5 mL was mixed with EtOAc-brine.20 µL of 4-fluorotoluene (0.18 mmol) was added as an internal standard, and the yield was measured by fluorine 19 NMR. These compounds are grouped in Table 3 belowTable 3 Amine Formula Yield evaluated by NMR. 19 F Chemical shift (^ based on ppm) quantity observed in NMR 19F d’amidure de lithium ou de sodium Cy2NH -108.4 (dd, J = 67, 37 Hz, 1 44% F), -117.0 (dd, J = 118, 37 Hz, 1 F), 118.9 (dd, J = 118, 67 Hz, 1 F). Cy2NNa -108.3 (dd, J = 67, 37 Hz, 1 30% F), -117.0 (dd, J = 118, 37 Hz, 1 F), 118.9 (dd, J = 118, 67 Hz, 1 F). iPr2NH -108.5 (dd, J = 72, 35 Hz, 1 18% F), -119.4 (dd, J = 72, 117 Hz, 1 F), -121.1 (ddt, J = 35, 117, 5 Hz, 1 F). PhNH(Me) -108.3 (dd, J = 74, 38 Hz, 1 12% F), 120.6 (dd, J = 114, 74 Hz, 1 F), -140.6 (ddq, J = 114, 38, 3 Hz, 1 F). PhNH(allyl) 1% -107.8 (dd, J = 72, 39 Hz, 1F), -119.3 (dd, J = 113, 72 Hz, 1 F), -138.2 (dd, J = 113, 39, 1 F). Carbazole -102.4 (dd, J = 66, 43 Hz, 1 10% F), -116.2 (dd, J = 114, 66 Hz, 1 F), -143.5 (dd, J = 114, 43 Hz, 1 F). 2- -107.5 (dd, J = 74, 43 Hz, 1 pyrrolinone 3%F), -119.6 (dd, J = 111, 74 Hz, 1 F), -149.5 (dd, 111, 43 Hz, 1 F).Part 4: General protocol of the reaction between dicyclohexyl(trifluorovinyl)amine and a nucleophile Dicyclohexyl(trifluorovinyl)amine (100 mg, 0.38 mmol) is dissolved in dry DCM (2.5 mL) under Ar. The nucleophile (arene, sulfoxide, depending on the desired final compound) (0.32 mmol) is added. The mixture is cooled to -78°C. BF3-Et2O (54 mg, 47 mL, 0.38 mmol) is added dropwise. The mixture is allowed to warm to room temperature and stirred for 1 h. The mixture is diluted with ethyl acetate (10 mL), washed with NaHCO3 sat. soln. (5 mL), NaCl sat. soln. (5 mL), dried over MgSO4, evaporated. The product is purified by column chromatography. Part 5: Reaction scheme and results obtained for the reaction between dicyclohexyl(trifluorovinyl)amine and a nucleophile chosen from aromatics substituted by an electron donating group (Electron Donating Group, en.

[0003] English; known by the abbreviated expression "EDG") Part 6: Reaction scheme and results obtained for the reaction between dicyclohexyl(trifluorovinyl)amine and a nucleophile chosen from alkynes. The yields obtained exceed 50% for compounds (VIIIa) to (VIIId). Characterization of the compounds obtained: (VIa) 1H NMR (300 MHz, CDCl3) δ 3.89 (s, 3 H), 6.27 (t, J = 54 Hz, 1 H), 6.98 (m, 2H), 8.06 (m, 2 H); 19F NMR (282 MHz, CDCl3) δ -121.4 (d, J = 54 Hz).(VIc) 1H NMR (300 MHz, CDCl3) δ 3.28 (t, J = 8.8 Hz, 2 H), 4.70 (t, J = 8.8 Hz, 2 H),6.25 (t, J = 54 Hz, 1 H), 6.86 (d, J = 9.4 Hz, 1 H), 7.93 (d, J = 9.4 Hz, 1 H), 7.94 (s, 1 H); 19F NMR (282 MHz, CDCl3) δ -121.1 (d, J = 54 Hz).(VId) 1H NMR (300 MHz, CDCl3) δ 6.08 (s, 2 H), 6.23 (t, J = 54 Hz, 1 H), 6.90 (d, J= 8.0 Hz, 1 H), 7.49 (s, 1 H), 7.70 (d, J = 8.0 Hz, 1 H); 19F NMR (282 MHz, CDCl3) δ-121.1 (d, J = 54 Hz).(VIe) 1H NMR (300 MHz, CDCl3) δ 8.00 (d, J = 9.0 Hz, 2H), 6.88 (d, J = 199.0 Hz,2H), 6.24 (t, J = 53.9 Hz, 1H), 3.91 – 3.80 (m, 4H), 3.43 – 3.30 (m, 4H).; F NMR(282 MHz, CDCl3) δ -121.1 (d, J = 54 Hz).(VIh) 1H NMR (300 MHz, CDCl3) δ 6.86 (t, J = 53.5 Hz, 1 H), 7.32 (dd, J = 8.5 and1.9 Hz, 1 H), 7.63 (d, J = 1.9 Hz, 1 H), 8.16 (d, J = 8.5 Hz, 1 H), 8.53 (s, 1 H), 12.52(br.s, 1H); 19F NMR (282 MHz, CDCl3) δ -124.2 (d, J = 53.5 Hz).(VIIIa) 1H NMR (300 MHz, DMSO-d6) δ 7.82 (d, J = 16.1 Hz, 1H), 7.53 – 7.47 (m,2H), 7.43 – 7.34 (m, 2H), 6.95 (dt, J = 16.1, 1.2 Hz, 1H), 5.86 (t, J = 54.1 Hz, 1H),1.27 (s, 9H); 19F NMR (282 MHz, DMSO-d6) δ -121.01 (d, J = 54.2 Hz).(VIIIb) 1H NMR (300 MHz, DMSO-d6) δ 5.93 (t, J = 54 Hz, 1 H), 7.03 (dt, J = 16.1and 1.0 Hz, 1 H), 7.17 (m, 1 H), 7.32 (m, 1 H), 7.41 (m, 2 H), 7.84 (d, J = 16.1 Hz);19F NMR (282 MHz, DMSO-d6) δ -112.4 (m, 1 F), -126.6 (d, J = 54 Hz, 2 F).

Claims

Claims1. Process for the preparation of a trifluorovinylamine of formula (II) using a molecule of formula (I), with n= 1 or 2: in which the groups R1 and R2 together form a heterocycle or independently represent a functional group chosen from a hydrogen and an aliphatic chain chosen from at least one of the following chains: a linear, branched, cyclic, substituted and unsubstituted chain; the aliphatic chain being chosen from a group C 1-12 alkyl, C 1-12 heteroalkyl, C 6-10 aryl and C 4- 10heteroaryl, ; each of the alkyl, heteroalkyl, aryl and heteroaryl groups defined above optionally comprising one or more substituents comprising at least one atom or function chosen from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-; -C(=O)O-; -C(=O)S- and -C(=O)N-; R1 and R2 preferably represent a branched or cyclic alkyl chain; and in which X is a halogen preferably chosen from -F and -Cl, said process implementing the reaction of the compound of formula (I) with the compound of formula (V) below: following formula (III); to form the compound of following formula (IV): which reacts with the compound of formula (V) to form the compound of formula (II), all reactions are preferably carried out in a solvent comprising THF, and the metal M is preferably selected from Li and Na.

2. Method according to claim 1, characterized in that X is a fluorine atom and in that said method therefore implements the following two reactions: ; steps 1- and 2- preferably being carried out in a solvent comprising THF, and the metal M is preferably selected from Li and Na.

3. Process for the preparation of the compound of formula (II) according to claim 1, characterized in that X is a fluorine atom and in that it implements the following reaction, wherein the metal M is preferably an alkali metal advantageously selected from Li and Na; and the reaction solvent comprises THF.

4. A process for preparing the compound of formula (II) according to any one of claims 1 to 3, wherein the compound (II) is selected from the following compounds (IIa-IIb):

5. A process for the synthesis of a compound according to formula (VI), implementing the process for preparing the compound of formula (II) according to any one of claims 1 to 4, and comprising the following subsequent steps: R3 being a functional group selected from hydrogen and an aliphatic chain selected from at least one of the following chains: a linear, branched, cyclic, substituted and unsubstituted chain; the aliphatic chain being selected from a C1-12alkyl, C1-12heteroalkyl, C6-10aryl and C4-10heteroaryl group; each of said alkyl, heteroalkyl, aryl and heteroaryl groups optionally comprising one or more substituents comprising at least one atom or function selected from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-;; -C(=O)O-; -C(=O)S- and -C(=O)N-; Q representing a functional group selected from hydrogen and a substituent comprising an element having an electronegativity lower than that of carbon, in particular a metal M', M' preferably being chosen from Mg and Li; and m being an integer less than 5, preferably from 1 to 3.6.A process for synthesizing a compound according to claim 5, wherein the compound of formula (VI) is a compound of formula (VI.1):. in which the substituent Ar 1 is selected from C6-10aryl and C4-10heteroaryl groups; each of the aryl and heteroaryl groups optionally comprising one or more substituents comprising at least one atom or function chosen from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-; -C(=O)O-; -C(=O)S- and -C(=O)N-; andpreferably, (VI.1) is selected from the following compounds (VIa-VIh):

7. A process for the synthesis of a compound according to formula (VIII), implementing the process for preparing the compound of formula (II) according to any one of claims 1 to 4, and comprising the following subsequent steps: R5 and R6 independently representing a functional group chosen from a hydrogen and an aliphatic chain chosen from at least one of the following chains: a linear, branched, cyclic, substituted and unsubstituted chain; the aliphatic chain being chosen from a C group 1-12 alkyl, C 1-12 heteroalkyl, C6-10aryl and C4-10heteroaryl; each of the alkyl, heteroalkyl, aryl and heteroaryl groups optionally comprising one or more substituents comprising at least one atom or function chosen from -F; -Cl; -Br; -I; -NO2; -CN; -CF3;-OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-; ; -C(=O)O-; -C(=O)S- and -C(=O)N-; andq being an integer less than 5, preferably from 1 to 3.

8. A process for the synthesis of a compound according to claim 7, wherein the compound of formula (VIII) is selected from the following compounds (VIIIa-VIIId):

9. Process for the synthesis of a compound according to formula (IX), implementing the process for the preparation of the compound of formula (II) according to any one of claims 1 to 4, according to the following reaction:

10. Process for the synthesis of a compound according to formula (X), implementing the process for the preparation of the compound of formula (II) according to any one of claims 1 to 4, according to the following reaction:

11. A compound obtained from fluoroform of formula (I) according to a process according to any one of claims 1 to 4, said compound being represented by the following general formula (IIc): wherein the groups R7, R8, R11, and R12 independently represent a functional group selected from hydrogen and an aliphatic chain selected from at least one of the following chains: a linear, branched, cyclic, substituted and unsubstituted chain; the aliphatic chain being selected from a C1-11alkyl, C1-11heteroalkyl, C6-9aryl and C4-9heteroaryl group; each of the alkyl, heteroalkyl, aryl and heteroaryl groups optionally comprising one or more substituents comprising at least one atom or function selected from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-; -S(=O)-; -SO2-; -SO3-; -C(=O)O-; -C(=O)S- and -C(=O)N-; the groups R9 and R10:- taken independently, represent a functional group as defined for the groups R7, R8, R11, and R12;and- taken together, represent a single cyclic aliphatic chain comprising the C atoms carrying the groups R9 and R10 and the N atom carrying said C atoms carrying R9 and R; 10 ; the cyclic aliphatic chain being chosen from a group C 1-12 alkyl, C 1-12 heteroalkyl, each of said alkyl groups optionally comprising one or more substituents comprising at least one atom or function chosen from -F; -Cl; -Br; -I; -NO2; -CN; -CF3; -OH; -O-; -S-; -C(=O)-;-S(=O)-;; -SO3-; -SO2; -C(=O)O-; -C(=O)S- and -C(=O)N-; excluding compounds (IId-IIf), in which the groups R7, R8, R11, and R12 are chosen from four hydrogens and the groups R9 and R 10 are included in the nitrogen cycles identified in (IId-IIf):

12. Compound according to claim 11, wherein the compound of formula (IIc) is selected from the following compounds (IIa-IIb):

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