Shelf-stable reagents and uses thereof for radical pentafluorosulfanylation

Abstract

The present invention relates to imine or amine reagents of formula (I), (II), or (III) substituted by a pentafluorosulfanyl (SF5) group, and processes of preparation thereof. The invention further relates to the use of the imine or amine reagents of formula (I), (II), or (III) for preparing SF5-susbstituted molecules.

Description

[0001] SHELF-STABLE REAGENTS AND USES THEREOF FOR RADICAL

[0002] PENTAFLUORO SULF ANYLATION

[0003] TECHNICAL FIELD

[0004] The present invention relates to the field of organic chemistry, at particular pentafluorosulfanylsubstituted imine or amine reagents, processes of preparation thereof. The invention further relates to their use for preparing SFs-susbstituted molecules suitable for various fields, such as pharmaceuticals, agrochemicals, and materials.

[0005] TECHNICAL BACKGROUND

[0006] In recent decades, fluorinated motifs have been studied and used in various fields, such as like pharmaceuticals, agrochemicals, and materials science. Among fluorinated groups, the trifluoromethyl group (CFs) including its derivatives, such as OCFs and SCF3, have risen to prominence, and were prized for their remarkable blend of high electronegativity and lipophilicity. The impact of the CF3 group has been recognized as essential in the development of groundbreaking drugs, such as for instance, Sitagliptin for diabetes, Paxlovid for CO VID-19 treatment, and Lenacapavir for HIV-1.

[0007] However, the CF3 motif carries a major drawback: it is part of the per- and polyfluorinated compound (PFAS) family, notorious for their environmental persistence and harmful effects. When bioactive compounds containing CF3 degrade, they can produce trifluoroacetic acid (TFA), a "forever chemical" that resists natural breakdown and accumulates in ecosystems. In light of these concerns, the European Union is taking bold action, moving to ban the production, use, and supply of PFAS. This regulatory shift will have profound implications, limiting access to these once-essential molecules.

[0008] Given these challenges, there is a need to develop new, straightforward approaches, and alternative motifs. In this context, the pentafluorosulfanyl (SFs) group emerges as a promising alternative for the next generation of fluorinated molecules thanks to its higher electronegativity and lipophilicity compared to the CF3 group. In addition, studies on the environmental degradation of SFs-substituted molecules have shown that the degradation process yields environmentally benign products. However, although the SFs motif has been known for more than 70 years, a significant bottleneck in its development has been the lack of effective reagents and direct methods for synthesizing SFs-containing molecules. Currently, Cl-SFs is the most commonly used reagent, but it is a highly toxic gas with very limited reactivity, primarily facilitating chloropentafluorosulfanylation reactions of unsaturated compounds under strict temperature conditions. Despite efforts to address the toxicity and availability issues and to expand the applications of Cl-SFs, progress has been limited.

[0009] Thus, the development of shelf-stable SFs reagents remains one of the most pressing challenges in modern organofluorine chemistry. Today, there is therefore still a need to provide new stable SFs-substituted reagents that are easy to prepare, use, and manipulate and non-toxic, in the synthesis of various molecules in a wide range of applications. The present invention seeks to meet these and other needs.

[0010] SUMMARY OF THE INVENTION

[0011] In this context, the inventors have developed, proposed, and prepared new SFs-substituted imine or amine reagents. The inventors have further demonstrated that these new reagents are well suitable for the synthesis of SFs-containing molecules, particularly late-stage SFs- functionalization of these complex molecules.

[0012] The present invention thus provides a process for preparing a compound of formula (I): wherein: Ri and R2 represent independently a radical selected in a group consisting of:

[0013] • a hydrogen,

[0014] • a radical selected in a group consisting of a (Ci-Ce)alkyl, and a 5-14 membered ring, said radical is optionally substituted by at least one radical selected in a group consisting of: a halogen, a (Ci-Ce)alkyl, a (Ci-Ce)alkyloxy, a nitro, a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), and

[0015] • a CO-O-Ra or a CO-Rb with Ra and Rb represent independently a radical selected in a group consisting of: a (Ci-Ci2)alkyl optionally substituted by a (C2-Ci2)alkynyl or by a 5- 14 membered ring optionally substituted by a (Ci-Ce)alkyl, and and a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl; or Ri and R2 may form together a 5-14 membered ring optionally substituted by a radical selected in a group consisting of:

[0016] • a halogen,

[0017] • a (Ci-Ce)alkyl,

[0018] • a (Ci-Ce)alkyloxy,

[0019] • a nitro,

[0020] • a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and

[0021] • a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), with the proviso that when one of Ri and R2 is a hydrogen, then the other is not a hydrogen; and the stereoisomers, and the salts thereof; comprising the following steps of: a) reacting pentafluorosulfanyldichloramine (SF5NCI2) with a compound of formula (I’): with Y represents N2 or O, and

[0022] Ri and R2 are such as above defined; and b) recovering said compound of formula (I).

[0023] The present invention further provides a compound of formula (I) obtained by the process as defined herein. The present invention also provides a compound of formula (I): Ri and R2 represent independently a radical selected in a group consisting of:

[0024] • a hydrogen,

[0025] • a radical selected in a group consisting of a (Ci-Ce)alkyl, and a 5-14 membered ring, said radical is optionally substituted by at least one radical selected in a group consisting of: a halogen,

[0026] - a (Ci-Ce)alkyl, a (Ci-Ce)alkyloxy, a nitro,

[0027] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), and

[0028] • a CO-O-Ra or a CO-Rb with Ra and Rb represent independently a radical selected in a group consisting of: a (Ci-Ci2)alkyl optionally substituted by a (C2-Ci2)alkynyl or by a 5- 14 membered ring optionally substituted by a (Ci-Ce)alkyl, and and a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl; or Ri and R2 may form together a 5-14 membered ring optionally substituted by a radical selected in a group consisting of:

[0029] • a halogen,

[0030] • a (Ci-Ce)alkyl,

[0031] • a (Ci-Ce)alkyloxy,

[0032] • a nitro,

[0033] • a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and

[0034] • a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), with the proviso that when one of Ri and R2 is a hydrogen, then the other is not a hydrogen; and the stereoisomers, and the salts thereof.

[0035] In a particular embodiment, Ri represents a phenyl optionally substituted by a radical selected in a group consisting of a bromine, a chorine, a fluorine, a methyl, a methoxy, a nitro, a CO-O- methyl.

[0036] In a particular embodiment, R2 represents a 5-14 membered ring, preferably selected in a group consisting of an aryl or a heteroaryl, said 5-14 membered ring being optionally substituted by at least one radical selected in a group consisting of:

[0037] - a halogen, preferably a fluorine, a bromine, or a chlorine,

[0038] - a (Ci-Ce)alkyl, preferably a methyl,

[0039] - a (Ci-Ce)alkyloxy, preferably a methoxy,

[0040] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, preferably a O-C(CH3)2-CO-O-CH(CH3)2, and

[0041] - a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), preferably a CH(CH3)-CO-O- (adamantanyl).

[0042] In a further particular embodiment, R2 represents a CO-O-Ra or a CO-Rb, preferably a CO-O- Ra, with Ra and Rb represent independently a radical selected in a group consisting of:

[0043] - a (Ci-Ci2)alkyl optionally substituted by a radical selected by a (C2-Ci2)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and

[0044] - a 5-14 membered ring optionally substituted by a radical selected in a group consisting of a (Ci-C24)alkyl.

[0045] Particularly, Rarepresents a radical selected in a group consisting of a methyl, an ethyl, an hexyl, an isobutyl, a 2-methylbutyl, a 2-methylbut-3-yn-2yl, a tetrahydrofuranyl, a cyclohexyl, a 2-isopropyl-5-methylcyclohexyl, a 2-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl, an adamantanyl, a 2,2,7,7-tetramethyltetrahydro-5H-bis([l,3]dioxole)[4,5-b:4’,5’-d]pyran-5- yl)methyl, a phenyl, and a tetramethyl-2-(4,8,12-trimethyltridecyl)-chroman-6-yl.

[0046] In a preferred embodiment, a compound of formula (I) according to the invention is selected in a group consisting of:

[0047] - N-(pentafluoro-k6-sulfaneyl)-l,l-diphenylmethanimine (2a);

[0048] - l,l-Bis(4-fluorophenyl)-N-(pentafluoro-k6-sulfaneyl)methanimine (2b);

[0049] - l,l-Bis(4-bromophenyl)-N-(pentafluoro-k6-sulfaneyl)methanimine (2c);

[0050] - l , l -Bis(4-chlorophenyl)-N-(pentafluoro-A6-sulfaneyl)methanimine (2d); - N-(pentafluoro-X6-sulfaneyl)-l,l-di-p-tolylmethanimine (2e);

[0051] - 1,1 -Bis(4-methoxyphenyl)-N-(pentafluoro-Z6-sulfaneyl)methanimine (2f);

[0052] - N-(pentafluoro-X6-sulfaneyl)-9H-fluoren-9-imine (2g);

[0053] - (Z)-l -(naphthal en-2-yl )-N-(pentafluoro-X6-sulf aneyl)- l -phenyl methani mine (2h);

[0054] - (E)- 1 -(4-nitrophenyl)-N-(pentafluoro-X6-sulfaneyl)- 1 -phenylmethanimine (2i);

[0055] - (E)-l -(3, 4-dimethylphenyl)-N-(pentafluoro-X6-sulfaneyl)-l -phenylmethanimine (2j);

[0056] - (E)-l-(2-methoxyphenyl)-N-(pentafluoro-Z6-sulfaneyl)-l -phenylmethanimine (2k);

[0057] - (Z)-N-(pentafluoro-Z6-sulfaneyl)-l -phenyl- l-(pyri din-3 -yl)methanimine (21);

[0058] - (E)- 1 -(4-bromophenyl)-N-(pentafluoro-Z6-sulfaneyl)- 1 -phenylmethanimine (2m);

[0059] - Isopropyl (E)-2-(4-((4-chlorophenyl)((pentafluoro-X6-sulfaneyl)imino)methyl)phenoxy)-2- methylpropanoate (2n);

[0060] (lR,3S,5r,7r)-Adamantan-2-yl 2-(3-((Z)-((pentafluoro-Z6- sulfaneyl)imino)(phenyl)methyl)phenyl)propanoate (2o);

[0061] - Ethyl (Z)-2-((pentafluoro-Z6-sulfaneyl)imino)-2-phenylacetate (2p);

[0062] - Ethyl (Z)-2-(4-bromophenyl)-2-((pentafluoro-Z6-sulfaneyl)imino)acetate (2q);

[0063] - Ethyl (Z)-2-(4-nitrophenyl)-2-((pentafluoro-Z6-sulfaneyl)imino)acetate (2r);

[0064] - Methyl (Z)-4-(2-methoxy-2-oxo-l-((pentafluoro-X6-sulfaneyl)imino)ethyl)benzoate (2s);

[0065] - Ethyl (Z)-2-(4-methoxyphenyl)-2-((pentafluoro-Z6-sulfaneyl)imino)acetate (2t);

[0066] - Ethyl (Z)-2-((pentafluoro-Z6-sulfaneyl)imino)-2-(o-tolyl)acetate (2u);

[0067] - Hexyl (Z)-2-((pentafluoro-Z6-sulfaneyl)imino)-2-phenylacetate (2v);

[0068] - Isobutyl (Z)-2-((pentafluoro-Z6-sulfaneyl)imino)-2-phenylacetate (2w);

[0069] - (S)-2-Methylbutyl (Z)-2-((pentafluoro-Z6-sulfaneyl)imino)-2-phenylacetate (2x);

[0070] - 2-Methylbut-3-yn-2-yl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2y);

[0071] - Tetrahydrofuran-3-yl (Z)-2-((pentafluoro-Z6-sulfaneyl)imino)-2-phenylacetate (2z);

[0072] - Cyclohexyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2aa);

[0073] (2R,5S)-2-Isopropyl-5-methylcyclohexyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2- phenylacetate (2ab);

[0074] 2-((lR,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl (Z)-2-((pentafluoro-Z6- sulfaneyl)imino)-2-phenylacetate (2ac);

[0075] - (lr,3r,5r,7r)-Adamantan-2-yl (Z)-2-((pentafluoro-Z6-sulfaneyl)imino)-2-phenylacetate (2ad);

[0076] ((3aS,5S,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl (Z)-2-((pentafluoro-Z6-sulfaneyl)imino)-2-phenylacetate (2ae);

[0077] - Phenyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2af); (S)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl (Z)-2- ((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2ag); and

[0078] - (Z)-2-((pentafluoro-X6-sulfaneyl)imino)- 1 ,2-Diphenylethan- 1 -one (2ah).

[0079] A further object of the invention is a process for preparing pentafluorosulfanyldi chloramine comprising the following steps of: aOl) reacting 2,3,4,5,6-pentafluorobenzamide with octasulfur (Ss), trichloroisocyanuric acid, and tetrabutylammonium chloride in acetonitrile; a02) adding AgF2 powder to the mixture of step aOl); a03) adding a mixture comprising trichloroisocyanuric acid and potassium fluoride in acetonitrile in the mixture of step a02); and a04) recovering pentafluorosulfanyldichloramine (SF5NCI2).

[0080] Another object of the invention is a use of a compound of formula (I) as defined herein, for preparing a molecule comprising a pentafluorosulfanyl (SFs) group or for incorporating a pentafluorosulfanyl (SFs) group in a molecule.

[0081] An object of the invention is also a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: al) reacting a compound of formula (I) as defined herein with a molecule comprising a styrene unit in presence of thioxanthone (TXO) under blue LED irradiation; and bl) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0082] A particular molecule is selected in a group consisting of:

[0083] - N-(2-(pentafluoro-X6-sulfaneyl)-l-(p-tolyl)ethyl)-l, 1-diphenylmethanimine (4a);

[0084] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 -(m-tolyl)ethyl)- 1 , 1 -diphenylmethanimine (4b);

[0085] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 -(o-tolyl)ethyl)- 1 , 1 -diphenylmethanimine (4c);

[0086] - N-(l-(4-(tert-butyl)phenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)-l, 1-diphenylmethanimine (4d);

[0087] - 4-( l -((di phenyl methyl ene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Phenyl acetate (4e);

[0088] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 -phenylethyl)- 1 , 1 -diphenylmethanimine (4f);

[0089] - N-( 1 -(naphthal en-2-yl )-2-(pentafl uoro-X6-sulfaneyl jethyl )- 1 , 1 -diphenylmethanimine (4g);

[0090] - N-( 1 -(4-chlorophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4h);

[0091] - N-(l-(4-bromophenyl)-2-(pentafluoro-Z6-sulfaneyl)ethyl)-l, 1 -diphenylmethanimine (4i);

[0092] - N-(l-(4-iodophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1,1 -diphenylmethanimine (4j);

[0093] - N-( 1 -([ 1 , 1l-biphenyl]-4-yl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4k); - 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Benzonitrile (41);

[0094] - N-( 1 -(4-nitrophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4m);

[0095] - 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Benzaldehyde (4n);

[0096] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 , 1 -diphenylethyl)- 1 , 1 -diphenylmethanimine (4o);

[0097] - N-( 1 -(pentafluoro-X6-sulfaneyl)-2-phenylpropan-2-yl)- 1 , 1 -diphenylmethanimine (4p);

[0098] - N-(2-(pentafluoro-X6-sulfaneyl)-l-(thiophen-2-yl)ethyl)-l, 1 -diphenylmethanimine (4q);

[0099] (1 S,2R,5S)-2-isopropyl-5-methylcyclohexyl 4-(l-((diphenylmethylene)amino)-2- (pentafluoro-X6-sulfaneyl)ethyl)benzoate (4r);

[0100] ((S)-4-(prop- 1 -en-2-yl)cyclohex- 1 -en- 1 -yl)Methyl 4-( 1 -((diphenylmethylene)amino)-2-

[0101] (pentafluoro-X6-sulfaneyl)ethyl)benzoate (4s);

[0102] ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (4t);

[0103] 2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(l-

[0104] ((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (4u);

[0105] (S)-3,7-dimethyloct-6-en-l-yl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6- sulfaneyl)ethyl)Benzoate (4v);

[0106] 4-Formyl-2-methoxyphenyl 4-( l -((di phenyl methylene)amino)-2-(pentafluoro-A6- sulfaneyl)ethyl)benzoate (4w);

[0107] (8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,ll,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (4x); and

[0108] (R)-2, 5 ,7, 8-Tetramethy l-2-((4R, 8R)-4, 8, 12-trimethyltridecyl)chroman-6-yl 4-( 1 -

[0109] ((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (4y).

[0110] An object of the invention is also a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a2) reacting a compound of formula (I) as defined herein with a molecule comprising a styrene unit in presence of diethyl 2,6-dimethyl-l,4-dihydropyridine-3,5-dicarboxylate, [Ir(dF(CF3)ppy)2dtbbpy]PFe, and chlorohydric acid, under blue LED irradiation; and b2) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0111] A particular molecule is selected in a group consisting of:

[0112] - (4-(tert-butyl)phenethyl)Pentafluoro-X6-sulfane (5b); - (4-(chloromethyl)phenethyl)Pentafluoro-X6-sulfane (5e);

[0113] - Pentafluoro(4-iodophenethyl)- X6-sulfane (5h);

[0114] - (2-([l,l'-biphenyl]-4-yl)ethyl)Pentafluoro-X6-sulfane (5j);

[0115] - (1 S,2R,5S)-2-Isopropyl-5-methylcyclohexyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5k);

[0116] (S)-(4-(prop- 1 -en-2-yl)cyclohex- 1 -en- 1 -yl)Methyl 4-(2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (51);

[0117] ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5m);

[0118] 2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (5n);

[0119] - (S)-3,7-Dimethyloct-6-en-l-yl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5o);

[0120] - 4-Formyl-2-methoxyphenyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5p); and

[0121] (8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,ll,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5q).

[0122] A further object of the invention is a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a3) reacting a compound of formula (I) as defined in any one of claims 2 to 8 with a molecule comprising an azabicyclobutanyl in presence of thioxanthone (TXO) and ethyl acetate under blue LED irradiation; and b3) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0123] A particular molecule is selected in a group consisting of:

[0124] - N-( l-(pentafluoro-X6-sulfaneyl)-3-phenylazeti din-3 -yl)- 1, 1-diphenylmethanimine (3a);

[0125] - l,l-bis(4-fluorophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3b);

[0126] - l,l-bis(4-bromophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3 c)

[0127] - l,l-bis(4-chlorophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3d);

[0128] - N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazeti din-3 -yl)-l,l-di-p-tolylmethanimine (3e); l,l-bis(4-methoxyphenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3- yl)methanimine (3f); - 7V-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)-9JH-fluoren-9-imine (3g);

[0129] 1 -(naphthal en-2-yl)-N-(l -(pentafl uoro-X6-sulf aneyl )-3 -phenylazeti din-3 -yl)- 1 - phenylmethanimine (3h); l-(4-nitrophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3 -phenylazeti din-3 -yl)-l- phenylmethanimine (3i); l-(3,4-dimethylphenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3j);

[0130] 1 -(2-methoxyphenyl)-N-(l -(pentafl uoro-X6-sulf aneyl )-3 -phenylazeti din-3 -yl)- 1 - phenylmethanimine (3 k);

[0131] N-(l -(pentafl uoro-k6-sulfaneyl )-3 -phenylazeti din-3 -yl)- 1 -phenyl- 1 -(pyri din-3 - yl)methanimine (31); l-(4-bromophenyl)-N-(l-(pentafluoro-X.6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3m);

[0132] 2-(4-((4-chlorophenyl)((l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3- yl)imino)methyl)phenoxy)-2-methylpropanoate (3n);

[0133] - N-( 1 -(pentafluoro-X.6-sulfaneyl)-3 -(p-tolyl)azetidin-3 -yl)- 1 , 1 -diphenylmethanimine (3 a 1 );

[0134] N-( 1 -(pentafluoro-X6-sulfaneyl)-3 -(4-(trifluoromethyl)phenyl)azeti din-3 -yl)- 1,1- diphenylmethanimine (3a2);

[0135] (3-((diphenylmethylene)amino)-l-(pentafluoro-X6-sulfaneyl)azetidin-3- yl)(phenyl)methanone (3a3); and

[0136] N-2-methyl- l-(pentafluoro-X.6-sulfaneyl)-3 -phenylazeti din-3 -yl)- 1,1 -diphenylmethanimine (3a4).

[0137] A further object of the invention is a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a4) reacting a compound of formula (I) as defined in any one of claims 2 to 8 with a molecule comprising a bicyclobutanyl in presence of thioxanthone (TXO) and ethyl acetate, under blue LED irradiation; and b4) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0138] A particular molecule is selected in a group consisting of:

[0139] - Methyl 3 -((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3 -phenylcyclobutane- 1- carboxylate (6a); - Methyl 3-((bis(4-fluorophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6b);

[0140] Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6c anti);

[0141] Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6c syn);

[0142] Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6d anti)

[0143] Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6d syn);

[0144] - Methyl-3-((di-p-tolylmethylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3-phenylcyclobutane- 1 -carboxylate (6e);

[0145] Methyl-3-((bis(4-methoxyphenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6f);

[0146] - Methyl 3 -((9 / / - fl uoren-9-ylidene)amino)- l -(pentafl uoro-X6-siilfaneyl )-3 -phenyl cyclobutane- 1 -carboxylate (6g);

[0147] - Methyl (Z)-3-(((2-methoxyphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)- 3 -phenyl cy cl obutane- 1 -carb oxy 1 ate (6h) ;

[0148] - Methyl 3-(((3,4-dimethylphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6i);

[0149] Methyl 3 -(((4-bromophenyl)(phenyl)methylene)amino)- 1 -(pentafl uoro-X6-sul faneyl )-3 - phenylcyclobutane- 1 -carboxylate (6j );

[0150] Methyl-3-(((2-methoxyphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6k);

[0151] Methyl 3-(((4-nitrophenyl)(phenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (61);

[0152] Methyl l-(pentafluoro-k6-sulfaneyl)-3-phenyl-3-((phenyl(pyridin-3- yl)methylene)amino)cy cl obutane- 1 -carboxylate (6m);

[0153] Methyl-3-((diphenylmethylene)amino)-3 -(3 -fluorophenyl)- l-(pentafluoro-X.6- sulfaneyl)cy cl obutane- 1 -carboxylate (6al );

[0154] Methyl-3-(4-chlorophenyl)-3-((diphenylmethylene)amino)-l-(pentafluoro-X.6- sulfaneyl)cy cl obutane- 1 -carboxylate (6a2);

[0155] Methyl-3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-(4-

[0156] (trifluoromethyl)phenyl)cyclobutane-l -carboxylate (6a3); and - Methyl-3-((diphenylmethylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3-(3- (trifluoromethyl)phenyl)cyclobutane-l -carboxylate (6a4).

[0157] DETAILED DESCRIPTION OF THE INVENTION

[0158] Definitions

[0159] According to the present invention, the terms below have the following meanings:

[0160] The terms mentioned herein with prefixes such as for example C1-C24 or Ci-Ce, can also be used with lower numbers of carbon atoms such as C1-C2. . If, for example, the term C1-C24 is used, it means that the corresponding hydrocarbon chain may comprise from 1 to 24 carbon atoms. If, for example, the term Ci-Ce is used, it means that the corresponding hydrocarbon chain may comprise from 1 to 6 carbon atoms, especially 1, 2, 3, 4, 5, or 6 carbon atoms. If, for example, the term C1-C3 is used, it means that the corresponding hydrocarbon chain may comprise from 1 to 3 carbon atoms, especially 1, 2, or 3 carbon atoms.

[0161] The term “alkyl” refers to a saturated, linear or branched aliphatic group. The term “(Ci- C6)alkyl” more specifically means methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, or hexyl.

[0162] The term “alkenyl” refers to an unsaturated, linear or branched aliphatic group comprising at least one carbon-carbon double bound. The term “(C2-C6)alkenyl” more specifically means ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, or hexenyl.

[0163] The term “alkynyl” refers to an unsaturated, linear or branched aliphatic group comprising at least one carbon-carbon triple bound. The term “(C2-C6)alkynyl” more specifically means ethynyl, propynyl, isopropynyl, butynyl, isobutynyl, pentynyl, or hexynyl

[0164] The term “alkoxy” or “alkyloxy” corresponds to the alkyl group as above defined bonded to the molecule by an -O- (ether) bond. (Ci-Ce)alkoxy or (Ci-Ce)alkyloxy includes methoxy or methyloxy, ethoxy or ethyloxy, propoxy or propyloxy, isopropoxy or isopropyloxy, butoxy or butyloxy, isobutoxy or isobutyloxy, pentoxy or pentyloxy, isopentoxy or isopentyloxy, and hexoxy or hexyl oxy.

[0165] The term “3-14 membered ring” corresponds to a ring having between 3 and 14 atoms. Such a term includes, for instance, the term “5-14 membered ring” having between 5 and 14 atoms, and the term “5-7 membered ring” having between 5 and 7 atoms. The term “ring” corresponds to a mono-, bi, or tricycle, which can be saturated, partially unsaturated or unsaturated, and optionally comprises at least one heteroatom. Particularly, the term “ring” includes a cycloalkyl, a heterocycloalkyl, an aryl, and a heteroaryl.

[0166] The term “cycloalkyl” corresponds to a saturated, partially unsaturated or unsaturated mono-, bi- or tri-cyclic alkyl group comprising between 3 and 14, between 5 and 14, preferably between 3 and 10 atoms of carbons. It also includes fused, bridged, or spiro-connected cycloalkyl groups. The term “cycloalkyl” includes for instance cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantanyl.

[0167] The term “heterocycloalkyl” corresponds to a saturated, partially unsaturated or unsaturated cycloalkyl group as above defined further comprising at least one heteroatom such as nitrogen (N-heterocycloalkyl), oxygen (O-heterocycloalkyl), or sulphur atom (S-heterocycloalkyl). It also includes fused, bridged, or spiro-connected heterocycloalkyl groups. Representative heterocycloalkyl groups include, but are not limited to dioxolanyl, benzo [1,3] dioxolyl, azetidinyl, oxetanyl, thiomorpholinyl, pyrazolidinyl, piperidyl, piperazinyl, 1,4-dioxanyl, pyrrolinyl, pyrrolidinyl, piperidinyl, imidazolidinyl, morpholinyl, 1,4-dithianyl, pyrrolidinyl, oxozolinyl, oxazolidinyl, isoxazolinyl, isoxazolidinyl, thiazolinyl, thiazolidinyl, isothiazolinyl, isothiazolidinyl, tetrahydropyranyl, tetrahydrofuranyl, and tetrahydrothiophenyl.

[0168] "Cycloalkyl" and "heterocycloalkyl" also include cycloalkenyl and heterocycloalkenyl which correspond respectively to a partially unsaturated cycloalkyl and a partially unsaturated heterocycloalkyl such as cyclohexenyl, imidazolinyl, dihydropyranyl, for instance 3,6-dihydro- 2H-pyranyl and 3,4-dihydro-2H-pyranyl, pyrazolinyl, azetinyl, pyranyl, and tetrahydropyridinyl, for instance 1,2,3-6-tetrahydropyridinyl, .

[0169] The term “aryl” corresponds to a mono- or bi-cyclic aromatic hydrocarbons having from 6 to 12 carbon atoms. For instance, the term “aryl” includes phenyl, biphenyl, naphthyl and anthracenyl. In a particular embodiment, the aryl is a phenyl.

[0170] The term “heteroaryl” as used herein corresponds to an aromatic, mono- or poly-cyclic group comprising between 3 and 20 atoms and comprising at least one heteroatom such as nitrogen, oxygen or sulphur atom. As used herein, the term “heteroaryl” further includes the “fused arylheterocycloalkyl” and “fused heteroarylcycloalkyl”. The terms “fused arylheterocycloalkyl” and “fused heteroarylcycloalkyl” correspond to a bicyclic group in which an aryl as above defined or a heteroaryl is respectively bounded to the heterocycloalkyl or the cycloalkyl as above defined by at least two carbons. In other terms, the aryl or the heteroaryl shares a carbon bond with the heterocycloalkyl or the cycloalkyl. Examples of such mono- and poly-cyclic heteroaryl group, fused arylheterocycloalkyl and fused arylcycloalkyl may be: pyridinyl, thiophenyl, furanyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, tetrazolyl, benzofuranyl, thianaphthal enyl, indolyl, indolinyl, indanyl, quinolinyl, isoquinolinyl, benzimidazolyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, triazinyl, thianthrenyl, benzofuranyl, dihydrobenzofuranyl, isobenzofuranyl, benzothiophenyl, isobenzothiophenyl, chromenyl, xanthenyl, phenoxanthinyl, pyrazinyl, pyridazinyl, indolizinyl, isoindolyl, indazolyl, purinyl, quinolizinyl, phtalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, P-carbolinyl, phenanthridinyl, acridinyl, pyrimidinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, furazanyl, phenoxazinyl, isochromanyl, chromanyl, imidazolidinyl, imidazolinyl, pyrazolidinyl, pyrazolinyl, indolinyl, isoindolinyl, oxazolidinyl, benzotriazolyl, benzoisoxazolyl, oxindolyl, benzoxazolyl, benzoxazolinyl, benzoxazinyl, benzothienyl, benzothiazolyl, benzodiazepinyl, benzazepinyl, benzoxazepinyl, isatinyl, dihydrobenzodi oxepinyl, dihydropyridyl, pyrimidinyl, s-triazinyl, oxazolyl, or thiofuranyl. A fused arylheterocycloalkyl is for instance an indolinyl (phenyl fused to a pyrrolidinyl) and a dihydrobenzofuranyl (phenyl fused to a dihydrofuranyl).

[0171] The term “halogen” corresponds to a fluorine, chlorine, bromine, or iodine atom.

[0172] The expression “substituted by at least” means that the radical is substituted by one or several groups of the list. For instance, the expression “a (Ci-Ce)alkyl substituted by at least one halogen, preferably a fluorine” may include a fluoromethyl (-CH2F), a difluoromethyl (-CHF2), or a trifluoromethyl (-CF3).

[0173] The expression “optionally substituted” means that the radical is not substituted or substituted by one or several groups of the list.

[0174] The “stereoisomers” are isomeric compounds that have the same molecular formula and sequence of bonded atoms, but differ in the 3D-dimensional orientations of their atoms in space. The stereoisomers include enantiomers, diastereoisomers, cis-trans and E-Z isomers, conformers, and anomers. In a particular embodiment of the invention, the stereoisomers include diastereoisomers and enantiomers.

[0175] The “tautomers” are isomeric compounds that differ only in the position of the protons and the electrons.

[0176] The “hydrates” are compounds further comprising at least one molecule of water. For instance, if the compound comprises one molecule of water, it corresponds to a monohydrate form. If the compound comprises two molecules of water, it corresponds to a dihydrate form.

[0177] The “salts” include inorganic as well as organic acids salts. Representative examples of suitable inorganic acids include hydrochloric, hydrobromic, hydroiodic, phosphoric, and the like. Representative examples of suitable organic acids include formic, acetic, trichloroacetic, trifluoroacetic, propionic, benzoic, cinnamic, citric, fumaric, maleic, methanesulfonic and the like. Further examples of inorganic or organic acid addition salts include the pharmaceutically salts listed in J. Pharm. Sci. 1977, 66, 2, and in Handbook of Pharmaceutical Salts: Properties, Selection, and Use edited by P. Heinrich Stahl and Camille G. Wermuth 2002. In a particular embodiment, the salt is selected from the group consisting of maleate, chlorhydrate, bromhydrate, and methanesulfonate. The “salts” also include inorganic as well as organic base salts. Representative examples of suitable inorganic bases include sodium or potassium salt, an alkaline earth metal salt, such as a calcium or magnesium salt, or an ammonium salt.

[0178] As used herein, the term “molecule” in the expression “a molecule comprising a pentafluorosulfanyl (SFs) group” includes any molecule substituted by at least one SFs group. Particularly, this molecule is a molecule, a compound, or an ingredient of interest in various fields, such as pharmaceuticals, agrochemicals, cosmetics, and materials. In a particular embodiment, the SFs-substituted molecule is a pharmaceutical that includes the terms "active principle", "active ingredient", “bioactive ingredient” "active pharmaceutical ingredient", “medicine”, and “drug”. These terms are equivalents and refer to a compound having a therapeutic effect.

[0179] As used herein, the term “molecule” in the expression “a molecule comprising a styrene unit” includes any molecule having a styrene unit or substituted by a styrene unit, “a molecule comprising a styrene unit” may have the following motif R-CH=CH2 in which R can be any chemical groups or any chemical structures having an interest in various fields including, for instance, pharmaceuticals, agrochemicals, cosmetics, and materials. In a particular embodiment, R is a phenyl optionally substituted by any substituents, such as for instance, a halogen, a (Ci- Ce)alkyl, a (Ci-Ce)alkyloxy, and any other groups or radicals.

[0180] As used herein, the term “molecule” in the expression “a molecule comprising an azabicyclobutanyl” includes any molecule having an azabicyclobutanyl group or substituted by an azabicyclobutanyl group, “a molecule comprising an azabicyclobutanyl” may have the following formula (A): which R? is a radical selected in a group consisting of a phenyl, a phenyl substituted by a (Ci-Ce)alkyl optionally substituted by at least one halogen, and a CO-phenyl; and Rs is a radical selected in a group consisting of a hydrogen, and a (Ci-Ce)alkyl. As used herein, the term “molecule” in the expression “a molecule comprising a bicyclobutanyl” includes any molecule having a bicyclobutanyl group or substituted by a bicyclobutanyl group, “a molecule comprising a bicyclobutanyl” may have the following formula (B): in which R9 is a radical selected in a group consisting of a phenyl and a phenyl substituted by a halogen or a (Ci-Ce)alkyl optionally substituted by at least one halogen.

[0181] The present invention provides a compound of formula (I), (II), or (III): wherein: Ri and R2, R3 and R4, and Rs and Re represent independently a radical selected in a group consisting of:

[0182] • a hydrogen,

[0183] • a radical selected in a group consisting of a (Ci-Ce)alkyl, and a 5-14 membered ring, said radical is optionally substituted by at least one radical selected in a group consisting of: a halogen,

[0184] - a (Ci-Ce)alkyl, a (Ci-Ce)alkyloxy, a nitro,

[0185] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), and

[0186] • a CO-O-Ra or a CO-Rb with Ra and Rb represent independently a radical selected in a group consisting of: a (Ci-Ci2)alkyl optionally substituted by a (C2-Cn)alkynyl or by a 5- 14 membered ring optionally substituted by a (Ci-Ce)alkyl, and and a 5-14 membered ring optionally substituted a (Ci-C24)alkyl; or Ri and R2, R3 and R4, and Rs and Re may form together a 5-14 membered ring optionally substituted by a radical selected in a group consisting of:

[0187] • a halogen, • a (Ci-Ce)alkyl,

[0188] • a (Ci-Ce)alkyloxy,

[0189] • a nitro,

[0190] • a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and

[0191] • a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), with the proviso that when one of Ri and R2 is a hydrogen, then the other is not a hydrogen; when one of R3 and R4 is a hydrogen, then the other is not a hydrogen, and when one of Rs and Re is a hydrogen, then the other is not a hydrogen; and the stereoisomers, and the salts thereof.

[0192] Imine series

[0193] In an embodiment, the compound of the invention is a compound of formula (I), with Ri and R2 are such as defined herein. The compounds of the invention having the formula (I) are also called herein the “imine series”.

[0194] An object of the invention is therefore a compound of formula (I): wherein: Ri and R2 represent independently a radical selected in a group consisting of:

[0195] • a hydrogen,

[0196] • a radical selected in a group consisting of a (Ci-Ce)alkyl, and a 5-14 membered ring, said radical is optionally substituted by at least one radical selected in a group consisting of: a halogen,

[0197] - a (Ci-Ce)alkyl, a (Ci-Ce)alkyloxy, a nitro,

[0198] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), and • a CO-O-Ra or a CO-Rb with Ra and Rb represent independently a radical selected in a group consisting of: a (Ci-Ci2)alkyl optionally substituted by a (C2-Ci2)alkynyl or by a 5- 14 membered ring optionally substituted by a (Ci-Ce)alkyl, and and a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl; or Ri and R2 may form together a 5-14 membered ring optionally substituted by a radical selected in a group consisting of:

[0199] • a halogen,

[0200] • a (Ci-Ce)alkyl,

[0201] • a (Ci-Ce)alkyloxy,

[0202] • a nitro,

[0203] • a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and

[0204] • a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), with the proviso that when one of Ri and R2 is a hydrogen, then the other is not a hydrogen; and the stereoisomers, and the salts thereof.

[0205] A further object of the invention is a process for preparing a compound of formula (I) with Ri and R2 are such as defined herein, comprising the following steps of: a) reacting pentafluorosulfanyldi chloramine (SF5NCI2) with a compound of formula (I’) with Y represents N2 or O, and

[0206] Ri and R2 are such as defined in any one of claims 1 to 6 ; and b) recovering said compound of formula (I). In a preferred embodiment, the compound of formula (I) is such that Y represents N2.

[0207] Pentafluorosulfanyldichloramine can be purchased from any commercial suppliers or can be also prepared.

[0208] In an embodiment, pentafluorosulfanyldichloramine is prepared by a process comprising the following steps of aOl) reacting 2,3,4,5,6-pentafluorobenzamide with octasulfur (Ss), trichloroisocyanuric acid, and tetrabutylammonium chloride in acetonitrile; a02) adding AgF2 powder to the mixture of step aOl); a03) adding a mixture comprising trichloroisocyanuric acid and potassium fluoride in acetonitrile in the mixture of step a02); and a04) recovering pentafluorosulfanyldichloramine (SF5NCI2).

[0209] In a particular embodiment, pentafluorosulfanyldichloramine is recovered by an evaporation step and then reacted with a compound of formula (F) in step a).

[0210] Alternatively, pentafluorosulfanyldichloramine obtained at step a03) is not recovered or isolated and is directly reacted with a compound of formula (F) in step a).

[0211] A further object of the invention is a process for preparing a compound of formula (I) with Ri and R2 are such as defined herein, comprising the following steps of aOl) reacting 2,3,4,5,6-pentafluorobenzamide with octasulfur (Ss), trichloroisocyanuric acid, and tetrabutylammonium chloride in acetonitrile; a02) adding AgF2 powder to the mixture of step aOl); a03) adding a mixture comprising trichloroisocyanuric acid and potassium fluoride in acetonitrile in the mixture of step a02); and a) adding a compound of formula (I’) with Y represents N2 or O, and Ri and R2 are such as defined herein to the mixture of step a03); and b) recovering the compound of formula (I).

[0212] In a particular embodiment, the step aOl) is performed at a temperature between 25 °C and 60 °C, preferably about 40 °C. In a further particular embodiment, the step aOl) is performed from 1 to 12 hours, preferably from 2 to 6 hours, more preferably about 4 hours.

[0213] In a particular embodiment, 5 equivalents of AgF2 powder relative to 2, 3, 4,5,6- pentafluorobenzamide is used at step a02).

[0214] In a particular embodiment, the step a03) is performed at a temperature between -30 °C and - 10 °C, preferably about -15 °C. In a further particular embodiment, the step a03) is performed from 12 hours to 36 hours, preferably from 20 to 28 hours, more preferably about 24 hours.

[0215] In a particular embodiment, the step a) is performed in a mixture of dichloromethane and hexane. In a further particular embodiment, the step a) is performed at a temperature between 25 °C and 60 °C, preferably about 40 °C. In a further particular embodiment, the step a) is performed from 1 to 16 hours, preferably from 2 to 12 hours.

[0216] An object of the invention is thus a process for preparing a compound of formula (I): wherein: Ri and R2 represent independently a radical selected in a group consisting of

[0217] • a hydrogen,

[0218] • a radical selected in a group consisting of a (Ci-Ce)alkyl, and a 5-14 membered ring, said radical is optionally substituted by at least one radical selected in a group consisting of a halogen, a (Ci-Ce)alkyl, a (Ci-Ce)alkyloxy, a nitro,

[0219] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), and

[0220] • a CO-O-Ra or a CO-Rb with Ra and Rb represent independently a radical selected in a group consisting of: a (Ci-Ci2)alkyl optionally substituted by a (C2-Cn)alkynyl or by a 5- 14 membered ring optionally substituted by a (Ci-Ce)alkyl, and and a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl; or Ri and R2 may form together a 5-14 membered ring optionally substituted by a radical selected in a group consisting of:

[0221] • a halogen,

[0222] • a (Ci-Ce)alkyl,

[0223] • a (Ci-Ce)alkyloxy,

[0224] • a nitro,

[0225] • a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and

[0226] • a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), with the proviso that when one of Ri and R2 is a hydrogen, then the other is not a hydrogen; and the stereoisomers, and the salts thereof; comprising the following steps of: a) reacting pentafluorosulfanyldichloramine (SF5NCI2) with a compound of formula (I’): with Y represents N2 or O, and

[0227] Ri and R2 are such as defined herein; and b) recovering said compound of formula (I).

[0228] In a particular embodiment, Ri represents a 5-14 membered ring optionally substituted by a radical selected in a group consisting of a bromine, a chorine, a fluorine, a methyl, a methoxy, a nitro, a CO-O-methyl. More specifically, Ri represents a phenyl optionally substituted by a radical selected in a group consisting of a bromine, a chorine, a fluorine, a methyl, a methoxy, a nitro, a C0-0-m ethyl.

[0229] In a particular embodiment, R2 represents a 5-14 membered ring optionally substituted by at least one radical selected in a group consisting of:

[0230] - a halogen, preferably a fluorine, a bromine, or a chlorine,

[0231] - a (Ci-Ce)alkyl, preferably a methyl,

[0232] - a (Ci-Ce)alkyloxy, preferably a methoxy,

[0233] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, preferably a O-C(CH3)2-CO-O-CH(CH3)2, and

[0234] - a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), preferably a CH(CH3)-CO-O- (adamantanyl).

[0235] More specifically, R2 represents a 5-14 membered ring selected in a group consisting of an aryl, preferably a phenyl, and a heteroaryl, preferably a pyridinyl, said 5-14 membered ring is optionally substituted by at least one radical selected in a group consisting of:

[0236] - a halogen, preferably a fluorine, a bromine, or a chlorine,

[0237] - a (Ci-Ce)alkyl, preferably a methyl,

[0238] - a (Ci-Ce)alkyloxy, preferably a methoxy,

[0239] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, preferably a O-C(CH3)2-CO-O-CH(CH3)2, and

[0240] - a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), preferably a CH(CH3)-CO-O- (adamantanyl).

[0241] In a further particular embodiment, R2 represents a CO-O-Ra or a CO-Rb, with Raand Rb represent independently a radical selected in a group consisting of:

[0242] - a (Ci-Ci2)alkyl optionally substituted by a radical selected in a group consisting of a (C2-Cn)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and

[0243] - a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl.

[0244] In a more particular embodiment, R2 represents a CO-O-Ra with Ra represents a radical selected in a group consisting of:

[0245] - a (Ci-Ci2)alkyl optionally substituted by a radical selected in a group consisting of a a (C2-Cn)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and

[0246] - a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl. Preferably, Ra represents a radical selected in a group consisting of a methyl, an ethyl, an hexyl, an isobutyl, a 2-methylbutyl, a 2-methylbut-3-yn-2yl, a tetrahydrofuranyl, a cyclohexyl, a 2- isopropyl-5-methylcyclohexyl, a 2-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl, an adamantanyl, a 2,2,7,7-tetramethyltetrahydro-5H-bis([l,3]dioxole)[4,5-b:4’,5’-d]pyran-5- yl)methyl, a phenyl, and a tetramethyl-2-(4,8,12-trimethyltridecyl)-chroman-6-yl.

[0247] In a further more particular embodiment, R2 represents a CO-Rb, with Rb represents a radical selected in a group consisting of:

[0248] - a (Ci-Ci2)alkyl optionally substituted by a radical selected in a group consisting of a a (C2-Ci2)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and

[0249] - a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl.

[0250] Preferably, Rb represents a phenyl.

[0251] A preferred compound of formula (I) is a compound selected in a group consisting of:

[0252] - N-(pentafluoro-Z6-sulfaneyl)-l,l-diphenylmethanimine (2a);

[0253] - l,l-Bis(4-fluorophenyl)-N-(pentafluoro-Z6-sulfaneyl)methanimine (2b);

[0254] - l,l-Bis(4-bromophenyl)-N-(pentafluoro-Z6-sulfaneyl)methanimine (2c);

[0255] - l , l -Bis(4-chlorophenyl)-N-(pentafluoro-k6-sulfaneyl)methanimine (2d);

[0256] - N-(pentafluoro-A6-sulfaneyl)- l , l -di-p-tolylmethanimine (2e);

[0257] - 1,1 -Bi s(4-methoxyphenyl )-N-(pentafluoro-k6-sulfaneyl )methanimine (2f);

[0258] - N-(pentafluoro-k6-sulfaneyl)-9H-fluoren-9-imine (2g);

[0259] - (Z)-l -(naphthal en-2-yl )-N-(pentafluoro-k6-sulfaneyl )- l -phenyl methani mine (2h);

[0260] - (E)- 1 -(4-nitrophenyl)-N-(pentafluoro-Z6-sulfaneyl)- 1 -phenylmethanimine (2i);

[0261] - (E)-l -(3, 4-dimethylphenyl)-N-(pentafluoro-Z6-sulfaneyl)-l -phenylmethanimine (2j);

[0262] - (E)-l-(2-methoxyphenyl)-N-(pentafluoro-Z6-sulfaneyl)-l -phenylmethanimine (2k);

[0263] - (Z)-N-(pentafluoro-Z6-sulfaneyl)-l -phenyl- l-(pyri din-3 -yl)methanimine (21);

[0264] - (E)- 1 -(4-bromophenyl)-N-(pentafluoro-Z6-sulfaneyl)- 1 -phenylmethanimine (2m);

[0265] - Isopropyl (E)-2-(4-((4-chlorophenyl)((pentafluoro-Z6-sulfaneyl)imino)methyl)phenoxy)-2- methylpropanoate (2n);

[0266] (lR,3S,5r,7r)-Adamantan-2-yl 2-(3-((Z)-((pentafluoro-Z6- sulfaneyl)imino)(phenyl)methyl)phenyl)propanoate (2o);

[0267] - Ethyl (Z)-2-((pentafluoro-Z6-sulfaneyl)imino)-2-phenylacetate (2p);

[0268] - Ethyl (Z)-2-(4-bromophenyl)-2-((pentafluoro-Z6-sulfaneyl)imino)acetate (2q);

[0269] - Ethyl (Z)-2-(4-nitrophenyl)-2-((pentafluoro-Z6-sulfaneyl)imino)acetate (2r); - Methyl (Z)-4-(2-methoxy-2-oxo-l-((pentafluoro-X6-sulfaneyl)imino)ethyl)benzoate (2s);

[0270] - Ethyl (Z)-2-(4-methoxyphenyl)-2-((pentafluoro-X6-sulfaneyl)imino)acetate (2t);

[0271] - Ethyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-(o-tolyl)acetate (2u);

[0272] - Hexyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2v);

[0273] - Isobutyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2w);

[0274] - (S)-2-Methylbutyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2x);

[0275] - 2-Methylbut-3-yn-2-yl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2y);

[0276] - Tetrahydrofuran-3-yl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2z);

[0277] - Cyclohexyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2aa);

[0278] (2R,5S)-2-Isopropyl-5-methylcyclohexyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2- phenylacetate (2ab);

[0279] 2-((lR,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl (Z)-2-((pentafluoro-X6- sulfaneyl)imino)-2-phenylacetate (2ac);

[0280] - (lr,3r,5r,7r)-Adamantan-2-yl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2ad);

[0281] ((3aS,5S,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2ae);

[0282] - Phenyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2af);

[0283] (S)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl (Z)-2-

[0284] ((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2ag); and

[0285] - (Z)-2-((pentafluoro-X6-sulfaneyl)imino)- 1 ,2-Diphenylethan- 1 -one (2ah).

[0286] Amine series

[0287] In an embodiment, the compound of the invention is a compound of formula (II) or (III), with R3 and R4 or Rs and Re are such as defined herein. The compounds of the invention having the formula (II) or (III) are also called herein the “amine series”.

[0288] An object of the invention is therefore a compound of formula (II): wherein: R.3 and R4 represent independently a radical selected in a group consisting of: • a hydrogen,

[0289] • a radical selected in a group consisting of a (Ci-Ce)alkyl, and a 5-14 membered ring, said radical is optionally substituted by at least one radical selected in a group consisting of: a halogen,

[0290] - a (Ci-Ce)alkyl, a (Ci-Ce)alkyloxy, a nitro,

[0291] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), and

[0292] • a CO-O-Ra or a CO-Rb with Ra and Rb represent independently a radical selected in a group consisting of: a (Ci-Ci2)alkyl optionally substituted by a (C2-Ci2)alkynyl or by a 5- 14 membered ring optionally substituted by a (Ci-Ce)alkyl, and and a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl; or a and R4 may form together a 5-14 membered ring optionally substituted by a radical selected in a group consisting of:

[0293] • a halogen,

[0294] • a (Ci-Ce)alkyl,

[0295] • a (Ci-Ce)alkyloxy,

[0296] • a nitro,

[0297] • a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and

[0298] • a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), with the proviso that when one of R3 and R4 is a hydrogen, then the other is not a hydrogen; and the stereoisomers, and the salts thereof.

[0299] In a particular embodiment, R3 represents a 5-14 membered ring optionally substituted by a radical selected in a group consisting of a bromine, a chorine, a fluorine, a methyl, a methoxy, a nitro, a CO-O-methyl. More specifically, R3 represents a phenyl optionally substituted by a radical selected in a group consisting of a bromine, a chorine, a fluorine, a methyl, a methoxy, a nitro, a CO-O-methyl. In a particular embodiment, R4 represents a 5-14 membered ring optionally substituted by at least one radical selected in a group consisting of:

[0300] - a halogen, preferably a fluorine, a bromine, or a chlorine,

[0301] - a (Ci-Ce)alkyl, preferably a methyl,

[0302] - a (Ci-Ce)alkyloxy, preferably a methoxy,

[0303] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, preferably a O-C(CH3)2-CO-O-CH(CH3)2, and

[0304] - a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), preferably a CH(CH3)-CO-O- (adamantanyl).

[0305] More specifically, R4 represents a 5-14 membered ring selected in a group consisting of an aryl, preferably a phenyl, and a heteroaryl, preferably a pyridinyl, said 5-14 membered ring is optionally substituted by at least one radical selected in a group consisting of:

[0306] - a halogen, preferably a fluorine, a bromine, or a chlorine,

[0307] - a (Ci-Ce)alkyl, preferably a methyl,

[0308] - a (Ci-Ce)alkyloxy, preferably a methoxy,

[0309] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, preferably a O-C(CH3)2-CO-O-CH(CH3)2, and

[0310] - a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), preferably a CH(CH3)-CO-O- (adamantanyl).

[0311] In a further particular embodiment, R4 represents a CO-O-Ra or a CO-Rb, with Raand Rb represent independently a radical selected in a group consisting of:

[0312] - a (Ci-Ci2)alkyl optionally substituted by a radical selected in a group consisting of a (C2-Cn)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and

[0313] - a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl.

[0314] In a more particular embodiment, R4 represents a CO-O-Ra with Ra represents a radical selected in a group consisting of:

[0315] - a (Ci-Ci2)alkyl optionally substituted by a radical selected in a group consisting of a (C2-Cn)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and

[0316] - a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl.

[0317] Preferably, Ra represents a radical selected in a group consisting of a methyl, an ethyl, an hexyl, an isobutyl, a 2-methylbutyl, a 2-methylbut-3-yn-2yl, a tetrahydrofuranyl, a cyclohexyl, a 2- isopropyl-5-methylcyclohexyl, a 2-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl, an adamantanyl, a 2,2,7,7-tetramethyltetrahydro-5H-bis([l,3]dioxole)[4,5-b:4’,5’-d]pyran-5- yl)methyl, a phenyl, and a tetramethyl-2-(4,8,12-trimethyltridecyl)-chroman-6-yl.

[0318] In a further more particular embodiment, R4 represents a CO-Rb, with Rb represents a radical selected in a group consisting of:

[0319] - a (Ci-Ci2)alkyl optionally substituted by a radical selected in a group consisting of a a (C2-Ci2)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and

[0320] - a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl.

[0321] Preferably, Rb represents a phenyl.

[0322] A further object of the invention is a process for preparing a compound of formula (II)

[0323] SF5

[0324] / N\ R3 R4 (n), with R3 and R4 are such as defined herein, comprising the following steps of: a) reacting pentafluorosulfanyl dichloramine (SF5NCI2) with a compound of formula (II’): R3- Z (II’) and / or a compound of formula (II”): R4-Z (II”) with R3 and R4 are such as defined herein, and

[0325] Z represents MgX with X is a halogen, Li, or B(0H)2; and b) recovering said compound of formula (II).

[0326] Another object of the invention is also a compound of formula (III): wherein: Rs and Re represent independently a radical selected in a group consisting of:

[0327] • a hydrogen,

[0328] • a radical selected in a group consisting of a (Ci-Ce)alkyl, and a 5-14 membered ring, said radical is optionally substituted by at least one radical selected in a group consisting of: a halogen,

[0329] - a (Ci-Ce)alkyl, a (Ci-Ce)alkyloxy, a nitro,

[0330] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), and

[0331] • a CO-O-Ra or a CO-Rb with Ra and Rb represent independently a radical selected in a group consisting of: a (Ci-Ci2)alkyl optionally substituted by a (C2-Ci2)alkynyl or by a 5- 14 membered ring optionally substituted by a (Ci-Ce)alkyl, and and a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl; or Rs and Re may form together a 5-14 membered ring optionally substituted by a radical selected in a group consisting of:

[0332] • a halogen,

[0333] • a (Ci-Ce)alkyl,

[0334] • a (Ci-Ce)alkyloxy,

[0335] • a nitro,

[0336] • a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and

[0337] • a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), with the proviso that when one of Rs and Re is a hydrogen, then the other is not a hydrogen; and the stereoisomers, and the salts thereof.

[0338] In a particular embodiment, Rs represents a 5-14 membered ring optionally substituted by a radical selected in a group consisting of a bromine, a chorine, a fluorine, a methyl, a methoxy, a nitro, a CO-O-methyl. More specifically, Rs represents a phenyl optionally substituted by a radical selected in a group consisting of a bromine, a chorine, a fluorine, a methyl, a methoxy, a nitro, a CO-O-methyl.

[0339] In a particular embodiment, Re represents a 5-14 membered ring optionally substituted by at least one radical selected in a group consisting of:

[0340] - a halogen, preferably a fluorine, a bromine, or a chlorine, - a (Ci-Ce)alkyl, preferably a methyl,

[0341] - a (Ci-Ce)alkyloxy, preferably a methoxy,

[0342] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, preferably a O-C(CH3)2-CO-O-CH(CH3)2, and

[0343] - a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), preferably a CH(CH3)-CO-O- (adamantanyl).

[0344] More specifically, Re represents a 5-14 membered ring selected in a group consisting of an aryl, preferably a phenyl, and a heteroaryl, preferably a pyridinyl, said 5-14 membered ring is optionally substituted by at least one radical selected in a group consisting of:

[0345] - a halogen, preferably a fluorine, a bromine, or a chlorine,

[0346] - a (Ci-Ce)alkyl, preferably a methyl,

[0347] - a (Ci-Ce)alkyloxy, preferably a methoxy,

[0348] - a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, preferably a O-C(CH3)2-CO-O-CH(CH3)2, and

[0349] - a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), preferably a CH(CH3)-CO-O- (adamantanyl).

[0350] In a further particular embodiment, Re represents a CO-O-Ra or a CO-Rb, with Raand Rb represent independently a radical selected in a group consisting of:

[0351] - a (Ci-Ci2)alkyl optionally substituted by a radical selected by a (C2-Cn)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and

[0352] - a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl.

[0353] In a more particular embodiment, Re represents a CO-O-Ra with Ra represents a radical selected in a group consisting of:

[0354] - a (Ci-Ci2)alkyl optionally substituted by a radical selected by a (C2-Cn)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and

[0355] - a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl.

[0356] Preferably, Ra represents a radical selected in a group consisting of a methyl, an ethyl, an hexyl, an isobutyl, a 2-methylbutyl, a 2-methylbut-3-yn-2yl, a tetrahydrofuranyl, a cyclohexyl, a 2- isopropyl-5-methylcyclohexyl, a 2-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl, an adamantanyl, a 2,2,7,7-tetramethyltetrahydro-5H-bis([l,3]dioxole)[4,5-b:4’,5’-d]pyran-5- yl)methyl, a phenyl, and a tetramethyl-2-(4,8,12-trimethyltridecyl)-chroman-6-yl.

[0357] In a further more particular embodiment, Re represents a CO-Rb, with Rb represents a radical selected in a group consisting of:

[0358] - a (Ci-Ci2)alkyl optionally substituted by a radical selected by a (C2-Cn)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and - a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl.

[0359] Preferably, Rb represents a phenyl.

[0360] A further object of the invention is a process for preparing a compound of formula (III), with Rs and Re are such as defined herein, comprising the following steps of: a) reacting pentafluorosulfanyldi chloramine (SF5NCI2) with a compound of formula (III’): Rs- Z (III’) and / or a compound of formula (III”): Re-Z (III”), with Rs, and Re are such as defined herein, and

[0361] Z represents MgX with X is a halogen, Li, or B(OH)2; and b) recovering said compound of formula (III).

[0362] As above described, pentafluorosulfanyldichloramine can be purchased from any commercial suppliers or can be also prepared by any methods or processes, such as the process comprising the following steps aOl), a02), a03), and a04) as disclosed herein.

[0363] A further object of the invention is also a process for preparing a compound of formula (II) or (III), with R3, R4, Rs, and Re are such as defined herein, comprising the following steps of: aOl) reacting 2,3,4,5,6-pentafluorobenzamide with octasulfur (Ss), trichloroisocyanuric acid, and tetrabutylammonium chloride in acetonitrile; a02) adding AgF2 powder to the mixture of step aOl); a03) adding a mixture comprising trichloroisocyanuric acid and potassium fluoride in acetonitrile in the mixture of step a02); a) reacting pentafluorosulfanyl dichloramine (SF5NCI2) with a compound of formula (II’): R3- Z (IF) and / or a compound of formula (II”): R4-Z (II”); or reacting pentafluorosulfanyldichloramine (SF5NCI2) with a compound of formula (III’): Rs-Z (III’) and / or a compound of formula (III”): Re-Z (III”), with

[0364] R3, R4, Rs, and Re are such as defined in claim 1, and

[0365] Z represents MgX with X is a halogen, Li, or B(OH)2; and b) recovering said compound of formula (II) or (III).

[0366] SFs-substituted molecules

[0367] The invention further provides SFs-substituted molecules obtained by methods and processes implementing the compounds of formula (I), (II), or (III) as defined herein.

[0368] An object of the invention is therefore a use of a compound of formula (I), (II), or (III) as defined herein for preparing a molecule comprising a pentafluorosulfanyl (SF5) group. An object of the invention is also a use of a compound of formula (I), (II), or (III) as defined herein for incorporating a pentafluorosulfanyl (SF5) group in a molecule.

[0369] A particular object of the invention is a use of a compound of formula (I), as defined herein for preparing a molecule comprising a pentafluorosulfanyl (SF5) group. A particular object of the invention is also a use of a compound of formula (I) as defined herein for incorporating a pentafluorosulfanyl (SF5) group in a molecule.

[0370] A more particular object of the invention is a use of a compound of formula (I), as defined herein for preparing a molecule comprising a pentafluorosulfanyl (SF5) group or for incorporating a pentafluorosulfanyl (SF5) group in a molecule, wherein said molecule is selected in a group consisting of:

[0371] - N-(2-(pentafluoro-X6-sulfaneyl)-l-(p-tolyl)ethyl)-l, 1-diphenylmethanimine (4a);

[0372] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 -(m-tolyl)ethyl)- 1 , 1 -diphenylmethanimine (4b);

[0373] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 -(o-tolyl)ethyl)- 1 , 1 -diphenylmethanimine (4c);

[0374] - N-(l-(4-(tert-butyl)phenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)-l, 1-diphenylmethanimine (4d);

[0375] - 4-( l -((di phenyl methyl ene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Phenyl acetate (4e);

[0376] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 -phenylethyl)- 1 , 1 -diphenylmethanimine (4f);

[0377] - N-( 1 -(naphthal en-2-yl )-2-(pentafl uoro-X6-sulfaneyl jethyl )- 1 , 1 -diphenylmethanimine (4g);

[0378] - N-( 1 -(4-chlorophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4h); - N-(l-(4-bromophenyl)-2-(pentafluoro-X.6-sulfaneyl)ethyl)-l, 1 -diphenylmethanimine (4i);

[0379] - N-(l-(4-iodophenyl)-2-(pentafluoro-X.6-sulfaneyl)ethyl)- 1,1 -diphenylmethanimine (4j);

[0380] - N-( 1 -([ 1 , 1 '-biphenyl]-4-yl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4k);

[0381] - 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Benzonitrile (41);

[0382] - N-( 1 -(4-nitrophenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4m);

[0383] - 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Benzaldehyde (4n);

[0384] - N-(2-(pentafluoro-X.6-sulfaneyl)- 1 , 1 -diphenylethyl)- 1 , 1 -diphenylmethanimine (4o);

[0385] - N-( 1 -(pentafluoro-k6-sulfaneyl)-2-phenylpropan-2-yl)- 1 , 1 -diphenylmethanimine (4p);

[0386] - N-(2-(pentafluoro-k6-sulfaneyl)-l-(thiophen-2-yl)ethyl)-l, 1 -diphenylmethanimine (4q);

[0387] (1 S,2R,5S)-2-isopropyl-5-methylcyclohexyl 4-(l-((diphenylmethylene)amino)-2- (pentafluoro-k6-sulfaneyl)ethyl)benzoate (4r);

[0388] ((S)-4-(prop- 1 -en-2-yl)cyclohex- 1 -en- 1 -yl)Methyl 4-( 1 -((diphenylmethylene)amino)-2-

[0389] (pentafluoro-k6-sulfaneyl)ethyl)benzoate (4s);

[0390] ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6- sulfaneyl)ethyl)benzoate (4t);

[0391] 2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(l-

[0392] ((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (4u);

[0393] (S)-3,7-dimethyloct-6-en-l-yl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6- sulfaneyl)ethyl)Benzoate (4v);

[0394] 4-Formyl-2-methoxyphenyl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (4w);

[0395] (8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,ll,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6- sulfaneyl)ethyl)benzoate (4x);

[0396] (R)-2, 5 ,7, 8-Tetramethy l-2-((4R, 8R)-4, 8, 12-trimethyltridecyl)chroman-6-yl 4-( 1 -

[0397] ((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (4y);

[0398] - (4-(tert-butyl)phenethyl)Pentafluoro-k6-sulfane (5b);

[0399] - (4-(chloromethyl)phenethyl)Pentafluoro-X6-sulfane (5e);

[0400] - Pentafluoro(4-iodophenethyl)- k6-sulfane (5h);

[0401] - (2-([l,l'-biphenyl]-4-yl)ethyl)Pentafluoro-X.6-sulfane (5j);

[0402] - (1 S,2R,5S)-2-Isopropyl-5-methylcyclohexyl 4-(2-(pentafluoro-k6-sulfaneyl)ethyl)benzoate (5k); (S)-(4-(prop- 1 -en-2-yl)cyclohex- 1 -en- 1 -yl)Methyl 4-(2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (51);

[0403] ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5m);

[0404] 2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (5n);

[0405] - (S)-3,7-Dimethyloct-6-en-l-yl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5o);

[0406] - 4-Formyl-2-methoxyphenyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5p);

[0407] (8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,l l,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5q);

[0408] - N-( l-(pentafluoro-X.6-sulfaneyl)-3 -phenylazeti din-3 -yl)- 1, 1-diphenylmethanimine (3a);

[0409] - l,l-bis(4-fluorophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3b);

[0410] - l,l-bis(4-bromophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3 c)

[0411] - l,l-bis(4-chlorophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3d);

[0412] - N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazeti din-3 -yl)-l,l-di-p-tolylmethanimine (3e); l,l-bis(4-methoxyphenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3- yl)methanimine (3f);

[0413] - 7V-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)-9JH-fluoren-9-imine (3g);

[0414] 1 -(naphthal en-2-yl)-N-(l -(pentafl uoro-A6-sulf aneyl )-3 -phenylazeti din-3 -yl)- 1 - phenylmethanimine (3h); l-(4-nitrophenyl)-N-(l-(pentafluoro-X.6-sulfaneyl)-3 -phenylazeti din-3 -yl)-l- phenylmethanimine (3i); l-(3,4-dimethylphenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3j);

[0415] 1 -(2-methoxyphenyl)-N-(l -(pentafl uoro-A6-siilf aneyl )-3 -phenylazeti din-3 -yl)- 1 - phenylmethanimine (3 k);

[0416] N-(l -(pentafl uoro-A6-sulf aneyl )-3 -phenylazeti din-3 -yl)- 1 -phenyl- 1 -(pyri din-3 - yl)methanimine (31); l-(4-bromophenyl)-N-(l-(pentafluoro-X.6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3m); 2-(4-((4-chlorophenyl)((l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3- yl)imino)methyl)phenoxy)-2-methylpropanoate (3n);

[0417] - N-( 1 -(pentafluoro-X6-sulfaneyl)-3 -(p-tolyl)azetidin-3 -yl)- 1 , 1 -diphenylmethanimine (3 a 1 );

[0418] N-( 1 -(pentafluoro-X6-sulfaneyl)-3 -(4-(trifluoromethyl)phenyl)azeti din-3 -yl)- 1,1- diphenylmethanimine (3a2);

[0419] (3-((diphenylmethylene)amino)-l-(pentafluoro-X6-sulfaneyl)azetidin-3- yl)(phenyl)methanone (3a3);

[0420] N-2-methyl- l-(pentafluoro-X6-sulfaneyl)-3-phenylazeti din-3 -yl)- 1,1 -diphenylmethanimine (3a4);

[0421] - Methyl 3 -((diphenylmethylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3 -phenylcyclobutane- 1- carboxylate (6a);

[0422] - Methyl 3-((bis(4-fluorophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6b);

[0423] Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6c anti);

[0424] Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6c syn);

[0425] Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6d anti)

[0426] Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6d syn);

[0427] - Methyl-3-((di-p-tolylmethylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3-phenylcyclobutane- 1 -carboxylate (6e);

[0428] Methyl-3-((bis(4-methoxyphenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6f);

[0429] - Methyl 3 -((9JH-fluoren-9-ylidene)amino)-l-(pentafluoro-X6-sulfaneyl)-3 -phenylcyclobutane- 1 -carboxylate (6g);

[0430] - Methyl (Z)-3-(((2-methoxyphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)- 3 -phenyl cy cl obutane- 1 -carb oxy 1 ate (6h) ;

[0431] - Methyl 3-(((3,4-dimethylphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcy cl obutane- 1 -carboxylate (6i);

[0432] Methyl 3 -(((4-bromophenyl)(phenyl)methylene)amino)- 1 -(pentafl uoro-X6-sul faneyl )-3 - phenylcyclobutane- 1 -carboxylate (6j ); Methyl-3-(((2-methoxyphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6k);

[0433] Methyl 3-(((4-nitrophenyl)(phenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (61);

[0434] Methyl l-(pentafluoro-k6-sulfaneyl)-3-phenyl-3-((phenyl(pyridin-3- yl)methylene)amino)cyclobutane- 1 -carboxylate (6m);

[0435] Methyl-3-((diphenylmethylene)amino)-3 -(3 -fluorophenyl)- l-(pentafluoro-X.6- sulfaneyl)cyclobutane- 1 -carboxylate (6al );

[0436] Methyl-3-(4-chlorophenyl)-3-((diphenylmethylene)amino)-l-(pentafluoro-X.6- sulfaneyl)cyclobutane- 1 -carboxylate (6a2);

[0437] Methyl-3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-(4- (trifluoromethyl)phenyl)cyclobutane-l -carboxylate (6a3); and

[0438] Methyl-3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-(3- (trifluoromethyl)phenyl)cyclobutane-l -carboxylate (6a4).

[0439] For preparing SFs-substituted molecules, the inventors proposed two alternatives of processes starting from a molecule comprising a styrene unit. A molecule comprising a styrene unit may be represented by the formula R-CH=CH2 (A) as above defined.

[0440] A first process is based on the reactivity of molecules (I) under energy transfer catalysis conditions.

[0441] Thus provided herein, a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: al) reacting a compound of formula (I) as defined herein with a molecule comprising a styrene unit in presence of thioxanthone (TXO) under blue LED irradiation; and bl) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0442] In a particular embodiment, the step al) is performed under argon atmosphere. In a further particular embodiment, the step al) is performed at a temperature between 15 °C and 40 °C, preferably about 20 °C. In a further particular embodiment, the step al) is performed from 10 to 24 hours, preferably from 12 to 18 hours, more preferably about 16 hours. In a further particular embodiment, the step al) is performed under blue LED irradiation ranging from 350 to 450 nm, preferably about 405 nm. Another object of the invention is a molecule obtained by a process as above defined. A further object of the invention is a molecule selected in a group consisting of:

[0443] - N-(2-(pentafluoro-X6-sulfaneyl)-l-(p-tolyl)ethyl)-l, 1-diphenylmethanimine (4a);

[0444] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 -(m-tolyl)ethyl)- 1 , 1 -diphenylmethanimine (4b);

[0445] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 -(o-tolyl)ethyl)- 1 , 1 -diphenylmethanimine (4c);

[0446] - N-(l-(4-(tert-butyl)phenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)-l, 1-diphenylmethanimine (4d);

[0447] - 4-( l -((di phenyl methyl ene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Phenyl acetate (4e);

[0448] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 -phenylethyl)- 1 , 1 -diphenylmethanimine (4f);

[0449] - N-( 1 -(naphthal en-2-yl )-2-(pentafl uoro-X6-sulfaneyl jethyl )- 1 , 1 -diphenylmethanimine (4g);

[0450] - N-( 1 -(4-chlorophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4h);

[0451] - N-(l-(4-bromophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)-l, 1-diphenylmethanimine (4i);

[0452] - N-(l-(4-iodophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1,1 -diphenylmethanimine (4j);

[0453] - N-( 1 -([ 1 , 1l-biphenyl]-4-yl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4k);

[0454] - 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Benzonitrile (41);

[0455] - N-( 1 -(4-nitrophenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4m);

[0456] - 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X.6-sulfaneyl)ethyl)Benzaldehyde (4n);

[0457] - N-(2-(pentafluoro-X6-sulfaneyl)- 1 , 1 -diphenylethyl)- 1 , 1 -diphenylmethanimine (4o);

[0458] - N-( 1 -(pentafluoro-X6-sulfaneyl)-2-phenylpropan-2-yl)- 1 , 1 -diphenylmethanimine (4p);

[0459] - N-(2-(pentafluoro-X6-sulfaneyl)-l-(thiophen-2-yl)ethyl)-l, 1-diphenylmethanimine (4q);

[0460] (1 S,2R,5S)-2-isopropyl-5-methylcyclohexyl 4-(l-((diphenylmethylene)amino)-2- (pentafluoro-k6-sulfaneyl)ethyl)benzoate (4r);

[0461] ((S)-4-(prop- 1 -en-2-yl)cyclohex- 1 -en- 1 -yl)Methyl 4-( 1 -((diphenylmethylene)amino)-2-

[0462] (pentafluoro-k6-sulfaneyl)ethyl)benzoate (4s);

[0463] ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6- sulfaneyl)ethyl)benzoate (4t);

[0464] 2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(l-

[0465] ((diphenylmethylene)amino)-2-(pentafluoro-A6-sulfaneyl)ethyl)benzoate (4u);

[0466] (S)-3,7-dimethyloct-6-en-l-yl 4-(l -((diphenylmethylene)amino)-2-(pentafluoro-A6- sulfaneyl)ethyl)Benzoate (4v);

[0467] 4-Formyl-2-methoxyphenyl 4-(l -((di phenyl methylene)amino)-2-(pentafluoro-A6- sulfaneyl)ethyl)benzoate (4w);

[0468] (8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,ll,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(l -((diphenylmethylene)amino)-2-(pentafluoro-A6- sulfaneyl)ethyl)benzoate (4x); and

[0469] (R)-2, 5 ,7, 8-Tetramethy L2-((4R, 8R)-4, 8, 12-trimethyltridecyl)chroman-6-yl 4-( 1 -

[0470] ((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (4y). comprising a pentafluorosulfanyl (SF5) group, preferably obtained

[0471] A second process is based on the reactivity of molecules (I) under single-electron transfer conditions.

[0472] Thus provided herein a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a2) reacting a compound of formula (I) as defined herein with a molecule comprising a styrene unit in presence of diethyl 2,6-dimethyl-l,4-dihydropyridine-3,5-dicarboxylate, [Ir(dF(CF3)ppy)2dtbbpy]PFe, and chlorohydric acid, under blue LED irradiation; and b2) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0473] In a particular embodiment, the step a2) is performed under argon atmosphere. In a further particular embodiment, the step a2) is performed at a temperature between 15 °C and 40 °C, preferably about 20 °C. In a further particular embodiment, the step a2) is performed from 10 to 24 hours, preferably from 12 to 18 hours, more preferably about 16 hours. In a further particular embodiment, the step a2) is performed under blue LED irradiation ranging from 400 to 500 nm, preferably about 405 or 455 nm.

[0474] Another object of the invention is a molecule obtained by a process as above defined.

[0475] A further object of the invention is a molecule selected in a group consisting of:

[0476] - (4-(tert-butyl)phenethyl)Pentafluoro-X6-sulfane (5b);

[0477] - (4-(chloromethyl)phenethyl)Pentafluoro-X6-sulfane (5e);

[0478] - Pentafluoro(4-iodophenethyl)- X6-sulfane (5h);

[0479] - (2-([l,l'-biphenyl]-4-yl)ethyl)Pentafluoro-X6-sulfane (5j);

[0480] - (1 S,2R,5S)-2-Isopropyl-5-methylcyclohexyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5k);

[0481] (S)-(4-(prop- 1 -en-2-yl)cyclohex- 1 -en- 1 -yl)Methyl 4-(2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (51);

[0482] ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5m); 2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(2-(pentafhioro-X6- sulfaneyl)ethyl)benzoate (5n);

[0483] - (S)-3,7-Dimethyloct-6-en-l-yl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5o);

[0484] - 4-Formyl-2-methoxyphenyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5p); and

[0485] (8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,l l,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5q).

[0486] For preparing SFs-substituted molecules, the inventors further proposed two other alternatives of processes starting from a molecule comprising an azabicyclobutanyl or a bicyclobutanyl.

[0487] Thus provided herein a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a3) reacting a compound of formula (I) as defined herein with a molecule comprising an azabicyclobutanyl in presence of thioxanthone (TXO) and ethyl acetate under blue LED irradiation; and b3) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0488] In a particular embodiment, the step a3) is performed under argon atmosphere. In a further particular embodiment, the step a3) is performed at a temperature between 15 °C and 40 °C, preferably about 20 °C. In a further particular embodiment, the step a3) is performed from 10 to 24 hours, preferably from 10 to 16 hours, more preferably about 12 hours. In a further particular embodiment, the step a3) is performed under blue LED irradiation ranging from 400 to 500 nm, preferably about 405 nm.

[0489] In a further particular embodiment, the azabicyclobutanyl has the following formula (A): in which R? is a radical selected in a group consisting of a phenyl, a phenyl substituted by a (Ci-Ce)alkyl optionally substituted by at least one halogen, and a CO-phenyl; and Rs is a radical selected in a group consisting of a hydrogen, and a (Ci-Ce)alkyl. A particular object of the invention is a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a3) reacting a compound of formula (I) as defined herein with a molecule comprising an azabicyclobutanyl having the following formula (A): in which R7 is a radical selected in a group consisting of a phenyl, a phenyl substituted by a (Ci-Ce)alkyl optionally substituted by at least one halogen, and a CO-phenyl; and Rs is a radical selected in a group consisting of a hydrogen, and a (Ci-Ce)alkyl; in presence of thioxanthone (TXO) and ethyl acetate under blue LED irradiation; and b3) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0490] Another object of the invention is a molecule obtained by a process as above defined.

[0491] A further object of the invention is a molecule selected in a group consisting of:

[0492] - N-( l-(pentafluoro-k6-sulfaneyl)-3-phenylazeti din-3 -yl)- 1, 1-diphenylmethanimine (3a);

[0493] - l,l-bis(4-fluorophenyl)-N-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3b);

[0494] - l,l-bis(4-bromophenyl)-N-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3 c)

[0495] - l,l-bis(4-chlorophenyl)-N-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3d);

[0496] - N-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazeti din-3 -yl)-l,l-di-p-tolylmethanimine (3e); l,l-bis(4-methoxyphenyl)-N-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3- yl)methanimine (3f);

[0497] - A-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-9Z7-fluoren-9-imine (3g);

[0498] 1 -(naphthal en-2-yl)-N-(l -(pentafl uoro-k6-sulfaneyl )-3 -phenylazeti din-3 -yl)- 1 - phenylmethanimine (3h); l-(4-nitrophenyl)-N-(l-(pentafluoro-k6-sulfaneyl)-3 -phenylazeti din-3 -yl)-l- phenylmethanimine (3i); l-(3,4-dimethylphenyl)-N-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3j); 1 -(2-methoxyphenyl)-N-(l -(pentafl uoro-X6-sulf aneyl )-3 -phenylazeti din-3 -yl)- 1 - phenylmethanimine (3 k);

[0499] N-(l -(pentafl uoro-k6-sulfaneyl )-3 -phenylazeti din-3 -yl)- 1 -phenyl- 1 -(pyri din-3 - yl)methanimine (31); l-(4-bromophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3 m);

[0500] 2-(4-((4-chlorophenyl)((l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3- yl)imino)methyl)phenoxy)-2-methylpropanoate (3n);

[0501] - N-( 1 -(pentafl uoro-k6-sul faneyl )-3 -(p-tolyl)azetidin-3 -yl)- 1 , 1 -diphenylmethanimine (3 a 1 );

[0502] N-( 1 -(pentafl uoro-k6-sul fan eyl )-3 -(4-(trifluoromethyl)phenyl)azeti din-3 -yl)- 1,1- diphenylmethanimine (3a2);

[0503] (3-((diphenylmethylene)amino)-l-(pentafluoro-X.6-sulfaneyl)azetidin-3- yl)(phenyl)methanone (3a3); and

[0504] N-2-methyl- l-(pentafluoro-X.6-sulfaneyl)-3 -phenylazeti din-3 -yl)- 1,1 -diphenylmethanimine (3a4).

[0505] Thus also provided herein a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a4) reacting a compound of formula (I) as defined herein with a molecule comprising a bicyclobutanyl in presence of thioxanthone (TXO) and ethyl acetate under blue LED irradiation; and b4) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0506] In a particular embodiment, the step a4) is performed under argon atmosphere. In a further particular embodiment, the step a4) is performed at a temperature between 15 °C and 40 °C, preferably about 20 °C. In a further particular embodiment, the step a4) is performed from 10 to 24 hours, preferably from 10 to 16 hours, more preferably about 12 hours. In a further particular embodiment, the step a3) is performed under blue LED irradiation ranging from 400 to 500 nm, preferably about 405 nm.

[0507] In a further particular embodiment, the bicyclobutanyl has the following formula (B): in which R9 is a radical selected in a group consisting of a phenyl and a phenyl substituted by a halogen or a (Ci-Ce)alkyl optionally substituted by at least one halogen.

[0508] A particular object of the invention is a process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a4) reacting a compound of formula (I) as defined herein with a molecule comprising a bicyclobutanyl having the following formula (B): in which R9 is a radical selected in a group consisting of a phenyl and a phenyl substituted by a halogen or a (Ci-Ce)alkyl optionally substituted by at least one halogen; in presence of thioxanthone (TXO) and ethyl acetate under blue LED irradiation; and b4) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

[0509] Another object of the invention is a molecule obtained by a process as above defined.

[0510] A further object of the invention is a molecule selected in a group consisting of:

[0511] - Methyl 3 -((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3 -phenylcyclobutane- 1- carboxylate (6a);

[0512] - Methyl 3-((bis(4-fluorophenyl)methylene)amino)- l-(pentafluoro-A6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6b);

[0513] Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6c anti);

[0514] Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6c syn);

[0515] Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6d anti)

[0516] Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6d syn);

[0517] - Methyl-3-((di-p-tolylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-phenylcyclobutane- 1 -carboxylate (6e);

[0518] Methyl-3-((bis(4-methoxyphenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6f) ; - Methyl 3 -((9 / / - fl uoren-9-ylidene)amino)- l -(pentafl uoro-k6-sulfaneyl)-3 -phenylcyclobutane- 1 -carboxylate (6g);

[0519] - Methyl (Z)-3-(((2-methoxyphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)- 3 -phenyl cy cl obutane- 1 -carb oxy 1 ate (6h) ;

[0520] - Methyl 3-(((3,4-dimethylphenyl)(phenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcy cl obutane- 1 -carboxylate (6i);

[0521] Methyl 3 -(((4-bromophenyl)(phenyl)methylene)amino)- 1 -(pentad uoro-X6-sul faney 1 )-3 - phenylcyclobutane- 1 -carboxylate (6j );

[0522] Methyl-3-(((2-methoxyphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6k);

[0523] Methyl 3-(((4-nitrophenyl)(phenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (61);

[0524] Methyl l-(pentafluoro-k6-sulfaneyl)-3-phenyl-3-((phenyl(pyridin-3- yl)methylene)amino)cy cl obutane- 1 -carboxylate (6m);

[0525] Methyl-3-((diphenylmethylene)amino)-3 -(3 -fluorophenyl)- l^pentafluoro-X6- sulfaneyl)cy cl obutane- 1 -carboxylate (6al );

[0526] Methyl-3-(4-chlorophenyl)-3-((diphenylmethylene)amino)-l-(pentafluoro-k6- sulfaneyl)cy cl obutane- 1 -carboxylate (6a2);

[0527] Methyl-3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-(4- (trifluoromethyl)phenyl)cyclobutane-l -carboxylate (6a3); and

[0528] Methyl-3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-(3- (trifluoromethyl)phenyl)cyclobutane-l -carboxylate (6a4).

[0529] The processes or methods for preparing the compounds of formula (I), (II), or (III), pentafluorosulfanyldichloramine, and molecules comprising a pentafluorosulfanyl (SFs) group described above all include a final step for recovering these compounds or molecules. It is understood that the person skilled in the art knows how to recover these compounds or after a reaction step thanks to his general knowledge as an organic chemist. These recovery steps may include one or more reaction mixture treatment steps and one or more isolation and / or purification steps. For example, isolation and purification steps include distillation, evaporation, concentration, filtration and / or drying steps.

[0530] Further aspects and advantages of the invention will be disclosed in the following experimental section, which should be regarded as illustrative and not limiting. EXAMPLES

[0531] 1. Preparation of the compounds of formula (I) according to the invention

[0532] The compound of formula (I) according to the invention were prepared by the general procedure GP4 (steps 1 to 3) in which pentafluorosulfanyldichloramine (SF5NCI2) was generated by the two following steps 1 and 2, and, then was reacted to the diazo compound of formula (I’) in a step 3) thereby allowing to provide the compounds of formula (I).

[0533] Step 1 :

[0534] An oven-dried 100 mL pressure-resistant bottle was added with 2, 3, 4,5,6- pentafluorobenzamide (3.75 mmol, 791.2 mg, 1.0 equiv.), Ss (0.47 mmol, 120.0 mg, 0.125 equiv.), trichloroisocyanuric acid (2.62 mmol, 606.0 mg, 0.7 equiv.) and tetrabutylammonium bromide (0.375 mmol, 122 mg, 10 mol%). The vessel was brought under argon atmosphere using glovebox. Then 25.0 mL anhydrous Acetonitrile were injected in pressure-resistant bottle. Pressure-resistant bottle was wrapped in aluminum foil. The reaction was stirred for 4 h at 40 °C.

[0535] Step 2:

[0536] An oven-dried 100 mL two-chamber reactor was added AgF2 powder (18.75 mmol, 2.72 g, 5 equiv. refer to 2,3,4,5,6-pentafluorobenzamide) in chamber 1 (Cl). Next, chamber 2 (C2) was charged with trichloroisocyanuric acid (15 mmol, 3.48 mg, 4.0 equiv.) and potassium fluoride (33.75 mmol, 1.95 g, 9.0 equiv.). The reactor was brought into glovebox and sealed. Then the 25.0 mL anhydrous Acetonitrile was added in chamber 2. And the reaction mixture in pressureresistant bottle was taken out with a syringe and filtered into chamber 1 through a 0.22 pm PTFE syringe filter. Then, the two-chamber reactor was wrapped in aluminum foil. The reaction of Step 2 was stirred for 24 h at -15 °C.

[0537] Step 3:

[0538] An oven-dried 150 mL round bottom flask was added diazo compound (1.25 mmol, 1 equiv.). The flask was brought into glovebox and 10.0 mL anhydrous DCM was added. Then the mixture in two-chamber reactor was also brought in to glovebox. The mixture was taken out with a syringe and filtered into a oven-dried 100 mL pressure-resistant bottle through a 0.22 pm PTFE syringe filter. The filtrate was then extracted by / / -Hexane (6 * 5 mL) and the / / - Hexane was added to DCM solution. The mixture was taken out of glovebox and reacted under 40 °C for 2 h. After completed, the reaction was quenched by water (20 mL) and extracted by ethyl acetate (3 * 15 mL), the combined organic layers were washed by saturated brine (3 * 15 mL) and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material obtained was then purified by column chromatography on silica gel.

[0539] N-(pentafluoro-k6-sulfaneyl)-l,l-diphenylmethanimine (2a)

[0540] The compound 2a was obtained as a colorless oil in 82% yield using (diazomethylene)dibenzene following the GP4 after column chromatography on silica gel with pentane.

[0541] 'H NMR (300 MHz, Chloroform-; / ) 5 7.67 - 7.59 (m, 1H), 7.56 - 7.42 (m, 2H), 7.41 - 7.34 (m, 1H), 7.29 - 7.22 (m, 1H).

[0542] 19F NMR (282 MHz, Chloroform-; / ) 5 82.8 - 80.3 (m, IF), 69.4 - 68.7 (m, 4F).

[0543] 13C NMR (75 MHZ, Chloroform-; / ) 5 174.9 (p, J = 6.0 Hz), 137.5, 137.1 (p, = 2.5 Hz), 133.2, 130.6, 129.1, 128.5, 127.8, 127.0 - 126.7 (m).

[0544] HRMS (ESI) calculated for C13H11F5NS: 308.0527 [M+H]+, Found: 308.0526. l,l-Bis(4-fluorophenyl)-N-(pentafluoro-k6-sulfaneyl)methanimine (2b)

[0545] The compound 2b was obtained as a colorless oil in 79% yield using 4,4'- (diazomethylene)bis(fluorobenzene) following the GP4 after column chromatography on silica gel with pentane.

[0546] XH NMR (300 MHz, Chloroform-; / ) 5 7.67 - 7.58 (m, 2H), 7.26 - 7.21 (m, 2H), 7.20 - 7.12 (m, 2H), 7.11 - 7.01 (m, 2H).

[0547] 19F NMR (282 MHz, Chloroform-; / ) 5 82.5 - 80.1 (m, IF), 69.3 - 68.6 (m, 4F), -104.5 - -104.8 (m, IF), -110.5 - -110.7 (m, IF).

[0548] 13C NMR (75 MHz, Chloroform-; / ) 5 173.0 - 172.5 (m), 166.2 (d, J= 229.0 Hz), 162.8 (d, J= 222.6 Hz), 133.2 - 132.9 (m), 129.2 - 128.6 (m), 115.8 (d, J= 22.0 Hz), 115.3 (d, J= 22.0 Hz). HRMS (ESI) calculated for C13H9F7NS: 344.0338 [M+H]+, Found: 344.0340. l,l-Bis(4-bromophenyl)-N-(pentafluoro-k6-sulfaneyl)methanimine (2c)

[0549] The compound 2c was obtained as a colorless oil in 72% yield using 4,4'- (diazomethylene)bis(bromobenzene) following the GP4 after column chromatography on silica gel with pentane.

[0550] ‘H NMR (300 MHz, Chloroform-; / ) 5 7.65 - 7.57 (m, 2H), 7.55 - 7.42 (m, 4H), 7.15 - 7.08 (m, 2H).

[0551] 19F NMR (282 MHz, Chloroform-; / ) 5 82.1 - 79.1 (m, IF), 69.4 - 68.3 (m, 4F).

[0552] 13C NMR (75 MHz, Chloroform-; / ) 5 172.9 - 172.5 (m), 135.7, 135.5 (p, J= 2.7 Hz), 132.0, 131.9, 131.3, 128.9, 128.6 - 128.2 (m), 123.9.

[0553] HRMS (ESI) calculated for CisHzBrcFsNS: 463.8737 [M+H]+, Found: 463.8735. l,l-Bis(4-chlorophenyl)-N-(pentafluoro-k6-siilfaneyl)methanimine (2d)

[0554] The compound 2d was obtained as a colorless oil in 78% yield using 4,4'- (diazomethylene)bis(chlorobenzene) following the GP4 after column chromatography on silica gel with pentane.

[0555] XH NMR (300 MHz, Chloroform-; / ) 5 7.58 - 7.51 (m, 2H), 7.48 - 7.42 (m, 2H), 7.40 - 7.32 (m, 2H), 7.22 - 7.14 (m, 2H).

[0556] 19F NMR (282 MHz, Chloroform-; / ) 5 82.0 - 79.6 (m, IF), 69.5 - 68.3 (m, 4F).

[0557] 13C NMR (75 MHz, Chloroform-; / ) 5 172.8 - 172.4 (m), 140.2, 135.7, 135.3, 135.2 - 135.0 (m), 131.8, 129.0, 128.4, 128.3 - 128.0 (m).

[0558] HRMS (ESI) calculated for C13H9CI2F5NS: 375.9747 [M+H]+, Found: 375.9750.

[0559] N-(pentafluoro-k6-suifaneyl)-l,l-di-p-tolylmethanimine (2e)

[0560] The compound 2e was obtained as a white solid in 72% yield using 4,4'- (diazomethylene)bis(methylbenzene) following the GP4 after column chromatography on silica gel with pentane.

[0561] ‘H NMR (300 MHz, Chloroform-; / ) 5 7.62 - 7.54 (m, 2H), 7.20 - 7.12 (m, 2H), 6.98 - 6.91 (m, 2H), 6.88 - 6.81 (m, 2H), 3.87 (s, 3H), 3.84 (s, 3H).

[0562] 19F NMR (282 MHz, Chloroform-; / ) 5 84.9 - 82.5 (m, IF), 70.3 - 69.4 (m, 4F).

[0563] 13C NMR (75 MHz, Chloroform-; / ) 5 175.2 (p, J= 6.1 Hz), 144.1, 139.1, 135.1 - 134.5 (m), 130.7, 129.2, 128.3, 127.1 - 126.6 (m), 21.6, 21.4.

[0564] HRMS (ESI) calculated for C15H15F5NS: 336.0840 [M+H]+, Found: 336.0839. l,l-Bis(4-methoxyphenyl)-N-(pentafluoro-k6-suifaneyl)methanimine (2f)

[0565] The compound 2f was obtained as a colorless oil in 68% yield using 4,4'- (diazomethylene)bis(methoxybenzene) following the GP4 after column chromatography on silica gel with pentane.

[0566] 'H NMR (300 MHz, Chloroform-; / ) 5 7.54 - 7.47 (m, 2H), 7.26 - 7.21 (m, 2H), 7.18 - 7.09 (m, 4H), 2.43 (s, 3H), 2.39 (s, 3H).

[0567] 19F NMR (282 MHz, Chloroform-; / ) 5 83.8 - 81.4 (m, IF), 69.9 - 68.8 (m, 4F).

[0568] 13C NMR (75 MHz, Chloroform-; / ) 5 174.6 - 174.1 (m), 163.8, 160.0, 132.9, 130.2 - 129.9 (m), 129.7, 128.9 - 127.7 (m), 113.8, 113.1, 55.5, 55.3.

[0569] HRMS (ESI) calculated for C15H15F5NO2S: 368.0738 [M+H]+, Found: 368.0748.

[0570] N-(pentafluoro-k6-siilfaneyl)-9H-fluoren-9-imine (2g)

[0571] The compound 2g was obtained as a yellowish solid in 70% yield using 9-diazo-9Z / -fluorene following the GP4 after column chromatography on silica gel with pentane. 'H NMR (300 MHz, Chloroform-; / ) 5 8.17 - 8.06 (m, 1H), 7.81 - 7.72 (m, 1H), 7.56 - 7.40 (m, 4H), 7.31 - 7.26 (m, 1H), 7.26 - 7.21 (m, 1H).

[0572] 19F NMR (282 MHz, Chloroform-; / ) 5 82.4 - 80.0 (m, IF), 65.6 - 64.7 (m, 4F).

[0573] 13C NMR (75 MHz, Chloroform-; / ) 5 168.7 - 168.3 (m), 146.1, 141.6, 137.6 - 137.3 (m), 134.9, 134.2, 130.2 (p, J= 7.8 Hz), 129.9, 129.0, 129.0, 125.2, 120.4, 119.8.

[0574] HRMS (ESI) calculated for C13H9F5NS: 306.0370 [M+H]+, Found: 306.0380.

[0575] (Z)-l-(naphthalen-2-yl)-N-(pentafluoro-k6-sulfaneyl)-l-phenylmethanimine (2h)

[0576] The compound 2h was obtained as a white solid in 80% yield using 2- (diazo(phenyl)methyl)naphthalene following the GP4 after column chromatography on silica gel with pentane.

[0577] 'H NMR (300 MHz, Chloroform-; / ) 5 8.08 - 7.98 (m, 1H), 7.98 - 7.81 (m, 4H), 7.80 - 7.70 (m, 2H), 7.70 - 7.56 (m, 3H), 7.62 - 7.43 (m, 6H), 7.42 - 7.28 (m, 3H).

[0578] 19F NMR (282 MHz, Chloroform-; / ) 5 83.1 - 80.4 (m, IF), 69.6 - 68.7 (m, 4F).

[0579] 13C NMR (75 MHz, Chloroform-; / ) 5 174.8 (dt, J= 16.7, 5.9 Hz), 137.5, 137.3 - 137.0 (m),

[0580] 135.5, 134.8, 134.8 - 134.5 (m), 134.1, 133.2, 133.1, 132.4, 132.0, 130.7, 129.6, 129.2, 128.8,

[0581] 128.5, 128.4, 128.4, 127.9, 127.8, 127.7, 127.6, 127.3, 127.2 - 126.9 (m), 126.8, 126.5 - 126.2 (m), 125.0, 124.3 - 124.0 (m).

[0582] HRMS (ESI) calculated for C17H13F5NS: 358.0683 [M+H]+, Found: 358.0687.

[0583] (E)-l-(4-nitrophenyl)-N-(pentafluoro-k6-siilfaneyl)-l-phenylmethanimine (2i)

[0584] The compound 2i was obtained as a colorless oil in 77% yield using l-(diazo(phenyl)methyl)- 4-nitrobenzene following the GP4 after column chromatography on silica gel with pentane / ethyl acetate (50 / 1).

[0585] 'H NMR (300 MHz, Chloroform-; / ) 5 8.38 - 8.30 (m, 2H), 8.23 - 8.17 (m, 1H), 7.84 - 7.75 (m, 1H), 7.62 - 7.55 (m, 3H), 7.54 - 7.46 (m, 3H), 7.44 - 7.37 (m, 2H), 7.28 - 7.22 (m, 1H).

[0586] 19F NMR (282 MHz, Chloroform-; / ) 5 81.7 - 78.0 (m, IF), 69.6 - 67.8 (m, 4F).13C NMR (75 MHz, Chloroform-; / ) 5 172.4 - 172.0 (m), 150.3, 148.2, 143.9, 142.6, 136.4, 135.9 - 135.5 (m), 133.9, 133.5, 131.4, 130.7, 130.4, 130.1, 129.8, 128.9, 128.9, 128.7, 128.7, 128.3, 128.2 - 128.1 (m), 127.7, 126.7 - 126.2 (m), 123.8, 123.5, 123.5, 123.2.

[0587] HRMS (ESI) calculated for C13H10F5N2O2S: 353.0378 [M+H]+, Found: 353.0375.

[0588] (E)-l-(3,4-dimethylphenyl)-N-(pentafluoro-k6-sulfaneyl)-l-phenylmethanimine (2j)

[0589] The compound 2j was obtained as a white solid in 89% yield using 4-(diazo(phenyl)methyl)- 1,2-dimethylbenzene following the GP4 after column chromatography on silica gel with pentane.

[0590] 'H NMR (300 MHz, Chloroform-; / ) 5 7.66 - 7.43 (m, 3H), 7.43 - 7.33 (m, 1H), 7.25 - 6.96 (m, 3H), 2.35 - 2.23 (m, 6H).

[0591] 19F NMR (282 MHz, Chloroform-; / ) 5 83.7 - 80.9 (m, IF), 69.9 - 68.5 (m, 4F).

[0592] 13C NMR (75 MHz, Chloroform-; / ) 5 175.1 - 174.8 (m), 143.0, 137.8, 137.8, 137.7 - 137.4 (m), 137.0, 136.1, 135.0, 134.8 - 134.6 (m), 133.0, 131.1, 130.6, 129.7, 128.9, 128.9, 128.8, 128.4, 127.9 - 127.7 (m), 127.6, 126.9 - 126.8 (m), 124.5 - 124.3 (m), 20.0, 19.8, 19.7.

[0593] HRMS (ESI) calculated for C15H15F5NS: 336.0840 [M+H]+, Found: 336.0839.

[0594] (E)-l-(2-methoxyphenyl)-N-(pentafluoro-k6-sulfaneyl)-l-phenylmethanimine (2k)

[0595] The compound 2k was obtained as a colorless oil in 81% yield using l-(diazo(phenyl)methyl)- 2 -methoxybenzene following the GP4 after column chromatography on silica gel with pentane.XH NMR (300 MHz, Chloroform-; / ) 5 7.68 - 7.60 (m, 2H), 7.53 - 7.41 (m, 2H), 7.38 - 7.32 (m, 2H), 7.17 - 7.10 (m, 1H), 7.08 - 7.00 (m, 1H), 6.98 - 6.92 (m, 1H), 3.70 (s, 3H).

[0596] 19F NMR (282 MHz, Chloroform-; / ) 5 82.8 - 80.5 (m, IF), 67.4 - 66.2 (m, 4F).

[0597] 13C NMR (75 MHz, Chloroform-; / ) 5 173.5 - 173.2 (m), 155.7, 137.2 - 136.1 (m), 132.9, 130.7, 129.8, 128.5, 128.1 - 127.9 (m), 126.7, 119.9, 110.9, 55.7.

[0598] HRMS (ESI) calculated for C14H13F5NOS: 338.0633 [M+H]+, Found: 338.0638. (Z)-N-(pentafluoro-k -sulfaneyl)-l-phenyl-l-(pyridin-3-yl)methanimine (21)

[0599] The compound 21 was obtained as a yellowish solid in 62% yield using 3- (diazo(phenyl)methyl)pyridine following the GP4 after column chromatography on silica gel with pentane / ethyl acetate(40 / l).

[0600] 'H NMR (300 MHz, Chloroform-; / ) 5 8.64 - 8.34 (m, 2H), 7.92 - 7.30 (m, 4H), 7.30 - 7.20 (m, 2H), 7.18 - 7.08 (m, 1H).

[0601] 19F NMR (282 MHz, Chloroform-; / ) 5 82.2 - 78.8 (m, IF), 69.4 - 68.3 (m, 4F).

[0602] 13C NMR (75 MHz, Chloroform-6 5 174.3 - 172.1 (m), 153.4, 151.8, 150.4, 147.9 - 145.4 (m), 137.1, 136.5 (dt, J = 4.4, 1.9 Hz), 136.3, 135.3, 134.7 - 134.1 (m), 133.7, 133.2 - 132.9 (m), 130.5, 129.6, 128.8, 128.8, 128.5, 128.2, 127.7, 126.7 - 126.4 (m), 123.3, 122.6.

[0603] HRMS (ESI) calculated for C12H10F5N2S: 309.0479 [M+H]+, Found: 309.0479.

[0604] (E)-l-(4-bromophenyl)-N-(pentafluoro-k6-sulfaneyl)-l-phenylmethanimine (2m)

[0605] The compound 2m was obtained as a colorless oil in 75% yield using l-bromo-4- (diazo(phenyl)methyl)benzene following the GP4 after column chromatography on silica gel with pentane.

[0606] XH NMR (300 MHz, Chloroform-; / ) 5 7.64 - 7.56 (m, 2H), 7.55 - 7.48 (m, 2H), 7.48 - 7.35 (m, 3H), 7.25 - 7.21 (m, 1H), 7.17 - 7.09 (m, 1H).

[0607] 19F NMR (282 MHz, Chloroform-; / ) 5 82.4 - 79.8 (m, IF), 69.3 - 68.6 (m, 4F).

[0608] 13C NMR (75 MHz, Chloroform-; / ) 5 174.1 - 173.3 (m), 136.9, 136.7 - 136.5 (m), 136.4, 136.3, 136.1 - 135.9 (m), 133.4, 132.0, 131.8, 131.1, 130.6, 129.4, 128.6, 128.6, 128.5 - 128.4 (m), 127.9, 126.8 - 126.6 (m), 123.6.

[0609] HRMS (ESI) calculated for Ci3HioBrF5NS: 385.9632 [M+H]+, Found: 385.9634.

[0610] Isopropyl (E)-2-(4-((4-chlorophenyl)((pentafluoro-k6-sulfaneyl)imino)methyl)phenoxy)- 2-methylpropanoate (2n)

[0611] The compound 2n was obtained as a colorless oil in 50% yield using isopropyl 2-(4-((4- chlorophenyl)(diazo)methyl)phenoxy)-2-methylpropanoate following the GP4 after column chromatography on silica gel with pentane / ethyl acetate (100 / 2).

[0612] 'H NMR (300 MHz, Chloroform-; / ) 5 7.57 - 7.46 (m, 2H), 7.45 - 7.30 (m, 2H), 7.21 - 7.06 (m, 2H), 6.91 - 6.70 (m, 2H), 5.14 - 4.99 (m, 1H), 1.67 - 1.59 (m, 6H), 1.21 - 1.16 (m, 6H).

[0613] 19F NMR (282 MHz, Chloroform-; / ) 5 83.9 - 80.2 (m, IF), 70.3 - 68.6 (m, 4F).

[0614] 13C NMR (75 MHz, Chloroform-; / ) 5 173.4 - 173.2 (m), 172.8, 160.4, 156.7, 139.7, 136.0, 135.3, 132.3, 131.9, 129.5 - 129.2 (m), 128.7, 128.4 - 128.3 (m), 128.1, 117.4, 117.3, 79.5, 79.4, 69.4, 69.2, 25.5, 25.3, 21.5, 21.5.

[0615] HRMS (ESI) calculated for C20H22CIF5NO3S: 486.0924 [M+H]+, Found: 486.0940.

[0616] (lR,3S,5r,7r)-Adamantan-2-yl 2-(3-((Z)-((pentafluoro-k6- sulfaneyl)imino)(phenyl)methyl)phenyl)propanoate (2o)

[0617] The compound 2o was obtained as colorless oil in 84% yield using (lR,3S,5r,7r)-adamantan- 2-yl 2-(3-(diazo(phenyl)methyl)phenyl)propanoate following the GP4 after column chromatography on silica gel with pentane / ethyl acetate( 100 / 4).

[0618] 'H NMR (300 MHz, Chloroform-; / ) 5 7.69 - 7.44 (m, 3H), 7.43 - 7.36 (m, 2H), 7.35 - 7.27 (m, 2H), 7.25 - 7.09 (m, 2H), 4.93 - 4.82 (m, 1H), 3.76 (p, J= 7.1 Hz, 1H), 1.95 - 1.59 (m, 12H), 1.55 - 1.34 (m, 5H).

[0619] 19F NMR (282 MHz, Chloroform-; / ) 5 82.7 - 80.3 (m, IF), 69.4 - 68.7 (m, 4F).

[0620] 13C NMR (75 MHz, Chloroform-; / ) 5 174.9 - 174.4 (m), 173.2, 173.1, 141.5, 140.8, 140.1 - 139.8 (m), 137.7, 137.4, 137.5 - 137.1 (m), 137.2 - 136.8 (m), 133.2, 132.2, 130.6, 129.7, 129.5, 129.2, 128.6, 128.5, 128.3, 128.0, 127.7, 126.8 - 126.7 (m), 126.7 - 126.5 (m), 126.0, 125.6 - 125.4 (m), 46.0, 45.9, 37.3, 37.3, 36.3, 36.2, 36.2, 31.8, 31.7, 31.7, 31.6, 31.6, 31.5, 27.2, 27.1, 27.1, 26.9, 26.9, 18.1, 18.0.

[0621] HRMS (ESI) calculated for C26H29F5NO2S: 514.1834 [M+H]+, Found: 514.1833. Ethyl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-phenylacetate (2p)

[0622] The compound 2p was obtained as a colorless oil in 65% yield using ethyl 2-diazo-2- phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0623] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.87 - 7.77 (m, 2H), 7.70 - 7.63 (m, 1H), 7.55

[0624] - 7.49 (m, 2H), 4.48 (q, J= 7.1 Hz, 2H), 1.39 (t, J= 7.1 Hz, 3H).

[0625] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.8 - 76.4 (m), 65.7 - 64.7 (m).

[0626] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 165.1 - 164.7 (m), 163.8, 134.5, 131.0 - 130.8 (m), 129.4, 129.2, 63.4, 13.6.

[0627] HRMS (ESI) calculated for C10H11F5NO2S: 304.0425 [M+H]+, Found: 304.0427.

[0628] Ethyl (Z)-2-(4-bromophenyl)-2-((pentafluoro-k6-sulfaneyl)imino)acetate (2q)

[0629] The compound 2q was obtained as a colorless oil in 69% yield using ethyl 2-(4-bromophenyl)- 2-diazoacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0630] 'H NMR (300 MHz, Methylene Chloride-tfe) 5 7.76 - 7.62 (m, 4H), 4.48 (q, J= 7.1 Hz, 2H), 1.38 (t, J = 7.1 Hz, 3H).

[0631] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.3 - 75.9 (m), 65.7 - 64.7 (m).

[0632] 13C NMR (75 MHz, Methylene Chloride-tfe) 5 164.3 - 163.8 (m), 163.5, 132.6, 132.3, 131.3, 130.7, 129.9 - 129.8 (m), 129.8, 63.7, 13.6.

[0633] HRMS (ESI) calculated for CioHioBrFsNChS: 381.9530 [M+H]+, Found: 381.9531.

[0634] Ethyl (Z)-2-(4-nitrophenyl)-2-((pentafluoro-k6-sulfaneyl)imino)acetate (2r)

[0635] The compound 2r was obtained as a yellowish solid in 83% yield using ethyl 2-diazo-2-(4- nitrophenyl)acetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (3 / 2).

[0636] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 8.36 - 8.29 (m, 2H), 8.06 - 7.96 (m, 2H), 4.51 (q, J= 7.1 Hz, 2H), 1.40 (t, J= 7.1 Hz, 3H).

[0637] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 76.5 - 74.2 (m), 65.1 - 64.2 (m).

[0638] 13C NMR (75 MHz, Methylene Chloride-tfe) 5 163.1 - 162.8 (m), 131.1, 130.4, 124.1, 123.9, 64.1, 13.6.

[0639] HRMS (ESI) calculated for C10H10F5N2O4S: 349.0276 [M+H]+, Found: 349.0273.

[0640] Methyl (Z)-4-(2-methoxy-2-oxo-l-((pentafluoro-k6-sulfaneyl)imino)ethyl)benzoate (2s)

[0641] The compound 2s was obtained as a yellowish solid in 58% yield using methyl 4-(l-diazo-2- methoxy-2-oxoethyl)benzoate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (3 / 2).

[0642] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 8.16 - 8.10 (m, 2H), 7.91 - 7.84 (m, 2H), 4.02 (s, 3H), 3.93 (s, 3H).

[0643] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 77.5 - 75.2 (m), 65.1 - 64.3 (m).

[0644] 13C NMR (75 MHz, Methylene Chloride-tfe) 5 165.6, 163.9, 164.2 - 163.7 (m), 135.3, 134.4, 130.0, 129.3, 53.9, 52.5.

[0645] HRMS (ESI) calculated for C11H11F5NO4S: 348.0323 [M+H]+, Found: 348.0324.

[0646] Ethyl (Z)-2-(4-methoxyphenyl)-2-((pentafluoro-k6-sulfaneyl)imino)acetate (2t)

[0647] The compound 2t was obtained as a colorless oil in 85% yield using ethyl 2-diazo-2-(4- methoxyphenyl)acetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (3 / 2).

[0648] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.91 - 7.69 (m, 2H), 7.09 - 6.94 (m, 2H), 4.47 (q, J= 7.1 Hz, 2H), 3.89 (s, 3H), 1.38 (t, J = 7.1 Hz, 3H).

[0649] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 80.6 - 78.1 (m), 66.6 - 65.8 (m).

[0650] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 165.0, 164.2, 164.1 - 163.8 (m), 131.8, 123.1 - 122.8 (m), 114.7, 63.3, 55.7, 13.6.

[0651] HRMS (ESI) calculated for C11H13F5NO2S: 334.0531 [M+H]+, Found: 334.0531.

[0652] Ethyl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-(o-tolyl)acetate (2u)

[0653] The compound 2u was obtained as a colorless oil in 56% yield using ethyl 2-diazo-2-(o- tolyl)acetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0654] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.78 - 6.92 (m, 4H), 4.43 - 4.29 (m, 2H), 2.56

[0655] - 2.26 (m, 3H), 1.37 - 1.30 (m, 3H).

[0656] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.1 - 74.1 (m), 65.7 - 64.4 (m).

[0657] 13C NMR (75 MHz, Methylene Chloride-tfe) 5 166.9 - 166.4 (m), 163.8, 139.0, 134.3, 132.4, 132.2, 130.1, 129.9, 129.5, 126.2, 126.0 - 125.7 (m), 125.3, 63.8, 63.4, 20.9, 19.3, 13.7, 13.5. HRMS (ESI) calculated for C11H13F5NO2S: 318.0582 [M+H]+, Found: 318.0582.

[0658] Hexyl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-phenylacetate (2v)

[0659] The compound 2v was obtained as a colorless oil in 66% yield using hexyl 2-diazo-2- phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0660] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.88 - 7.75 (m, 2H), 7.70 - 7.62 (m, 1H), 7.55

[0661] - 7.46 (m, 2H), 4.41 (t, J = 6.7 Hz, 2H), 1.75 (p, J = 6.8 Hz, 2H), 1.41 - 1.29 (m, 6H), 0.92 - 0.86 (m, 3H).

[0662] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.8 - 76.5 (m), 65.7 - 64.9 (m).

[0663] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 165.1 - 164.6 (m), 164.0, 134.5, 131.2 - 130.7 (m), 129.4, 129.2, 67.5, 31.2, 28.1, 25.3, 22.4, 13.7.

[0664] HRMS (ESI) calculated for C26H29F5NO2S: 360.1051 [M+H]+, Found: 360.1052.

[0665] Isobutyl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-phenylacetate (2w)

[0666] The compound 2w was obtained as a colorless oil in 68% yield using isobutyl 2-diazo-2- phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0667] 'H NMR (300 MHz, Methylene Chloride-tfe) 5 7.9 - 7.8 (m, 2H), 7.7 - 7.6 (m, 1H), 7.6 - 7.5 (m, 2H), 4.2 (d, J= 6.6 Hz, 2H), 2.1 - 2.0 (m, 1H), 1.0 (s, 3H), 1.0 (s, 3H).

[0668] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.8 - 76.5 (m), 65.6 - 64.9 (m).

[0669] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 165.2 - 164.7 (m), 164.0, 134.5, 131.4 - 130.5 (m), 129.4, 129.2, 73.3, 27.5, 18.6.

[0670] HRMS (ESI) calculated for C12H15F5NO2S: 332.0738 [M+H]+, Found: 332.0739.

[0671] (S)-2-Methylbutyl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-phenylacetate (2x)

[0672] The compound 2x was obtained as a colorless oil in 72% yield using (S)-2-methylbutyl 2-diazo- 2-phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0673] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.93 - 7.75 (m, 2H), 7.70 - 7.62 (m, 1H), 7.55 - 7.48 (m, 2H), 4.32 - 4.26 (m, 1H), 4.24 - 4.17 (m, 1H), 1.89 - 1.77 (m, 1H), 1.52 - 1.40 (m, 1H), 1.28 - 1.19 (m, 1H), 0.98 - 0.90 (m, 6H).

[0674] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.8 - 76.5 (m), 65.7 - 64.8 (m).

[0675] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 165.2 - 164.7 (m), 164.0, 134.5, 131.2 - 130.7 (m), 129.4, 129.2, 71.9, 33.9, 25.7, 15.9, 10.8.

[0676] HRMS (ESI) calculated for C13H17F5NO2S: 346.0895 [M+H]+, Found: 346.0896.

[0677] 2-Methylbut-3-yn-2-yl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-phenylacetate (2y)

[0678] The compound 2y was obtained as a colorless oil in 60% yield using 2-methylbut-3-yn-2-yl 2- diazo-2-phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (100 / 15).

[0679] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 8.00 - 7.86 (m, 2H), 7.69 - 7.63 (m, 1H), 7.55

[0680] - 7.49 (m, 2H), 2.83 (s, 1H), 1.79 (s, 6H).

[0681] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.8 - 76.5 (m), 66.2 - 65.4 (m).

[0682] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 164.1 - 162.9 (m), 161.8, 134.4, 131.4 - 130.7 (m), 129.6, 129.2, 82.7, 76.3, 74.3, 28.3.

[0683] HRMS (ESI) calculated for C13H13F5NO2S: 342.0582 [M+H]+, Found: 342.0584.

[0684] Tetrahydrofuran-3-yl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-phenylacetate (2z)

[0685] The compound 2z was obtained as a colorless oil in 58% yield using tetrahydrofuran-3-yl 2- diazo-2-phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (1 / 4).

[0686] 'H NMR (300 MHz, Methylene Chloride-tfe) 5 7.9 - 7.8 (m, 2H), 7.7 - 7.6 (m, 1H), 7.6 - 7.5 (m, 2H), 5.7 - 5.6 (m, 1H), 4.0 - 3.9 (m, 2H), 3.9 - 3.8 (m, 2H), 2.4 - 2.2 (m, 1H), 2.2 - 2.1 (m, 1H).

[0687] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.8 - 76.5 (m), 65.8 - 65.1 (m).

[0688] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 165.0 - 163.7 (m), 163.5, 134.6, 131.0 - 130.2 (m), 129.3, 129.3, 78.3, 72.2, 66.8, 32.3.

[0689] HRMS (ESI) calculated for C12H13F5NO3S: 346.0531 [M+H]+, Found: 346.0531.

[0690] Cyclohexyl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-phenylacetate (2aa)

[0691] The compound 2aa was obtained as a white solid in 69% yield using cyclohexyl 2-diazo-2- phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (4 / 1).

[0692] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.93 - 7.77 (m, 2H), 7.69 - 7.60 (m, 1H), 7.56 - 7.46 (m, 2H), 5.21 - 5.11 (m, 1H), 2.02 - 1.93 (m, 2H), 1.80 - 1.71 (m, 2H), 1.60 - 1.51 (m, 3H), 1.46 - 1.26 (m, 3H).

[0693] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 79.1 - 76.7 (m), 65.9 - 65.2 (m).13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 165.4 - 164.5 (m), 163.3, 134.4, 131.5 - 130.3 (m), 129.4, 129.2, 76.6, 31.1, 25.1, 23.5.

[0694] HRMS (ESI) calculated for C14H17F5NO2S: 358.0895 [M+H]+, Found: 358.0894.

[0695] (2R,5S)-2-Isopropyl-5-methylcyclohexyl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2- phenylacetate (2ab)

[0696] The compound 2ab was obtained as a white solid in 68% yield using (2R,5S)-2-isopropyl-5- methylcyclohexyl 2-diazo-2-phenylacetate following the GP4 after column chromatography on silica gel with hexane / di chloromethane (10 / 1).

[0697] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.93 - 7.77 (m, 2H), 7.71 - 7.60 (m, 1H), 7.57 - 7.44 (m, 2H), 5.03 - 4.94 (m, 1H), 2.28 - 2.20 (m, 1H), 1.90 - 1.79 (m, 1H), 1.78 - 1.69 (m, 2H), 1.65 - 1.54 (m, 1H), 1.51 - 1.42 (m, 1H), 1.18 - 1.05 (m, 2H), 0.98 - 0.95 (m, 3H), 0.86 - 0.80 (m, 6H).

[0698] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.9 - 76.5 (m), 66.1 - 65.1 (m).

[0699] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 165.3 - 164.5 (m), 163.5, 134.3, 131.3 - 130.8 (m), 129.4, 129.1, 78.6, 46.7, 39.7, 33.9, 31.5, 25.5, 22.8, 21.7, 20.4, 15.2.

[0700] HRMS (ESI) calculated for C18H25F5NO2S: 414.1521 [M+H]+, Found: 414.1526.

[0701] 2-((lR,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl (Z)-2-((pentafluoro-k6- sulfaneyl)imino)-2-phenylacetate (2ac)

[0702] The compound 2ac was obtained as a colorless oil in 43% yield using 2-((lR,5S)-6,6- dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl 2-diazo-2-phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0703] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.88 - 7.77 (m, 2H), 7.70 - 7.61 (m, 1H), 7.54 - 7.47 (m, 2H), 5.37 - 5.32 (m, 1H), 4.50 - 4.35 (m, 2H), 2.45 - 2.34 (m, 3H), 2.29 - 2.19 (m, 2H), 2.12 - 2.03 (m, 2H), 1.27 (s, 3H), 0.80 (s, 3H).

[0704] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.9 - 76.4 (m), 65.8 - 64.8 (m).13C NMR (75 MHz, Methylene Chloride-tfe) 5 163.9, 143.1, 134.5, 131.1 - 130.6 (m), 129.4, 129.1, 119.5, 65.5, 45.6, 40.7, 37.9, 35.4, 31.5, 31.3, 25.9, 20.8.

[0705] HRMS (ESI) calculated for C19H23F5NO2S: 424.1364 [M+H]+, Found: 424.1363.

[0706] (lr,3r,5r,7r)-Adamantan-2-yl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-phenylacetate

[0707] (2ad)

[0708] The compound lad was obtained as a white solid in 69% yield using (lr,3r,5r,7r)-adamantan- 2-yl 2-diazo-2-phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0709] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.94 - 7.81 (m, 2H), 7.70 - 7.60 (m, 1H), 7.56 - 7.46 (m, 2H), 5.37 (t, J= 3.3 Hz, 1H), 2.13 (s, 2H), 1.99 - 1.85 (m, 7H), 1.83 - 1.76 (m, 3H), 1.64 - 1.57 (m, 2H).

[0710] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 79.1 - 76.8 (m, IF), 66.0 - 65.2 (m, 4F).

[0711] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 165.5 - 164.1 (m), 163.4, 134.4, 131.3 - 130.9 (m), 129.4, 129.2, 81.2, 37.1, 36.3, 32.0, 31.4, 27.1, 27.0.

[0712] HRMS (ESI) calculated for C18H21F5NO2S: 410.1208 [M+H]+, Found: 410.1213.

[0713] ((3aS,5S,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-2-phenylacetate (2ae)

[0714] The compound 2ae was obtained as a white solid in 59% yield using ((3aS,5S,5aR,8aR,8bS)- 2,2,7,7-tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl 2-diazo-2- phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (3 / 2).

[0715] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 8.02 - 7.85 (m, 2H), 7.70 - 7.61 (m, 1H), 7.57 - 7.45 (m, 2H), 5.56 (d, J= 5.0 Hz, 1H), 4.70 - 4.62 (m, 1H), 4.58 (d, J= 6.1 Hz, 2H), 4.40 - 4.35 (m, 1H), 4.28 - 4.23 (m, 1H), 4.21 - 4.13 (m, 1H), 1.46 (s, 4H), 1.44 (s, 4H), 1.34 (s, 5H), 1.34 (s, 5H).

[0716] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.9 - 76.5 (m), 65.9 - 65.0 (m).

[0717] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 164.6 - 164.2 (m), 163.8, 134.6, 130.9 - 130.4 (m), 129.9, 129.2, 109.8, 108.9, 96.3, 70.8, 70.8, 70.4, 65.9, 65.8, 25.7, 25.6, 24.7, 24.2.

[0718] HRMS (ESI) calculated for C20H25F5NO7S: 518.1266 [M+H]+, Found: 518.1262.

[0719] Phenyl (Z)-2-((pentafluoro-k6-siilfaneyl)imino)-2-phenylacetate (2af)

[0720] The compound 2af was obtained as a yellowish solid in 63% yield using phenyl 2-diazo-2- phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0721] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 8.04 - 7.95 (m, 2H), 7.76 - 7.68 (m, 1H), 7.63

[0722] - 7.55 (m, 2H), 7.54 - 7.45 (m, 2H), 7.41 - 7.34 (m, 1H), 7.28 - 7.22 (m, 2H).

[0723] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.6 - 76.2 (m), 65.9 - 65.2 (m).

[0724] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 164.1 - 163.5 (m), 162.2, 149.4, 134.8, 130.8 - 130.4 (m), 129.9, 129.5, 129.4, 127.2, 120.8.

[0725] HRMS (ESI) calculated for C14H11F5NO2S: 352.0425 [M+H]+, Found: 352.0432.

[0726] (S)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl (Z)-2-

[0727] ((pentafluoro-k6-siilfaneyl)imino)-2-phenylacetate (lag)

[0728] The compound lag was obtained as a colorless oil in 48% yield using (S)-2,5,7,8-tetramethyl- 2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl 2-diazo-2-phenylacetate following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0729] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.97 - 7.86 (m, 2H), 7.73 - 7.65 (m, 1H), 7.58 - 7.51 (m, 2H), 2.60 (t, J= 6.8 Hz, 2H), 2.10 (s, 3H), 1.97 - 1.88 (m, 6H), 1.81 (q, = 6.9 Hz, 2H), 1.60 - 1.52 (m, 3H), 1.51 - 1.35 (m, 6H), 1.34 - 1.21 (m, 12H), 1.20 - 1.00 (m, 8H), 0.88 (s, 3H), 0.86 (s, 3H), 0.84 (s, 1H).

[0730] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 78.1 - 75.7 (m), 65.7 - 64.8 (m).13C NMR (75 MHz, Methylene Chloride-tfe) 5 165.9 - 165.1 (m), 161.9, 150.1, 139.7, 134.2, 131.4, 129.4, 129.1, 127.1, 125.7, 123.5, 118.1, 75.4, 39.8, 39.4, 37.4, 37.3, 37.3, 32.8, 32.7, 31.0, 28.0, 24.8, 24.4, 23.6, 22.4, 22.4, 21.0, 20.6, 19.5, 19.4, 13.1, 12.2, 11.5.

[0731] HRMS (ESI) calculated for C37H55F5NO3S: 688.3817 [M+H]+, Found: 688.3814.

[0732] (Z)-2-((pentafluoro-k6-sulfaneyl)imino)-l,2-Diphenylethan-l-one (2ah)

[0733] The compound 2ah was obtained as a yellowish oil in 33% yield using 2-diazo-l,2- diphenylethan-l-one following the GP4 after column chromatography on silica gel with hexane / dichloromethane (10 / 1).

[0734] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.97 - 7.75 (m, 4H), 7.70 - 7.58 (m, 2H), 7.54 - 7.42 (m, 4H).

[0735] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 79.8 - 77.4 (m), 68.4 - 67.7 (m).

[0736] 13C NMR (75 MHz, Methylene Chloride-tfe) 5 193.3, 172.4, 172.5 - 172.0 (m), 135.0, 134.3, 133.1 - 132.8 (m), 131.8 - 131.5 (m), 129.5, 129.4, 129.2, 129.1.

[0737] HRMS (ESI) calculated for C14H11F5NOS: 336.0476 [M+H]+, Found: 336.0471.

[0738] 2. Preparation of the SF5-substituted molecules

[0739] 2.1. Under energy transfer catalysis conditions

[0740] General procedure (GP5):

[0741] To a 10 mL tube were sequentially added the styrene compound (0.1 mmol, 1 equiv.), the compound of formula (I) (0.11 mmol, 1.1 equiv.), 9H-thioxanthen-9-one (0.005 mmol, 5 mol%) and Anhydrous ethyl acetate (1 mL, 1 M) under argon atmosphere. The reaction mixture was stirred at room temperature under the irradiation of 405 nm blue light overnight. After completion, the reaction was quenched by saturated brine, then extracted with ethyl acetate (3x 10 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material obtained was then purified by column chromatography on silica gel.

[0742] N-(2-(pentafluoro-k6-sulfaneyl)-l-(p-tolyl)ethyl)-l,l-diphenylmethanimine (4a)

[0743] The compound 4a was obtained as a white solid in 93% yield using l-methyl-4-vinylbenzene following the GP5 after column chromatography on silica gel with toluene.

[0744] 'H NMR (300 MHz, Chloroform-; / ) 5 7.79 - 7.58 (m, 2H), 7.51 - 7.28 (m, 6H), 7.22 - 7.03 (m, 4H), 7.01 - 6.77 (m, 2H), 5.03 - 4.83 (m, 1H), 4.61 - 4.29 (m, 1H), 4.01 - 3.72 (m, 1H), 2.33 (s, 3H).

[0745] 19F NMR (282 MHz, Chloroform-; / ) 5 86.7 - 84.3 (m, IF), 66.6 (dt, J= 146.3, 8.2 Hz, 4F).

[0746] 13C NMR (75 MHz, Chloroform-; / ) 5 169.1, 139.7, 138.5, 137.7, 136.2, 130.3, 130.1, 129.6, 128.8, 128.2, 128.0, 127.7, 127.0, 79.3 - 78.7 (m), 63.4 - 63.1 (m), 21.1.

[0747] HRMS (ESI) calculated for C22H21F5NS: 426.1309 [M+H]+, Found: 426.1310.

[0748] N-(2-(pentafluoro-k6-sulfaneyl)-l-(m-tolyl)ethyl)-l,l-diphenylmethanimine (4b)

[0749] The compound 4b was obtained as a colorless oil in 78% yield using l-methyl-3-vinylbenzene following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (99 / 1).XH NMR (300 MHz, Chloroform-; / ) 5 7.73 - 7.62 (m, 2H), 7.45 - 7.31 (m, 6H), 7.23 - 7.15 (m, 1H), 7.11 - 6.99 (m, 3H), 6.97 - 6.86 (m, 2H), 5.01 - 4.85 (m, 1H), 4.58 - 4.37 (m, 1H), 3.98 - 3.82 (m, 1H), 2.31 (s, 3H).

[0750] 19F NMR (282 MHz, Chloroform-; / ) 5 86.67 - 84.35 (m, IF), 66.54 (dt, J= 146.4, 8.1 Hz, 4F).13C NMR (75 MHz, Chloroform-; / ) 5 169.2, 141.5, 139.8, 138.6, 136.3, 130.3, 128.8, 128.8, 128.7, 128.7, 128.2, 128.0, 127.8, 127.7, 124.1, 79.3 - 78.7 (m), 63.6 - 62.9 (m), 30.9, 21.4. HRMS (ESI) calculated for C22H21F5NS: 426.1309 [M+H]+, Found: 426.1315.

[0751] N-(2-(pentafluoro-k6-sulfaneyl)-l-(o-tolyl)ethyl)-l,l-diphenylmethanimine (4c)

[0752] The compound 4c was obtained as a white solid in 95% yield using l-methyl-2-vinylbenzene following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (99 / 1). 'H NMR (300 MHz, Chloroform-; / ) 5 7.83 - 7.64 (m, 2H), 7.62 - 7.49 (m, 1H), 7.48 - 7.26 (m, 6H), 7.22 - 7.02 (m, 3H), 6.98 - 6.70 (m, 2H), 5.20 - 5.02 (m, 1H), 4.60 - 4.36 (m, 1H), 3.86 - 3.62 (m, 1H), 1.86 (s, 3H).

[0753] 19F NMR (282 MHz, Chloroform-; / ) 5 86.6 - 84.3 (m, IF), 65.9 (dt, J= 146.2, 8.1 Hz, 4F).

[0754] 13C NMR (75 MHz, Chloroform-; / ) 5 169.3, 140.3, 139.5, 136.8, 134.0, 130.6, 130.3, 128.7, 128.6, 128.4, 128.1, 127.7, 127.6, 127.2, 126.7, 78.3 - 77.7 (m), 59.9 - 59.0 (m), 30.9, 18.6. HRMS (ESI) calculated for C22H21F5NS: 426.1309 [M+H]+, Found: 426.1310.

[0755] N-(l-(4-(tert-butyl)phenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)-l,l-diphenylmethanimine (4d)

[0756] The compound 4d was obtained as a colorless oil in 69% yield using l-(tert-butyl)-4- vinylbenzene following the GP5 after column chromatography on silica gel with pentane / toluene (4 / 1).

[0757] 'H NMR (300 MHz, Chloroform-; / ) 5 7.71 - 7.60 (m, 2H), 7.50 - 7.30 (m, 8H), 7.17 (d, J= 8.3 Hz, 2H), 7.02 - 6.87 (m, 2H), 5.02 - 4.84 (m, 1H), 4.60 - 4.34 (m, 1H), 3.96 - 3.79 (m, 1H), 1.30 (s, 9H).

[0758] 19F NMR (282 MHz, Chloroform-^ 5 86.7 - 84.4 (m, IF), 66.6 (dt, J= 146.4, 8.1 Hz, 4F).

[0759] 13C NMR (75 MHz, Chloroform-; / ) 5 168.9, 150.9, 139.8, 138.4, 136.3, 132.4, 130.2, 130.1, 128.8, 128.7, 128.3, 128.2, 128.0, 127.7, 126.8, 125.8, 79.3 - 78.7 (m), 63.3 - 63.0 (m), 34.6, 31.3.

[0760] HRMS (ESI) calculated for C25H27F5NS: 468.1779 [M+H]+, Found: 468.1781.

[0761] 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6-sulfaneyl)ethyl)Phenyl acetate (4e)

[0762] The compound 4e was obtained as a colorless oil in 97% yield using 4-vinylphenyl acetate following the GP5 after column chromatography on silica gel with toluene.

[0763] 'H NMR (300 MHz, Chloroform-; / ) 5 7.75 - 7.60 (m, 2H), 7.52 - 7.31 (m, 6H), 7.29 - 7.23 (m, 2H), 7.10 - 7.00 (m, 2H), 6.98 - 6.84 (m, 2H), 5.04 - 4.88 (m, 1H), 4.56 - 4.32 (m, 1H), 3.98 - 3.77 (m, 1H), 2.29 (s, 3H).

[0764] 19F NMR (282 MHz, Chloroform-; / ) 5 85.8 - 83.5 (m, IF), 66.1 (dt, J= 146.3, 7.6 Hz, 4F).

[0765] 13C NMR (75 MHz, Chloroform-; / ) 5 169.5, 169.3, 150.2, 139.5, 138.9, 136.1, 130.4, 128.8, 128.8, 128.3, 128.2, 128.1, 127.6, 122.1, 79.1 - 78.5 (m), 63.1 - 62.6 (m), 21.1.

[0766] HRMS (ESI) calculated for C23H21F5NO2S: 470.1202 [M+H]+, Found: 470.1208.

[0767] N-(2-(pentafluoro-k6-sulfaneyl)-l-phenylethyl)-l,l-diphenylmethanimine (4f)

[0768] The compound 4f was obtained as a white solid in 90% yield using styrene following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (99 / 1).

[0769] 'H NMR (300 MHz, Chloroform-; / ) 5 7.73 - 7.57 (m, 2H), 7.49 - 7.14 (m, 11H), 7.03 - 6.79

[0770] (m, 2H), 5.07 - 4.86 (m, 1H), 4.57 - 4.34 (m, 1H), 4.01 - 3.78 (m, 1H).

[0771] 19F NMR (282 MHz, Chloroform-^ 5 86.6 - 84.3 (m, IF), 66.6 (dt, J= 146.4, 8.2 Hz, 4F).

[0772] 13C NMR (75 MHz, Chloroform-; / ) 5 169.3, 141.5, 139.7, 136.3, 130.3, 128.9, 128.8, 128.2, 128.1, 127.9, 127.6, 127.2, 79.3 - 78.5 (m), 63.6 - 63.3 (m).

[0773] HRMS (ESI) calculated for C21H19F5NS: 412.1153 [M+H]+, Found: 412.1159.

[0774] N-(l-(naphthalen-2-yl)-2-(pentafluoro-k6-sulfaneyl)ethyl)-l,l-diphenylmethanimine (4g)

[0775] The compound 4g was obtained as a colorless oil in 60% yield using 2-vinylnaphthalene following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (99 / 1).XH NMR (300 MHz, Chloroform-; / ) 5 7.86 - 7.75 (m, 3H), 7.75 - 7.64 (m, 3H), 7.53 - 7.41 (m, 4H), 7.41 - 7.31 (m, 5H), 7.01 - 6.85 (m, 2H), 5.23 - 5.02 (m, 1H), 4.70 - 4.42 (m, 1H), 4.08 - 3.87 (m, 1H).

[0776] 19F NMR (282 MHz, Chloroform-; / ) 5 86.5 - 84.2 (m, IF), 66.7 (dt, J= 146.4, 7.9 Hz, 4F).13C NMR (75 MHz, Chloroform-; / ) 5 169.7, 142.5, 139.6, 138.9, 136.2, 133.5, 133.0, 130.5, 128.9, 128.8, 128.3, 128.1, 128.0, 127.7, 127.6, 126.4, 126.2, 126.2, 124.9, 79.2 - 78.5 (m), 63.7 - 63.5 (m).

[0777] HRMS (ESI) calculated for C25H21F5NS: 462.1309 [M+H]+, Found: 462.1309. N-(l-(4-chlorophenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)-l,l-diphenylmethanimine (4h)

[0778] The compound 4h was obtained as a colorless oil in 89% yield using l-chloro-4-vinylbenzene following the GP5 after column chromatography on silica gel with toluene.

[0779] 'H NMR (300 MHz, Chloroform-; / ) 5 7.74 - 7.57 (m, 2H), 7.51 - 7.26 (m, 8H), 7.22 - 7.14 (m, 2H), 7.01 - 6.81 (m, 2H), 5.02 - 4.84 (m, 1H), 4.53 - 4.26 (m, 1H), 3.93 - 3.76 (m, 1H).

[0780] 19F NMR (282 MHz, Chloroform-; / ) 5 86.2 - 84.0 (m, IF), 66.8 (dt, J= 146.4, 8.2 Hz, 4F).

[0781] 13C NMR (75 MHz, Chloroform-; / ) 5 169.8, 140.0, 139.4, 136.1, 133.7, 130.5, 129.1, 128.9, 128.8, 128.5, 128.3, 128.1, 127.4, 78.8 - 78.4 (m), 62.9 - 62.6 (m).

[0782] HRMS (ESI) calculated for C21H18CIF5NS: 446.0763 [M+H]+, Found: 446.0765.

[0783] N-(l-(4-bromophenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)-l,l-diphenylmethanimine (4i)

[0784] The compound 4i was obtained as a colorless oil in 75% yield using l-bromo-4-vinylbenzene following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (50 / 1).XH NMR (300 MHz, Chloroform-; / ) 5 7.73 - 7.61 (m, 2H), 7.51 - 7.31 (m, 8H), 7.18 - 7.09 (m, 2H), 7.03 - 6.82 (m, 2H), 5.00 - 4.85 (m, 1H), 4.53 - 4.28 (m, 1H), 3.96 - 3.76 (m, 1H).19F NMR (282 MHz, Chloroform-; / ) 5 86.3 - 83.9 (m, IF), 66.8 (dt, J= 146.4, 8.2 Hz, 4F).

[0785] 13C NMR (75 MHz, Chloroform-; / ) 5 169.8, 140.5, 139.4, 136.1, 132.1, 130.5, 128.9, 128.8, 128.8, 128.3, 128.1, 127.4, 121.9, 78.9 - 78.1 (m), 63.0 - 62.7 (m).

[0786] HRMS (ESI) calculated for C2iHi8BrF5NS: 490.0258 [M+H]+, Found: 490.0263.

[0787] N-(l-(4-iodophenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)-l,l-diphenylmethanimine (4j)

[0788] The compound 4j was obtained as a colorless oil in 75% yield using l-iodo-4-vinylbenzene following the GP5 after column chromatography on silica gel with pentane / toluene (4 / 1).

[0789] 'H NMR (300 MHz, Chloroform-; / ) 5 7.73 - 7.57 (m, 4H), 7.49 - 7.29 (m, 6H), 7.08 - 6.96 (m, 2H), 6.95 - 6.80 (m, 2H), 4.99 - 4.79 (m, 1H), 4.54 - 4.26 (m, 1H), 3.94 - 3.77 (m, 1H).19F NMR (282 MHz, Chloroform-; / ) 5 86.3 - 83.9 (m, IF), 66.8 (dt, J= 146.4, 8.1 Hz, 4F).

[0790] 13C NMR (75 MHz, Chloroform-; / ) 5 169.8, 141.2, 139.4, 138.1, 136.1, 132.4, 130.5, 130.1, 129.1, 128.9, 128.8, 128.3, 128.1, 127.5, 93.5, 78.7 - 78.1 (m), 63.1 - 62.8 (m).

[0791] HRMS (ESI) calculated for C21H18F5INS: 538.0119 [M+H]+, Found: 538.0127.

[0792] N-(l-([l,l'-biphenyl]-4-yl)-2-(pentafluoro-k6-sulfaneyl)ethyl)-l,l-diphenylmethanimine (4k)

[0793] The compound 4k was obtained as a colorless oil in 82% yield using 4-vinyl-l,l'-biphenyl following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (50 / 1). 'H NMR (300 MHz, Chloroform-; / ) 5 7.75 - 7.65 (m, 2H), 7.63 - 7.52 (m, 4H), 7.48 - 7.30 (m, 11H), 7.06 - 6.88 (m, 2H), 5.11 - 4.93 (m, 1H), 4.62 - 4.40 (m, 1H), 4.03 - 3.87 (m, 1H).19F NMR (282 MHz, Chloroform-; / ) 5 86.5 - 84.2 (m, IF), 66.7 (dt, J= 146.3, 8.0 Hz, 4F).

[0794] 13C NMR (75 MHz, Chloroform-; / ) 5 169.4, 140.8, 140.5, 139.7, 136.3, 130.4, 128.8, 128.3, 128.1, 127.6, 127.6, 127.5, 127.1, 79.2 - 78.6 (m), 63.4 - 63.1 (m).

[0795] HRMS (ESI) calculated for C27H23F5NS: 488.1466 [M+H]+, Found: 488.1469.

[0796] 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6-sulfaneyl)ethyl)Benzonitrile (41)

[0797] The compound 41 was obtained as a colorless oil in 72% yield using 4-vinylbenzonitrile following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (25 / 1). 'H NMR (300 MHz, Chloroform-; / ) 5 7.78 - 7.56 (m, 4H), 7.53 - 7.28 (m, 8H), 7.03 - 6.75 (m, 2H), 5.09 - 4.90 (m, 1H), 4.53 - 4.27 (m, 1H), 3.99 - 3.76 (m, 1H).

[0798] 19F NMR (282 MHz, Chloroform-; / ) 5 85.7 - 83.4 (m, IF), 67.1 (dt, J= 146.2, 7.7 Hz, 4F).13C NMR (75 MHz, Chloroform-; / ) 5 170.6, 146.6, 139.1, 135.9, 132.8, 130.8, 129.1, 128.8, 128.5, 128.2, 128.1, 127.3, 118.4, 112.0, 78.4 - 77.6 (m), 63.1 - 62.8 (m).

[0799] HRMS (ESI) calculated for C22H18F5N2S: 437.1105 [M+H]+, Found: 437.1105.

[0800] N-(l-(4-nitrophenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)-l,l-diphenylmethanimine (4m)

[0801] The compound 4m was obtained as a colorless oil in 55% yield using l-nitro-4-vinylbenzene following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (20 / 1). 'H NMR (300 MHz, Chloroform-; / ) 5 8.27 - 8.06 (m, 2H), 7.69 - 7.61 (m, 2H), 7.50 - 7.31 (m, 8H), 6.95 - 6.79 (m, 2H), 5.12 - 4.99 (m, 1H), 4.53 - 4.30 (m, 1H), 3.99 - 3.81 (m, 1H).19F NMR (282 MHz, Chloroform-; / ) 5 85.6 - 83.3 (m, IF), 67.2 (dt, J= 146.3, 7.8 Hz, 4F).

[0802] 13C NMR (75 MHz, Chloroform-; / ) 5 170.8, 148.5, 147.6, 139.0, 135.9, 130.9, 129.2, 128.9, 128.5, 128.2, 127.2, 124.2, 78.2 - 77.6 (m), 62.9 - 62.6 (m).

[0803] HRMS (ESI) calculated for C21H18F5N2O2S: 457.1004 [M+H]+, Found: 457.1010.

[0804] 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6-siilfaneyl)ethyl)Benzaldehyde (4n)

[0805] The compound 4n was obtained as a colorless oil in 83% yield using 4-vinylbenzaldehyde following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (50 / 1). 'H NMR (300 MHz, Chloroform-; / ) 5 10.00 (s, 1H), 7.88 - 7.79 (m, 2H), 7.72 - 7.63 (m, 2H), 7.51 - 7.31 (m, 8H), 6.97 - 6.77 (m, 2H), 5.09 - 4.97 (m, 1H), 4.55 - 4.34 (m, 1H), 3.99 - 3.81 (m, 1H).

[0806] 19F NMR (282 MHz, Chloroform-; / ) 5 85.9 - 83.6 (m, IF), 67.3 - 66.6 (m, 4F).

[0807] 13C NMR (75 MHz, Chloroform-; / ) 5 191.7, 170.3, 148.0, 139.2, 136.0, 130.7, 130.3, 129.0, 128.8, 128.4, 128.2, 127.9, 127.4, 78.5 - 77.9 (m), 63.4 - 63.1 (m), .

[0808] HRMS (ESI) calculated for C22H19F5NOS: 440.1102 [M+H]+, Found: 440.1104.

[0809] N-(2-(pentafluoro-k6-suifaneyl)-l,l-diphenylethyl)-l,l-diphenylmethanimine (4o)

[0810] The compound 4o was obtained as a white solid in 98% yield using ethene- 1,1-diyldibenzene following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (25 / 1). 'H NMR (300 MHz, Chloroform-; / ) 5 7.78 - 7.64 (m, 2H), 7.46 - 7.33 (m, 3H), 7.25 - 7.09 (m, 10H), 7.07 - 6.98 (m, 2H), 6.60 - 6.42 (m, 2H), 4.73 (p, J= 7.8 Hz, 2H).19F NMR (282 MHz, Chloroform-; / ) 5 87.5 - 85.2 (m, IF), 74.7 - 73.8 (m, 4F).

[0811] 13C NMR (75 MHz, Chloroform-; / ) 5 169.1, 147.1, 141.8, 137.9, 130.3, 128.6, 128.0, 128.0, 127.6, 127.4, 127.1, 127.0, 126.4, 81.0 - 80.3 (m), 67.0.

[0812] HRMS (ESI) calculated for C27H23F5NS: 488.1466 [M+H]+, Found: 488.1470.

[0813] N-(l-(pentafluoro-k6-sulfaneyl)-2-phenylpropan-2-yl)-l,l-diphenylmethanimine (4p)

[0814] The compound 4p was obtained as a white solid in 78% yield using prop-l-en-2-ylbenzene following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (99 / 1). 'H NMR (300 MHz, Chloroform-; / ) 5 7.73 - 7.54 (m, 2H), 7.42 - 7.24 (m, 8H), 7.18 - 7.02 (m, 2H), 6.57 (s, 2H), 4.64 - 4.43 (m, 1H), 4.03 - 3.83 (m, 1H).

[0815] 19F NMR (282 MHz, Chloroform-; / ) 5 88.3 - 86.0 (m, IF), 70.4 (dt, J= 146.0, 8.1 Hz, 4F).13C NMR (75 MHz, Chloroform-; / ) 5 166.7, 146.3, 141.2, 138.5, 130.1, 128.5, 128.5, 128.0, 127.9, 127.8, 127.5, 127.4, 126.5, 86.7 - 86.3 (m), 64.4, 23.8.

[0816] HRMS (ESI) calculated for C22H21F5NS: 426.1309 [M+H]+, Found: 426.1312.

[0817] N-(2-(pentafluoro-k6-sulfaneyl)-l-(thiophen-2-yl)ethyl)-l,l-diphenylmethanimine (4q)

[0818] F5S ry

[0819] S NCPh2

[0820] The compound 4q was obtained as a yellowish oil in 68% yield using 2-vinylthiophene following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (50 / 1).XH NMR (300 MHz, Chloroform-; / ) 5 7.78 - 7.57 (m, 2H), 7.53 - 7.30 (m, 6H), 7.26 - 7.21 (m, 1H), 7.14 - 6.92 (m, 3H), 6.88 - 6.79 (m, 1H), 5.39 - 5.20 (m, 1H), 4.57 - 4.31 (m, 1H), 4.06 - 3.83 (m, 1H).

[0821] 19F NMR (282 MHz, Chloroform-; / ) 5 86.2 - 83.8 (m, IF), 66.8 (dt, J= 146.6, 8.1 Hz, 4F).13C NMR (75 MHz, Chloroform-; / ) 5 170.0, 143.8, 139.4, 135.7, 130.6, 128.9, 128.3, 128.1, 127.6, 126.7, 125.3, 124.0, 79.1 - 78.6 (m), 59.5 - 59.1 (m).

[0822] HRMS (ESI) calculated for C19H17F5NS2: 418.0717 [M+H]+, Found: 418.0714.

[0823] (lS,2R,5S)-2-isopropyl-5-methylcyclohexyl 4-(l-((diphenylmethylene)amino)-2- (pentafluoro-k -sulfaneyl)ethyl)benzoate (4r)

[0824] The compound 4r was obtained as a yellowish oil in 80% yield using (lS,2R,5S)-2-isopropyl- 5-methylcyclohexyl 4-vinylbenzoate following the GP5 after column chromatography on silica gel with toluene.

[0825] 'H NMR (300 MHz, Chloroform-; / ) 5 8.06 - 7.94 (m, 2H), 7.73 - 7.61 (m, 2H), 7.48 - 7.29 (m, 8H), 7.00 - 6.82 (m, 2H), 5.08 - 4.86 (m, 2H), 4.55 - 4.34 (m, 1H), 3.98 - 3.79 (m, 1H), 2.18 - 2.04 (m, 1H), 2.01 - 1.87 (m, 1H), 1.78 - 1.68 (m, 2H), 1.62 - 1.52 (m, 2H), 1.19 - 1.04 (m, 2H), 0.99 - 0.87 (m, 7H), 0.84 - 0.72 (m, 3H).

[0826] 19F NMR (282 MHz, Chloroform-; / ) 5 86.1 - 83.8 (m, IF), 66.9 (dq, J= 146.1, 7.6 Hz, 4F).

[0827] 13C NMR (75 MHz, Chloroform-; / ) 5 169.9, 165.7, 165.6, 146.2, 139.4, 136.1, 130.6, 130.5, 130.2, 130.2, 128.9, 128.8, 128.4, 128.1, 127.5, 127.2, 78.6 - 78.1 (m), 75.0, 63.4 - 63.1 (m), 47.3, 47.3, 41.0, 34.3, 31.5, 26.6, 23.7, 22.0, 20.8, 20.7, 16.6.

[0828] HRMS (ESI) calculated for C32H37F5NO2S: 594.2460 [M+H]+, Found: 594.2454.

[0829] ((S)-4-(prop-l-en-2-yl)cyclohex-l-en-l-yl)Methyl 4-(l-((diphenylmethylene)amino)-2-

[0830] (pentafluoro-k6-sulfaneyl)ethyl)benzoate (4s)

[0831] The compound 4s was obtained as a colorless oil in 97% yield using (S)-(4-(prop-l-en-2- yl)cyclohex-l-en-l-yl)methyl 4-vinylbenzoate following the GP5 after column chromatography on silica gel with toluene.

[0832] 'H NMR (300 MHz, Chloroform-; / ) 5 8.12 - 7.92 (m, 2H), 7.74 - 7.59 (m, 2H), 7.51 - 7.28 (m, 8H), 7.04 - 6.77 (m, 2H), 5.84 (s, 1H), 5.07 - 4.94 (m, 1H), 4.83 - 4.64 (m, 4H), 4.56 - 4.33 (m, 1H), 3.99 - 3.78 (m, 1H), 2.30 - 2.09 (m, 4H), 2.08 - 1.95 (m, 1H), 1.93 - 1.81 (m, 1H), 1.74 (s, 3H), 1.60 - 1.44 (m, 1H).

[0833] 19F NMR (282 MHz, Chloroform-; / ) 5 86.1 - 83.8 (m, IF), 66.9 (dt, J= 146.3, 8.1 Hz, 4F).

[0834] 13C NMR (75 MHz, Chloroform-; / ) 5 170.0, 166.0, 149.5, 146.4, 139.4, 136.1, 132.6, 130.6, 130.3, 130.1, 128.9, 128.8, 128.4, 128.1, 127.4, 127.2, 125.8, 108.8, 78.8 - 78.0 (m), 69.0, 63.3 - 63.1 (m), 40.9, 30.5, 27.4, 26.5, 20.8.

[0835] HRMS (ESI) calculated for C22H21F5NS: 590.2147 [M+H]+, Found: 590.2164.

[0836] ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6- sulfaneyl)ethyl)benzoate (4t)

[0837] The compound 4t was obtained as a colorless oil in 86% yield using ((3aR,5R,5aS,8aS,8bR)- 2,2,7,7-tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl 4- vinylbenzoate following the GP5 after column chromatography on silica gel with toluene / ethyl acetate (9 / 1).

[0838] 'H NMR (300 MHz, Chloroform-; / ) 5 8.06 - 7.92 (m, 2H), 7.73 - 7.59 (m, 2H), 7.47 - 7.29 (m, 8H), 7.00 - 6.79 (m, 2H), 5.62 - 5.53 (m, 1H), 5.06 - 4.92 (m, 1H), 4.68 - 4.61 (m, 1H), 4.55 - 4.38 (m, 3H), 4.37 - 4.29 (m, 2H), 4.22 - 4.14 (m, 1H), 3.96 - 3.79 (m, 1H), 1.51 (d, = 2.9 Hz, 3H), 1.47 (s, 3H), 1.35 (s, 3H), 1.34 - 1.30 (m, 3H).

[0839] 19F NMR (282 MHz, Chloroform-; / ) 5 86.1 - 83.8 (m, IF), 66.8 (dt, J= 146.4, 7.8 Hz, 4F).

[0840] 13C NMR (75 MHz, Chloroform-; / ) 5 170.1, 170.1, 170.1, 166.0, 146.5, 139.3, 136.0, 130.6, 130.4, 129.8, 128.9, 128.8, 128.4, 128.1, 127.4, 127.2, 109.7, 108.8, 96.3, 78.7 - 78.0 (m), 71.2, 70.8, 70.6, 66.2, 66.1, 64.1, 64.1, 63.3 - 63.1 (m), 26.0, 26.0, 26.0, 25.0, 24.5.

[0841] HRMS (ESI) calculated for C34H37F5NO7S: 698.2205 [M+H]+, Found: 698.2197.

[0842] 2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(l-

[0843] ((diphenylmethylene)amino)-2-(pentafluoro-k6-sulfaneyl)ethyl)benzoate (4u)

[0844] The compound 4u was obtained as a colorless oil in 75% yield using 2-((lR,5S)-6,6- dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl 4-vinylbenzoate following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (20 / 1). 'H NMR (300 MHz, Chloroform-; / ) 5 8.03 - 7.91 (m, 2H), 7.73 - 7.60 (m, 2H), 7.46 - 7.28 (m, 8H), 6.95 - 6.80 (m, 2H), 5.35 (s, 1H), 5.04 - 4.94 (m, 1H), 4.51 - 4.37 (m, 1H), 4.37 - 4.27 (m, 2H), 3.95 - 3.80 (m, 1H), 2.47 - 2.34 (m, 3H), 2.30 - 2.17 (m, 2H), 2.10 (d, J= 5.1 Hz, 2H), 1.26 (s, 3H), 1.16 (d, J= 8.5 Hz, 1H), 0.85 - 0.81 (m, 3H).

[0845] 19F NMR (282 MHz, Chloroform-; / ) 5 86.1 - 83.8 (m, IF), 66.9 (dt, J= 146.3, 7.3 Hz, 4F).

[0846] 13C NMR (75 MHz, Chloroform-; / ) 5 170.0, 166.1, 146.3, 144.2, 139.4, 136.1, 130.6, 130.2, 128.9, 128.8, 128.3, 128.1, 127.4, 127.2, 119.0, 78.7 - 78.0 (m), 63.4, 63.4, 63.3 - 63.1 (m), 45.8, 40.8, 38.0, 36.1, 31.7, 31.4, 26.3, 21.2.

[0847] HRMS (ESI) calculated for C33H35F5NO2S: 604.2303 [M+H]+, Found: 604.2301.

[0848] (S)-3,7-dimethyloct-6-en-l-yl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6- sulfaneyl)ethyl)Benzoate (4v)

[0849] The compound 4v was obtained as a colorless oil in 78% yield using (S)-3,7-dimethyloct-6-en- 1-yl 4-vinylbenzoate following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (20 / 1).

[0850] 'H NMR (300 MHz, Chloroform-; / ) 5 8.03 - 7.92 (m, 2H), 7.74 - 7.59 (m, 2H), 7.48 - 7.28 (m, 8H), 6.97 - 6.77 (m, 2H), 5.09 (t, J= 6.6 Hz, 1H), 4.99 (d, J= 9.4 Hz, 1H), 4.52 - 4.28 (m, 3H), 3.98 - 3.78 (m, 1H), 2.08 - 1.92 (m, 2H), 1.86 - 1.74 (m, 1H), 1.72 - 1.46 (m, 9H), 1.46 - 1.34 (m, 1H), 1.28 - 1.18 (m, 1H), 0.96 (d, J= 6.2 Hz, 3H).

[0851] 19F NMR (282 MHz, Chloroform-; / ) 5 86.1 - 83.8 (m, IF), 66.9 (dt, J= 146.3, 8.0 Hz, 4F).

[0852] 13C NMR (75 MHz, Chloroform-; / ) 5 170.0, 166.2, 146.3, 139.3, 136.1, 131.4, 130.6, 130.2, 128.9, 128.8, 128.4, 128.1, 127.4, 127.2, 124.5, 78.6 - 78.0 (m), 63.6, 63.3 - 63.1 (m), 37.0, 35.5, 29.6, 25.7, 25.4, 19.5, 17.7.

[0853] HRMS (ESI) calculated for C32H37F5NO2S: 594.2460 [M+H]+, Found: 594.2456.

[0854] 4- F ormyl-2-methoxyphenyl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6- sulfaneyl)ethyl)benzoate (4w) The compound 4w was obtained as a white solid in 87% yield using 4-formyl-2-methoxyphenyl 4-vinylbenzoate following the GP5 after column chromatography on silica gel with pentane / ethyl acetate (50 / 1).

[0855] 'H NMR (300 MHz, Chloroform-; / ) 5 9.98 (s, 1H), 8.25 - 8.10 (m, 2H), 7.76 - 7.63 (m, 2H), 7.57 - 7.51 (m, 2H), 7.49 - 7.31 (m, 9H), 7.03 - 6.86 (m, 2H), 5.13 - 4.99 (m, 1H), 4.57 - 4.35 (m, 1H), 3.89 (s, 4H).

[0856] 19F NMR (282 MHz, Chloroform-^ 5 86.0 - 83.7 (m, IF), 67.0 (dt, J= 146.4, 8.1 Hz, 4F).

[0857] 13C NMR (75 MHz, Chloroform-; / ) 5 191.0, 170.2, 163.7, 152.2, 147.4, 145.1, 139.3, 136.0, 135.4, 131.1, 130.7, 129.0, 128.9, 128.5, 128.4, 128.2, 127.5, 127.4, 124.8, 123.5, 110.9, 78.5 - 78.0 (m), 63.4 - 63.1 (m), 56.2.

[0858] HRMS (ESI) calculated for C30H25F5NO4S: 590.1419 [M+H]+, Found: 590.1424.

[0859] (8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,ll,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6- sulfaneyl)ethyl)benzoate (4x)

[0860] The compound 4x was obtained as a yellowish oil in 91% yield using (8R,9S,13S,14S)-13- methyl-17-oxo-7,8,9,ll,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 4- vinylbenzoate following the GP5 after column chromatography on silica gel with toluene / ethyl acetate (20 / 1).

[0861] XH NMR (300 MHz, Chloroform-; / ) 5 8.25 - 8.01 (m, 2H), 7.77 - 7.61 (m, 2H), 7.54 - 7.28 (m, 9H), 7.07 - 6.81 (m, 4H), 5.18 - 4.90 (m, 1H), 4.62 - 4.34 (m, 1H), 4.06 - 3.81 (m, 1H), 3.05 - 2.83 (m, 2H), 2.57 - 2.46 (m, 1H), 2.45 - 2.25 (m, 2H), 2.22 - 1.92 (m, 4H), 1.71 - 1.41 (m, 6H), 0.92 (s, 3H).

[0862] 19F NMR (282 MHz, Chloroform-; / ) 5 86.1 - 83.8 (m, IF), 67.0 (dt, J= 146.4, 7.4 Hz, 4F).

[0863] 13C NMR (75 MHz, Chloroform-; / ) 5 170.2, 165.0, 148.8, 147.1, 139.3, 138.1, 137.6, 136.1, 130.8, 130.6, 130.1, 129.4, 129.0, 128.8, 128.4, 128.3, 128.1, 127.4, 126.5, 121.6, 118.8, 78.6 - 78.0 (m), 63.3 - 63.1 (m), 50.5, 48.0, 44.2, 38.1, 35.9, 31.6, 29.7, 29.4, 26.4, 25.8, 21.6, 13.9. HRMS (ESI) calculated for C40H39F5NO3S: 708.2565 [M+H]+, Found: 708.2572. (R)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl 4 (1-

[0864] ((diphenylmethylene)amino)-2-(pentafluoro-k6-sulfaneyl)ethyl)benzoate (4y)

[0865] The compound 4y was obtained as a colorless oil in 45% yield using (R)-2,5,7,8-tetramethyl- 2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl 4-vinylbenzoate following the GP5 after column chromatography on silica gel with toluene.

[0866] 'H NMR (300 MHz, Chloroform-; / ) 5 8.26 - 8.11 (m, 2H), 7.76 - 7.61 (m, 2H), 7.54 - 7.29 (m, 8H), 7.04 - 6.86 (m, 2H), 5.11 - 4.97 (m, 1H), 4.58 - 4.33 (m, 1H), 4.03 - 3.83 (m, 1H), 2.61 (t, J= 6.5 Hz, 2H), 2.11 (s, 3H), 2.08 - 1.95 (m, 6H), 1.89 - 1.71 (m, 2H), 1.60 (s, 1H), 1.54 - 1.47 (m, 2H), 1.44 - 0.95 (m, 21H), 0.93 - 0.78 (m, 12H).

[0867] 19F NMR (282 MHz, Chloroform-; / ) 5 86.0 - 83.8 (m, IF), 67.0 (dt, J= 146.2, 7.9 Hz, 4F).

[0868] 13C NMR (75 MHz, Chloroform-; / ) 5 170.1, 164.7, 149.5, 146.9, 140.6, 139.4, 136.1, 130.8, 130.6, 129.3, 129.0, 128.8, 128.4, 128.1, 127.5, 126.8, 125.1, 123.2, 117.5, 78.7 - 77.9 (m), 75.1, 63.4 - 63.1 (m), 39.4, 37.5, 37.3, 32.8, 32.7, 32.7, 28.0, 24.8, 24.5, 23.7, 22.7, 22.6, 21.1, 20.7, 19.8, 19.7, 13.1, 12.2, 11.9.

[0869] HRMS (ESI) calculated for C51H67F5NO3S: 868.4756 [M+H]+, Found: 868.4754.

[0870] 2.2. Under single-electron transfer conditions

[0871] General procedure (GP6):

[0872] To a 10 mL tube were sequentially added the styrene compound (0.2 mmol, 1 equiv.), the compound of formula (I) (0.26 mmol, 1.3 equiv.), diethyl 2,6-dimethyl-l,4-dihydropyridine- 3,5-dicarboxylate (2.0 mmol, 5.0 equiv.), [Ir(dF(CF3)ppy)2dtbbpy]PFe (1 mol%), 4 M HC1 (20 pL, 0.4 eq) and Toluene (2 mL, 1 M) under argon atmosphere. The reaction mixture was stirred at room temperature under the irradiation of 455 nm blue light overnight. After completion, the reaction was quenched by saturated brine, then extracted with ethyl acetate (3^ 10 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material obtained was then purified by column chromatography on silica gel. (4-(tert-butyl)phenethyl)Pentafluoro-k6-sulfane (5b)

[0873] The compound 5b was obtained as a colorless oil in 72% yield using l-(tert-butyl)-4- vinylbenzene following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (35 / 1).

[0874] 'H NMR (300 MHz, Chloroform-; / ) 5 7.39 - 7.30 (m, 2H), 7.16 - 7.07 (m, 2H), 3.94 - 3.76 (m, 2H), 3.23 - 3.14 (m, 2H), 1.30 (s, 9H).

[0875] 19F NMR (282 MHz, Chloroform-; / ) 5 85.9 - 83.8 (m, IF), 63.7 (dt, J= 144.9, 8.0 Hz, 4F).

[0876] 13C NMR (75 MHz, Chloroform-; / ) 5 150.3, 133.7, 128.3, 125.9, 73.0 - 72.3 (m), 34.5, 32.1 - 31.8 (m), 31.3.

[0877] HRMS (APCI) calculated for C12H17F5S: 288.0966 [M]+, Found: 288.0964.

[0878] (4-(chloromethyl)phenethyl)Pentafluoro-k6-siilfane (5e)

[0879] The compound 5e was obtained as a colorless oil in 68% yield using l-chloro-4-vinylbenzene following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (35 / 1).

[0880] 'H NMR (300 MHz, Chloroform-; / ) 5 7.40 - 7.32 (m, 2H), 7.24 - 7.14 (m, 2H), 4.56 (s, 2H), 3.94 - 3.76 (m, 2H), 3.30 - 3.16 (m, 2H).

[0881] 19F NMR (282 MHz, Chloroform-; / ) 5 85.7 - 83.3 (m, IF), 63.9 (dt, J= 145.0, 7.9 Hz, 4F).

[0882] 13C NMR (75 MHz, Chloroform-; / ) 5 137.1, 136.6, 129.2, 129.0, 72.3 (p, J = 12.6, 12.1 Hz), 45.7, 32.4 - 31.9 (m), 29.7.

[0883] HRMS (APCI) calculated for C9H10F5S: 245.0418 [M]+, Found: 245.0418.

[0884] Pentafluoro(4-iodophenethyl)- / J’-siilfane (5h)

[0885] The compound 5h was obtained as a colorless oil in 63% yield using l-iodo-4-vinylbenzene following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (35 / 1).XH NMR (300 MHz, Chloroform-; / ) 5 7.75 - 7.56 (m, 2H), 7.02 - 6.86 (m, 2H), 3.92 - 3.74 (m, 2H), 3.22 - 3.09 (m, 2H).

[0886] 19F NMR (282 MHz, Chloroform-; / ) 5 85.5 - 83.3 (m, IF), 64.0 (dt, J= 145.0, 7.9 Hz, 4F).

[0887] 13C NMR (75 MHz, Chloroform-; / ) 5 138.1, 136.4, 130.5, 92.6, 72.4 - 71.5 (m), 32.2 - 31.6 (m).

[0888] HRMS (APCI) calculated for C8H8F5IS: 357.9306 [M]+, Found: 357.9298.

[0889] (2-([l,l'-biphenyl]-4-yl)ethyl)Pentafluoro-k6-sulfane (5j)

[0890] The compound 5j was obtained as a colorless oil in 68% yield using 4-vinyl-l,l'-biphenyl following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (35 / 1).

[0891] 'H NMR (300 MHz, Chloroform-; / ) 5 7.60 - 7.50 (m, 4H), 7.48 - 7.40 (m, 2H), 7.38 - 7.31 (m, 1H), 7.31 - 7.25 (m, 2H), 3.99 - 3.81 (m, 2H), 3.33 - 3.17 (m, 2H).

[0892] 19F NMR (282 MHz, Chloroform-; / ) 5 85.8 - 83.6 (m, IF), 63.8 (dt, J= 144.9, 8.0 Hz, 4F).

[0893] 13C NMR (75 MHz, Chloroform-; / ) 5 140.5, 140.3, 135.8, 129.0, 128.8, 127.7, 127.4, 127.0, 73.1 - 71.9 (m), 32.4 - 31.9 (m).

[0894] HRMS (APCI) calculated for C14H13F5S: 308.0653 [M]+, Found: 308.0652.

[0895] (lS,2R,5S)-2-Isopropyl-5-methylcyclohexyl 4-(2-(pentafluoro-k6-sulfaneyl)ethyl)benzoate

[0896] (5k)

[0897] The compound 5k was obtained as a colorless oil in 61% yield using (lS,2R,5S)-2-isopropyl- 5-methylcyclohexyl 4-vinylbenzoate following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (10 / 1).

[0898] 'H NMR (300 MHz, Chloroform-; / ) 5 8.04 - 7.94 (m, 2H), 7.30 - 7.25 (m, 2H), 4.96 - 4.86 (m, 1H), 3.99 - 3.74 (m, 2H), 3.38 - 3.15 (m, 2H), 2.15 - 2.07 (m, 1H), 1.98 - 1.88 (m, 1H), 1.76 - 1.68 (m, 2H), 1.60 - 1.50 (m, 3H), 1.18 - 1.04 (m, 2H), 0.93 - 0.88 (m, 6H), 0.80 - 0.72 (m, 3H).

[0899] 19F NMR (282 MHz, Chloroform-; / ) 5 85.4 - 83.3 (m, IF), 64.0 (dt, J= 145.0, 7.8 Hz, 4F).

[0900] 13C NMR (75 MHz, Chloroform-; / ) 5 165.6, 141.7, 130.2, 75.0, 72.3 - 71.6 (m), 47.3, 41.0, 34.3, 32.6 - 32.2 (m), 31.5, 26.6, 23.7, 22.0, 20.7, 16.6.

[0901] HRMS (ESI) calculated for C19H28F5O2S: 415.1725 [M+H]+, Found: 415.1723.

[0902] (S)-(4-(prop-l-en-2-yl)cyclohex-l-en-l-yl)Methyl 4-(2-(pentafluoro-k6- sulfaneyl)ethyl)benzoate (51)

[0903] The compound 51 was obtained as a colorless oil in 54% yield using (S)-(4-(prop-l-en-2- yl)cyclohex-l-en-l-yl)methyl 4-vinylbenzoate following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (10 / 1).

[0904] 'H NMR (300 MHz, Chloroform-; / ) 5 8.01 (d, J= 8.3 Hz, 2H), 7.27 (d, J= 8.2 Hz, 2H), 5.84 (s, 1H), 4.78 - 4.60 (m, 4H), 3.97 - 3.77 (m, 2H), 3.34 - 3.19 (m, 2H), 2.26 - 2.08 (m, 4H), 2.07 - 1.95 (m, 1H), 1.94 - 1.83 (m, 1H), 1.74 (s, 3H), 1.56 - 1.46 (m, 1H).

[0905] 19F NMR (282 MHz, Chloroform-; / ) 5 85.3 - 83.1 (m, IF), 64.1 (dt, J= 145.0, 7.7 Hz, 4F).

[0906] 13C NMR (75 MHz, Chloroform-; / ) 5 166.0, 149.5, 141.9, 132.6, 130.3, 129.6, 128.6, 125.8, 108.8, 72.1 - 71.6 (m), 68.9, 40.9, 32.6 - 32.2 (m), 30.5, 27.3, 26.5, 20.7.

[0907] HRMS (ESI) calculated for C19H24F5O2S: 411.1412 [M+H]+, Found: 411.1413.

[0908] ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d] pyran-5-yl)methyl 4-(2-(pentafluoro-k6-sidfaneyl)ethyl)benzoate (5m)

[0909] The compound 5m was obtained as a colorless oil in 45% yield using ((3aR,5R,5aS,8aS,8bR)-

[0910] 2,2,7,7-tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl vinylbenzoate following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (10 / 1).

[0911] XH NMR (300 MHz, Chloroform-; / ) 5 8.05 - 7.95 (m, 2H), 7.29 - 7.24 (m, 2H), 5.55 (d, J= 5.0 Hz, 1H), 4.69 - 4.59 (m, 1H), 4.56 - 4.37 (m, 2H), 4.36 - 4.28 (m, 2H), 4.22 - 4.11 (m, 1H), 3.97 - 3.77 (m, 2H), 3.38 - 3.16 (m, 2H), 1.50 (s, 3H), 1.47 (s, 3H), 1.35 (s, 3H), 1.32 (s, 3H).19F NMR (282 MHz, Chloroform-; / ) 5 85.4 - 83.0 (m, IF), 64.1 (dt, J= 144.9, 7.7 Hz, 4F).

[0912] 13C NMR (75 MHz, Chloroform-; / ) 5 166.0, 142.0, 130.4, 129.2, 128.6, 109.7, 108.8, 96.3, 72.2 - 71.4 (m), 71.2, 70.7, 70.5, 66.2, 64.0, 32.6 - 32.2 (m), 29.7, 26.0, 26.0, 25.0, 24.5.

[0913] HRMS (ESI) calculated for C12H17F5S: 519.1470 [M+H]+, Found: 519.1470.

[0914] 2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(2-(pentafluoro-k6- sulfaneyl)ethyl)benzoate (5n)

[0915] The compound 5n was obtained as a colorless oil in 58% yield using 2-((lR,5S)-6,6- dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl 4-vinylbenzoate following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (10 / 1).

[0916] XH NMR (300 MHz, Chloroform-; / ) 5 8.04 - 7.86 (m, 2H), 7.31 - 7.25 (m, 2H), 5.39 - 5.30 (m, 1H), 4.38 - 4.24 (m, 2H), 3.96 - 3.77 (m, 2H), 3.32 - 3.20 (m, 2H), 2.46 - 2.33 (m, 3H), 2.31 - 2.15 (m, 2H), 2.13 - 2.02 (m, 2H), 1.26 (s, 3H), 1.16 (d, J= 8.5 Hz, 1H), 0.82 (s, 3H).

[0917] 19F NMR (282 MHz, Chloroform-; / ) 5 85.4 - 83.1 (m, IF), 64.0 (dt, J= 144.8, 7.8 Hz, 4F).

[0918] 13C NMR (75 MHz, Chloroform-; / ) 5 166.1, 144.2, 141.8, 130.2, 129.6, 128.6, 119.0, 72.4 - 71.3 (m), 63.4, 45.8, 40.8, 38.0, 36.1, 32.5 - 32.2 (m), 31.7, 31.4, 26.3, 21.1.

[0919] HRMS (ESI) calculated for C19H28F5O2S: 415.1725 [M+H]+, Found: 415.1723.

[0920] (S)-3,7-Dimethyloct-6-en-l-yl 4-(2-(pentafluoro-k6-sulfaneyl)ethyl)benzoate (5o)

[0921] The compound 5o was obtained as a colorless oil in 53% yield using (S)-3,7-dimethyloct-6-en- 1-yl 4-vinylbenzoate following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (10 / 1).

[0922] 'H NMR (300 MHz, Chloroform-; / ) 5 7.99 (d, J= 8.1 Hz, 2H), 7.26 (d, J= 8.6 Hz, 2H), 5.08 (t, J = 6.6 Hz, 1H), 4.34 (t, J = 5.5 Hz, 2H), 3.97 - 3.76 (m, 2H), 3.34 - 3.14 (m, 2H), 2.08 - 1.90 (m, 2H), 1.86 - 1.75 (m, 1H), 1.66 (s, 3H), 1.58 - 1.47 (m, 3H), 1.44 - 1.35 (m, 1H), 1.28 - 1.19 (m, 2H), 0.96 (d, J= 6.3 Hz, 3H).

[0923] 19F NMR (282 MHz, Chloroform-; / ) 5 85.4 - 83.1 (m, IF), 64.1 (dt, J= 145.0, 7.8 Hz, 4F).

[0924] 13C NMR (75 MHz, Chloroform-; / ) 5 166.2, 141.8, 131.4, 130.2, 129.7, 128.5, 124.5, 72.2 - 71.4 (m), 63.6, 37.0, 35.5, 32.6 - 32.0 (m), 29.6, 25.7, 25.4, 19.5, 17.6.

[0925] HRMS (ESI) calculated for C12H17F5S: 415.1725 [M+H]+, Found: 415.1724.

[0926] 4-Formyl-2-methoxyphenyl 4-(2-(pentafluoro-k6-siilfaneyl)ethyl)benzoate (5p)

[0927] The compound 5p was obtained as a white solid in 46% yield using 4-formyl-2-methoxyphenyl 4-vinylbenzoate following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (10 / 1).

[0928] 'H NMR (300 MHz, Chloroform-; / ) 5 9.98 (s, 1H), 8.22 - 8.11 (m, 2H), 7.55 - 7.50 (m, 2H), 7.40 - 7.30 (m, 3H), 3.98 - 3.84 (m, 5H), 3.38 - 3.27 (m, 2H).

[0929] 19F NMR (282 MHz, Chloroform-; / ) 5 85.2 - 83.1 (m, IF), 64.2 (dt, J= 145.1, 7.7 Hz, 4F).

[0930] 13C NMR (75 MHz, Chloroform-; / ) 5 191.0, 163.7, 152.2, 145.1, 143.1, 135.3, 131.1, 128.9, 128.0, 124.8, 123.5, 110.9, 72.1 - 71.0 (m), 56.1, 33.0 - 32.0 (m).

[0931] HRMS (APCI) calculated for C12H17F5S: 411.0684 [M]+, Found: 411.0687.

[0932] (8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,ll,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(2-(pentafluoro-k6-sidfaneyl)ethyl)benzoate (5q)

[0933] The compound 5q was obtained as a white solid in 42% yield using (8R,9S,13S,14S)-13- methyl-17-oxo-7,8,9,ll,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 4- vinylbenzoate following the GP6 after column chromatography on silica gel with cyclohexane / ethyl acetate (10 / 1). 'H NMR (300 MHz, Chloroform-; / ) 5 8.19 - 8.09 (m, 2H), 7.38 - 7.28 (m, 3H), 7.00 - 6.90 (m, 2H), 4.02 - 3.81 (m, 2H), 3.37 - 3.23 (m, 2H), 3.01 - 2.85 (m, 2H), 2.58 - 2.46 (m, 1H), 2.45 - 2.37 (m, 1H), 2.37 - 2.26 (m, 1H), 2.22 - 2.10 (m, 1H), 2.09 - 1.94 (m, 3H), 1.71 - 1.37 (m, 7H), 0.92 (s, 3H).

[0934] 19F NMR (282 MHz, Chloroform-; / ) 5 85.4 - 83.0 (m, IF), 64.2 (dt, J= 145.0, 7.7 Hz, 4F).13C NMR (75 MHz, Chloroform-; / ) 5 165.0, 148.8, 142.7, 138.1, 137.6, 130.8, 128.8, 128.8, 126.5, 121.6, 118.8, 50.5, 48.0, 44.2, 38.0, 35.9, 31.6, 29.4, 26.4, 25.8, 21.6, 13.9.

[0935] HRMS (ESI) calculated for C27H30F5O3S: 529.1830 [M+H]+, Found: 529.1824.

[0936] 2.3. Azabicyclobutanyl series

[0937] General procedure (GP7):

[0938] To a 10 mL tube were sequentially added the azabicyclobutanyl compound (0.15 mmol, 1.5 equiv.), the compound of formula (I) (0.1 mmol, 1.0 equiv.), 9H-thioxanthen-9-one (0.005 mmol, 5 mol%) and anhydrous ethyl acetate (1 mL, 1 M) under argon atmosphere. The reaction mixture was stirred at room temperature under the irradiation of 405 nm blue light overnight. After completion, the reaction was quenched by saturated brine, then extracted with ethyl acetate (3^ 10 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material obtained was then purified by column chromatography on silica gel.

[0939] A-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l,l-diphenylmethanimine (3a)

[0940] The compound 3a was obtained as a white solid in 73% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (100 : 1).

[0941] XH NMR (300 MHz, Chloroform-; / ) 5 7.72 - 7.59 (m, 2H), 7.49 - 7.40 (m, 3H), 7.37 - 7.17 (m, 8H), 6.82 - 6.69 (m, 2H), 4.26 (d, J= 7.95 Hz, 2H), 3.79 (d, J= 8.04 Hz, 2H).

[0942] 19F NMR (282 MHz, Chloroform-; / ) 5 93.0 - 72.3 (m, IF), 52.7 (d, J= 154.77 Hz, 4F).

[0943] 13C NMR (75 MHz, Chloroform-; / ) 5 168.0, 145.2, 139.6, 137.0, 130.6, 129.2, 128.8, 128.6, 128.2, 128.1, 127.9, 127.2, 125.3, 68.9 - 68.5 (m), 60.3.

[0944] HRMS (ESI) calculated for C22H20F5N2S: 439.1262 [M+H]+, Found: 439.1262. l,l-bis(4-fluorophenyl)-A-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3- yl)methanimine (3b)

[0945] The compound 3b was obtained as a pale-yellow solid in 66% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (100 : 1).

[0946] 'H NMR (300 MHz, Chloroform-; / ) 5 7.69 - 7.61 (m, 2H), 7.45 (m, 2H), 7.40 - 7.29 (m, 3H), 7.13 - 7.02 (m, 2H), 7.01 - 6.92 (m, 2H), 6.82 - 6.74 (m, 2H), 4.26 (d, J= 7.34 Hz, 2H), 3.84 (d, J = 7.35 Hz, 2H).

[0947] 19F NMR (282 MHz, Chloroform-; / ) 584.7 - 82.3 (m, IF), 52.6 (d, = 154.83 Hz, 4F), -109.7(s, IF), -110.4(s, IF).

[0948] 13C NMR (75 MHz, Chloroform-; / ) 5 166.0, 165.4 (d, J= 117.6 Hz), 162.1 (d, J= 116.3 Hz), 144.9, 135.7 (d, J= 3.0 Hz), 132.7 (d, J= .1 Hz), 130.8 (d, J= 8.7 Hz), 129.9 (d, J= 8.2 Hz), 128.8, 127.4, 125.1, 115.5 (d, J= 21.6 Hz), 115.2 (d, J= 21.7 Hz), 68.8 - 68.5 (m), 60.2.

[0949] HRMS (ESI) calculated for C22H18F7N2S: 475.1073 [M+H]+, Found: 475.1073. l,l-bis(4-bromophenyl)-7V-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3- yl)methanimine (3c)

[0950] The compound 3c was obtained as a pale-yellow solid in 52% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (100 : 1).

[0951] 'H NMR (300 MHz, Chloroform-; / ) 5 7.49 (s, 4H), 7.46 - 7.31 (m, 5H), 7.34 - 7.22 (m, 2H),

[0952] 6.64 (d, J= 8.44 Hz, 2H), 4.26 (d, J= 7.44 Hz, 2H), 3.86 (d, J= 7.46 Hz, 2H).

[0953] 19F NMR (282 MHz, Chloroform-^ 5 88.3 - 78.5 (m, IF), 52.7 (d, J= 154.83 Hz, 4F).

[0954] 13C NMR (75 MHz, Chloroform-; / ) 5 166.1, 144.7, 138.0, 135.3, 131.6, 131.5, 130.2, 129.4, 128.8, 127.5, 125.7, 125.1, 123.9, 68.7 - 68.5 (m), 60.3.

[0955] HRMS (ESI) calculated for C22Hi8Br2F5N2S: 594.9472 [M+H]+, Found: 594.9467. l,l-bis(4-chlorophenyl)-7V-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3- yl)methanimine (3d)

[0956] The compound 3d was obtained as a pale-yellow solid in 59% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (100 : 1).

[0957] 'H NMR (300 MHz, Chloroform-; / ) 5 7.60 - 7.53 (m, 2H), 7.47 - 7.40 (m, 2H), 7.38 - 7.28 (m, 5H), 7.26 - 7.21 (m, 2H), 6.75 - 6.66 (m, 2H), 4.25 (d, J= 7.30 Hz, 2H), 3.85 (d, J= 7.34 Hz, 2H).

[0958] 19F NMR (282 MHz, Chloroform-; / ) 5 84.7 - 82.1 (m, IF), 52.6 (d, J= 154.86 Hz, 4F).

[0959] 13C NMR (75 MHz, Chloroform-; / ) 5 165.9, 144.7, 137.6, 137.2, 135.6, 134.9, 130.0, 129.2, 128.8, 128.7, 128.5, 127.5, 125.1, 68.7 - 68.5 (m), 60.3.

[0960] HRMS (ESI) calculated for C22H17CI2F5N2S: 507.0482 [M+H]+, Found: 507.0485.

[0961] N-( l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l,l-di-p-tolylmethanimine (3e)

[0962] The compound 3e was obtained as a white solid in 71% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (100 : 1).

[0963] 'H NMR (300 MHz, Chloroform-; / ) 5 7.62 - 7.46 (m, 4H), 7.44 - 7.27 (m, 3H), 7.18 (d, J = 8.00 Hz, 2H), 7.04 (d, J = 7.81 Hz, 2H), 6.69 (d, J= 8.06 Hz, 2H), 4.27 (d, J = 7.58 Hz, 2H), 3.82 (d, J= 7.63 Hz, 2H), 2.40 (s, 3H), 2.35 (s, 3H).

[0964] 19F NMR (282 MHz, Chloroform-; / ) 5 85.3 - 82.2 (m, IF), 52.8 (d, J= 154.78 Hz, 4F).

[0965] 13C NMR (75 MHz, Chloroform-; / ) 5 168.0, 145.5, 140.8, 139.1, 137.3, 134.2, 128.8, 128.8, 128.8, 128.6, 127.9, 127.1, 125.3, 69.0 - 68.7 (m), 60.2, 21.4, 21.4.

[0966] HRMS (ESI) calculated for C24H24F5N2S: 467.1575 [M+H]+, Found: 467.1576. l,l-bis(4-methoxyphenyl)-7V-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3- yl)methanimine (3f)

[0967] The compound 3f was obtained as a white solid in 53% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (20 : 1).

[0968] 'H NMR (300 MHz, Chloroforms / ) 5 7.68 - 7.59 (m, 2H), 7.56 - 7.47 (m, 2H), 7.40 - 7.28 (m, 3H), 6.93 - 6.82 (m, 2H), 6.81 - 6.64 (m, 4H), 4.25 (d, J= 7.62 Hz, 2H), 3.96 - 3.62 (m, 3H).19F NMR (282 MHz, Chloroforms / ) 5 84.0 (p, J= 155.05, 153.86 Hz, IF), 52.8 (d, J= 154.77 Hz, 4F).

[0969] 13C NMR (75 MHz, Chloroforms / ) 5 167.2, 161.6, 160.1, 145.6, 132.9, 132.2, 130.6, 129.5, 129.3, 128.6, 127.1, 125.2, 113.5, 113.4, 69.1 - 68.9 (m), 60.2, 55.4, 55.2.

[0970] HRMS (ESI) calculated for C24H24F5N2O2S: 499.1473 [M+H]+, Found: 499.1480. l-(naphthalen-2-yl)- / V-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l-phenyl methanimine (3h)

[0971] The compound 3h was obtained as a pale yellow solid in 52% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (100 : 1).

[0972] Mixtures of isomers were isolated, E / Z = 1 / 0.85

[0973] ‘HNMR (300 MHz, Methylene Chlorides / 2) 5 8.29 - 7.61 (m, 5H), 7.58 - 7.27 (m, 10H), 7.23 - 6.70 (m, 2H), 4.43 - 4.23 (m, 2H), 3.95 - 3.72 (m, 2H).

[0974] 19F NMR (282 MHz, Methylene Chlorides / 2) 5 84.8 - 82.1 (m, IF), 53.0 - 52.0 (m, 4F).

[0975] 13C NMR (75 MHz, Methylene Chlorides 2) 6 168.1, 168.0, 145.2, 145.0, 139.7, 137.2, 137.0, 134.4, 133.2, 132.7, 132.3, 130.6, 130.2, 129.2, 128.8, 128.6, 128.6, 128.2, 128.2, 128.1, 128.0, 127.9, 127.7, 127.7, 127.6, 127.3, 127.3, 127.2, 127.1, 126.7, 126.4, 125.4, 125.3, 125.1, 124.9, 68.8 - 68.5 (m), 60.4.

[0976] HRMS (ESI) calculated for C26H22F5N2S: 489.1418 [M+H]+, Found: 489.1419.

[0977] 1 -( 4-nit rophenyl )-.\-( l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3i)

[0978] The compound 3i was obtained as a yellow solid in 44% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (20 : 1).

[0979] Mixtures of isomers were isolated, E / Z = 1 / 0.4

[0980] 'H NMR (300 MHz, Chloroform-; / ) 5 8.29 - 8.03 (m, 2H), 7.88 - 7.56 (m, 2H), 7.55 - 7.27 (m, 8H), 7.03 - 6.74 (m, 2H), 4.40 - 4.23 (m, 2H), 3.87 (d, J= 7.70 Hz, 2H).

[0981] 19F NMR (282 MHz, Chloroform-; / ) 5 94.5 - 76.5 (m, IF), 61.1 - 43.1 (m, 4F).

[0982] 13C NMR (75 MHz, Chloroform-; / ) 5 166.3, 166.2, 149.1, 148.0, 145.1, 144.4, 144.4, 143.8, 138.3, 135.8, 131.3, 129.9, 129.7, 128.9, 128.9, 128.8, 128.6, 128.5, 128.5, 127.7, 127.6, 127.5, 125.1, 123.3, 68.6 - 68.3 (m), 60.8 - 60.7 (m), 60.1 - 60.0 (m).

[0983] HRMS (ESI) calculated for C22H19F5N3O2S: 484.1113 [M+H]+, Found: 484.1116. l-(3,4-dimethylphenyl)-7V-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3j)

[0984] The compound 3j was obtained as a white solid in 68% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (100 : 1). Mixtures of isomers were isolated, E / Z = 1 / 1

[0985] XH NMR (300 MHz, Chloroform-; / ) 5 7.73 - 7.61 (m, 1H), 7.57 - 7.41 (m, 3H), 7.40 - 7.27 (m, 5H), 7.25 - 7.19 (m, 1H), 7.17 - 6.96 (m, 1H), 6.85 - 6.41 (m, 2H), 4.28 (d, J= 6.86 Hz, 2H), 3.82 (dd, J= 11.43, 7.87 Hz, 2H), 2.34 - 2.26 (m, 3H), 2.29 - 2.04 (m, 3H).

[0986] 19F NMR (282 MHz, Chloroform-; / ) 5 85.2 - 82.2 (m, IF), 53.2 - 52.2 (m, 4F).

[0987] 13C NMR (75 MHz, Chloroform-; / ) 5 168.4, 168.1, 145.5, 145.4, 140.0, 139.7, 137.8, 137.4, 137.3, 136.5, 136.4, 134.4, 130.4, 129.6, 129.4, 129.3, 129.2, 129.0, 128.9, 128.6, 128.6, 128.1, 128.1, 127.9, 127.2, 127.1, 126.7, 125.4, 125.3, 68.9 - 68.6 (m), 60.3, 60.2, 19.8, 19.8, 19.7, 19.6.

[0988] HRMS (ESI) calculated for C24H24F5N2S: 467.1575 [M+H]+, Found: 467.1579. l-(2-methoxyphenyl)-7V-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3k)

[0989] The compound 3k was obtained as a white solid in 52% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (40 : 1).

[0990] Z isomer was isolated.

[0991] 'H NMR (300 MHz, Chloroform-; / ) 5 7.74 - 7.57 (m, 2H), 7.41 - 7.17 (m, 9H), 6.88 - 6.82 (m, 1H), 6.74 - 6.65 (m, 1H), 6.42 - 6.33 (m, 1H), 4.55 (d, J= 6.67 Hz, 1H), 4.34 (d, J= 7.48 Hz, 1H), 4.05 (d, J= 6.43 Hz, 1H), 3.61 - 3.53 (m, 4H).

[0992] 19F NMR (282 MHz, Chloroform-; / ) 5 85.2 - 82.6 (m, IF), 52.6 (d, J= 154.71 Hz, 4F).

[0993] 13C NMR (75 MHz, Chloroform-; / ) 5 166.1, 155.9, 144.6, 139.2, 130.6, 130.4, 128.7, 128.3, 128.1, 127.8, 127.0, 126.3, 125.5, 120.2, 110.6, 70.0 - 69.7 (m), 66.4 - 66.1 (m), 60.2, 55.1.

[0994] HRMS (ESI) calculated for C23H22F5N2OS: 469.1368 [M+H]+, Found: 469.1369.

[0995] 7V-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l-phenyl-l-(pyridin-3- yl)methanimine (31)

[0996] The compound 3m was obtained as a pale yellow solid in 66% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (5 : 1).

[0997] Mixtures of isomers were isolated, E / Z = 1 / 0.4

[0998] XH NMR (300 MHz, Chloroform-; / ) 5 8.86 - 8.01 (m, 3H), 7.70 - 7.27 (m, 9H), 7.24 - 6.77 (m, 2H), 4.37 - 4.22 (m, 2H), 3.92 - 3.81 (m, 2H).

[0999] 19F NMR (282 MHz, Chloroform-; / ) 5 84.9 - 81.5 (m, IF), 53.3 - 51.9 (m, 4F).

[1000] 13C NMR (75 MHz, Chloroform-; / ) 5 166.0, 165.6, 151.3, 150.3, 148.3, 144.7, 144.7, 138.9, 135.9, 135.8, 135.3, 135.1, 132.9, 131.1, 129.7, 128.8, 128.8, 128.6, 128.6, 128.4, 127.7, 127.6, 127.4, 125.2, 125.2, 123.1, 123.0, 68.8 - 68.4 (m), 60.5.

[1001] HRMS (ESI) calculated for C21H19F5N3S: 440.1214 [M+H]+, Found: 440.1219. l-(4-bromophenyl)-A-(l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3m)

[1002] The compound 3m was obtained as a pale-yellow solid in 56% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (100 : 1). Mixtures of isomers were isolated, E / Z = 1 / 0.6

[1003] 'H NMR (300 MHz, Chloroform-; / ) 5 7.68 - 7.46 (m, 3H), 7.51 - 7.27 (m, 7H), 7.32 - 7.19 (m, 2H), 6.88 - 6.60 (m, 2H), 4.41 - 4.08 (m, 2H), 4.02 - 3.69 (m, 2H).

[1004] 19F NMR (282 MHz, Chloroform-; / ) 5 89.6 - 76.2 (m, IF), 59.1 - 31.6 (m, 4F).

[1005] 13C NMR (75 MHz, Chloroform-; / ) 5 167.0, 144.9, 144.9, 139.2, 138.5, 136.4, 135.9, 131.5, 131.3, 130.9, 130.3, 129.5, 129.4, 128.8, 128.7, 128.3, 128.3, 127.7, 127.4, 127.3, 125.4, 125.2, 123.6, 68.9 - 68.4 (m), 60.4 - 60.1 (m).

[1006] HRMS (ESI) calculated for C22Hi9BrF5N2S: 517.0367 [M+H]+, Found: 517.0372.

[1007] 2-(4-((4-chlorophenyl)((l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3- yl)imino)methyl)phenoxy)-2-methylpropanoate (3n)

[1008] The compound 3n was obtained as a colorless oil in 48% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (40 : 1).

[1009] Mixtures of isomers were isolated, E / Z = 1 / 1

[1010] XH NMR (300 MHz, Chloroform-; / ) 5 8.10 - 7.71 (m, 4H), 7.70 - 7.58 (m, 4H), 7.55 - 7.47 (m, 1H), 7.22 - 6.95 (m, 4H), 5.46 - 5.27 (m, 1H), 4.63 - 4.42 (m, 2H), 4.13 (d, J= 7.03 Hz, 2H), 1.92 (s, 3H), 1.91 (s, 3H), 1.53 (d, J= 6.28 Hz, 3H), 1.50 (d, J= 6.28 Hz, 3H).

[1011] 19F NMR (282 MHz, Chloroform-; / ) 5 84.9 - 82.5 (m, IF), 52.7 (d, J= 154.78 Hz, 4F).

[1012] 13C NMR (75 MHz, Chloroform-; / ) 5 173.3, 173.3, 166.6, 166.3, 158.0, 156.5, 145.1, 145.0,

[1013] 138.4, 136.8, 135.5, 135.2, 132.6, 131.2, 130.2, 129.9, 129.4, 129.3, 129.1, 128.7, 128.7, 128.4, 128.3, 127.3, 127.3, 125.2, 125.1, 117.8, 117.7, 79.2, 79.2, 69.2, 60.4, 60.0, 25.3, 25.3, 21.6,

[1014] 21.5.

[1015] HRMS (ESI) calculated for C29H31CIF5N2O3S: 617.1659 [M+H]+, Found: 617.1660.

[1016] 7V-(l-(pentafluoro-k6-sulfaneyl)-3-(p-tolyl)azetidin-3-yl)-l,l-diphenylmethanimine (3al)

[1017] The compound 3al was obtained as a white solid in 67% yield following the general procedure GP7 after column chromatography on silica gel with pentane / EtOAc (100 : 1).

[1018] 'H NMR (300 MHz, Chloroform-; / ) 5 7.64 - 7.55 (m, 2H), 7.39 - 7.24 (m, 6H), 7.20 - 7.13 (m, 2H), 7.09 - 7.02 (m, 2H), 6.79 - 6.71 (m, 2H), 4.18 (d, J= 6.92 Hz, 2H), 3.71 (d, J= 7.00 Hz, 2H), 2.28 (s, 3H).

[1019] 19F NMR (282 MHz, Chloroform-; / ) 5 85.4 - 82.5 (m, IF), 52.7 (d, J= 154.81 Hz, 4F).

[1020] 13C NMR (75 MHz, Chloroform-; / ) 5 167.8, 142.2, 139.7, 137.1, 136.8, 130.5, 129.3, 129.2, 128.8, 128.2, 128.1, 127.9, 125.1, 68.9 - 68.6 (m), 60.2, 21.1.

[1021] HRMS (ESI) calculated for C23H22F5N2S: 453.1418 [M+H]+, Found: 453.1420.

[1022] 7V-2-methyl-l-(pentafluoro-k6-sulfaneyl)-3-phenylazetidin-3-yl)-l,l- diphenylmethanimine (3a4)

[1023] The compound 3a4 (cis) was obtained as a white solid in 42% yield following the general procedure after column chromatography on silica gel with pentane / EtOAc (100 : 1).

[1024] CA-isomer was isolated.

[1025] 'H NMR (300 MHz, Methylene Chloride-fife) 5 7.81 - 7.61 (m, 2H), 7.52 - 7.29 (m, 9H), 7.28 - 7.19 (m, 2H), 6.79 - 6.63 (m, 2H), 4.70 (q, J= 6.16 Hz, 1H), 3.94 (d, J= 8.24 Hz, 1H), 3.46 (d, J= 7.83 Hz, 1H), 0.98 (d, J= 6.17 Hz, 3H).

[1026] 19F NMR (282 MHz, Methylene Chloride-fife) 5 86.3 - 83.5 (m, IF), 55.2 (d, J= 153.93 Hz, 4F).13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 167.6, 141.9, 139.7, 137.2, 130.5, 129.0, 128.7, 128.2, 128.0, 128.0, 128.0, 127.1, 126.7, 76.2 - 76.1 (m), 64.6 - 64.4 (m), 63.4, 54.2, 16.0. HRMS (ESI) calculated for C23H22F5N2S: 453.1418 [M+H]+, Found: 453.1422.

[1027] 2.4. Bicyclobutanyl series

[1028] General procedure (GP8):

[1029] To a 10 mL tube were sequentially added the bicyclobutanyl compound (0.15 mmol, 1.5 equiv.), the compound of formula (I) (0.1 mmol, 1.0 equiv.), 9H-thioxanthen-9-one (0.005 mmol, 5 mol%) and anhydrous ethyl acetate (1 mL, 1 M) under argon atmosphere. The reaction mixture was stirred at room temperature under the irradiation of 405 nm blue light overnight. After completion, the reaction was quenched by saturated brine, then extracted with ethyl acetate (3x 10 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material obtained was then purified by column chromatography on silica gel.

[1030] Methyl 3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-l-carboxylate (6a)

[1031] The compound 6a was obtained as a colorless oil in 75% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1032] The ratio of synlanti = 0.83 / 1

[1033] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.83 - 7.44 (m, 3H), 7.45 - 7.11 (m, 9H), 7.07 - 6.50 (m, 3H), 3.94 - 2.87 (m, 7H).

[1034] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 87.7 - 76.8 (m, IF), 51.0 (d, J= 143.80 Hz, 4F).

[1035] 13C NMR (76 MHz, Methylene Chloride-6 / 2) 5 146.1, 143.3, 140.5, 140.1, 137.7, 137.3, 132.3, 130.3, 130.2, 129.9, 128.8, 128.6, 128.3, 128.3, 128.3, 128.2, 128.1, 128.0, 128.0, 127.9, 127.9, 127.7, 127.6, 127.0, 126.7, 126.5, 125.3, 53.5, 53.1, 47.7, 47.5.

[1036] HRMS (ESI) calculated for C25H23F5NO2S: 496.1364 [M+H]+, Found: 496.1366. Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-l-carboxylate (6c anti)

[1037] The compound 6c (anti) was obtained as a colorless oil in 41% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1038] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.66 - 7.53 (m, 1H), 7.48 - 7.34 (m, 4H), 7.29

[1039] - 7.23 (m, 2H), 7.18 - 7.11 (m, 2H), 6.91 - 6.84 (m, 2H), 6.51 - 6.40 (m, 2H), 3.81 (s, 3H),

[1040] 3.45 (s, 4H).

[1041] 19F NMR (282 MHz, Methylene Chloride-tfc) 5 87.7 - 76.5 (m, IF), 51.0 (d, J= 143.75 Hz, 4F).

[1042] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 168.1, 145.5, 138.9, 135.7, 131.4, 131.2, 131.1,

[1043] 129.8, 129.2, 128.4, 126.7, 125.3, 122.5, 53.6.

[1044] HRMS (ESI) calculated for C25H2oBr2F5N02S: 651.9574 [M+H]+, Found: 651.9578.

[1045] Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-l-carboxylate (6c syn)

[1046] The compound 6c syn was obtained as a colorless oil in 36% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1047] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.68 - 7.39 (m, 6H), 7.33 - 7.04 (m, 5H), 6.66

[1048] - 6.56 (m, 2H), 3.48 - 3.28 (m, 7H).

[1049] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 86.9 - 75.2 (m, IF), 51.0 (d, J= 143.96 Hz, 4F).13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 164.8, 142.9, 138.5, 136.0, 131.4, 131.2, 129.8, 128.2, 127.2, 126.5, 125.1, 123.0, 60.3, 53.2.

[1050] HRMS (ESI) calculated for C25H2oBr2F5N02S: 651.9574 [M+H]+, Found: 651.9569.

[1051] Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-l-carboxylate (6d anti)

[1052] The compound 6d (anti) was obtained as a colorless oil in 35% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1053] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.51 - 7.40 (m, 2H), 7.33 - 7.27 (m, 2H), 7.22 - 7.07 (m, 5H), 6.97 - 6.83 (m, 2H), 6.63 - 6.38 (m, 2H), 3.82 (s, 3H), 3.46 (s, 4H).

[1054] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 89.0 - 75.8 (m, IF), 51.0 (d, J= 143.74 Hz, 4F).

[1055] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 168.0, 145.6, 138.5, 136.7, 135.4, 134.2, 129.6, 129.0, 128.7, 128.4, 128.2, 128.1, 126.7, 125.3, 61.9, 47.6.

[1056] HRMS (ESI) calculated for C25H21CI2F5NO2S: 564.0585 [M+H]+, Found: 564.0587.

[1057] Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-l-carboxylate (6d syn)

[1058] The compound 6d syn was obtained as a colorless oil in 30% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1). H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.77 - 7.68 (m, 1H), 7.56 - 7.45 (m, 3H), 7.35 - 7.27 (m, 3H), 7.25 - 7.19 (m, 2H), 7.15 - 7.04 (m, 2H), 6.72 - 6.61 (m, 2H), 3.50 - 3.24 (m, 7H).

[1059] 19F NMR (282 MHz, Methylene Chloride-tfc) 5 83.0 - 80.4 (m, IF), 51.0 (d, J= 143.98 Hz, 4F).

[1060] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 164.7, 143.0, 138.1, 136.6, 135.6, 134.8, 131.3, 129.6, 129.3, 128.7, 128.4, 128.2, 127.2, 126.5, 60.3, 53.2, 47.5.

[1061] HRMS (ESI) calculated for C25H21CI2F5NO2S: 564.0585 [M+H]+, Found: 564.0586.

[1062] Methyl-3-((di-p-tolylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-l-carboxylate (6e)

[1063] The compound 6e was obtained as a colorless oil in 48% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1064] The ratio of synlanti = 0.73 / 1

[1065] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.71 - 7.05 (m, 9H), 7.01 - 6.43 (m, 4H), 3.88 - 3.19 (m, 7H), 2.49 - 2.23 (m, 6H).

[1066] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 83.6 - 80.5 (m,lF), 51.6 - 49.9 (m, 4F).

[1067] 13C NMR (75 MHz, Methylene Chloride-d2) 5 170.5, 168.0, 167.5, 166.4, 146.5, 143.6, 140.7, 140.5, 138.6, 138.2, 137.6, 134.8, 134.5, 130.0, 128.8, 128.6, 128.5, 128.3, 128.3, 128.3, 128.2, 128.0, 127.9, 127.7, 126.9, 126.7, 126.4, 125.3, 61.6, 60.3, 53.5, 53.1, 47.6, 47.6, 47.6, 47.5, 21.1, 21.0, 21.0, 21.0.

[1068] HRMS (ESI) calculated for C27H27F5NO2S: 524.1677 [M+H]+, Found: 524.1679.

[1069] Methyl-3-((bis(4-methoxyphenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-l-carboxylate (6f)

[1070] The compound 6f was obtained as a colorless oil in 69% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (15: 1).

[1071] The ratio of synlanti = 1 / 1

[1072] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.81 - 7.43 (m, 2H), 7.28 - 7.10 (m, 4H), 7.05 - 6.80 (m, 4H), 6.74 - 6.48 (m, 3H), 3.91 - 3.79 (m, 7H), 3.50 - 3.26 (m, 6H).

[1073] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 83.6 - 80.4 (m, IF), 52.1 - 49.3 (m, 4F).

[1074] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 169.7, 165.7, 161.6, 161.4, 159.8, 159.5, 146.7, 143.8, 133.8, 133.2, 130.1, 130.0, 130.0, 129.7, 129.4, 129.3, 128.3, 128.0, 126.9, 126.6, 126.4, 125.3, 113.3, 113.1, 113.1, 85.8 - 85.2 (m), 84.0 - 83.4 (m), 55.3, 55.3, 55.2, 55.2, 53.5, 53.1. HRMS (ESI) calculated for C27H27F5NO4S: 556.1575 [M+H]+, Found: 556.1578.

[1075] Methyl-3-(((2-methoxyphenyl)(phenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane-l-carboxylate (6k)

[1076] The compound 6k was obtained as a colorless oil in 60% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1077] The ratio of synlanti = 1 / 0.9

[1078] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.64 - 7.45 (m, 2H), 7.47 - 6.95 (m, 8H), 6.94 - 6.84 (m, 1H), 6.82 - 6.37 (m, 3H), 3.85 (s, 2H), 3.62 - 3.45 (m, 4H), 3.42 - 3.06 (m, 4H).

[1079] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 83.9 - 80.2 (m, IF), 51.8 - 50.0 (m, 4F).

[1080] 13C NMR (75 MHz, Methylene Chloride-6 / 2) 5 168.0, 167.4, 167.4, 164.2, 155.8, 155.3, 144.8, 142.5, 140.1, 139.6, 130.3, 130.1, 130.0, 129.6, 129.2, 128.5, 127.9, 127.9, 127.8, 127.6, 127.5, 127.0, 126.9, 126.7, 126.2, 126.0, 125.5, 120.1, 119.7, 110.5, 110.0, 61.7, 60.3, 54.9, 54.5, 49.2 - 49.1 (m), 48.0, 47.5, 44.4. HRMS (ESI) calculated for C26H25F5NO3S: 526.1470 [M+H]+, Found: 526.1470.

[1081] Methyl-3-((diphenylmethylene)amino)-3-(3-fluorophenyl)-l-(pentafluoro-k6- sulfaneyl)cyclobutane-l-carboxylate (6al)

[1082] The compound 6al was obtained as a colorless oil in 66% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1083] The ratio of synlanti = 1 / 1

[1084] 'H NMR (300 MHz, Methylene Chloride-6 / 2) 5 7.82 - 7.50 (m, 2H), 7.46 - 6.94 (m, 7H), 6.95 - 6.69 (m, 3H), 6.66 - 6.21 (m, 2H), 4.23 - 2.56 (m, 7H).

[1085] 19F NMR (282 MHz, Methylene Chloride-tfc) 5 89.0 - 77.1 (m, IF), 54.2 - 43.6 (m, 4F), -110.4 - -119.2 (m, IF).

[1086] 13C NMR (75 MHz, Methylene Chloride-tfc) 5 170.7, 167.9, 167.4, 162.6 (d, J = 243.7 Hz), 162.5 (d, J= 243.7 Hz), 148.5, 148.4, 146.2, 146.0, 140.2, 140.0, 137.6, 137.3, 130.5 (d, J = 8.2 Hz), 129.9 (d, J= 8.2 Hz), 129.6 (d, J= 8.2 Hz), 128.7, 128.4, 128.3, 128.2, 128.1, 127.9, 127.8, 127.8, 127.5, 122.3, 122.2, 121.1, 121.1, 113.9 (d, J= 21.1 Hz), 113.8 (d, J= 21.1 Hz), 113.3 (d, J= 21.1 Hz), 112.5 (d, J= 21.1 Hz), 85.4 - 84.7 (m), 83.6 - 82.8 (m), 61.3, 60.0, 53.6, 53.2, 47.7, 47.6.

[1087] HRMS (ESI) calculated for C25H22F6NO2S: 514.1270 [M+H]+, Found: 514.1272.

[1088] Methyl-3-(4-chlorophenyl)-3-((diphenylmethylene)amino)-l-(pentafluoro-k6- sulfaneyl)cyclobutane-l-carboxylate (6a2)

[1089] The compound 6a2 was obtained as a colorless oil in 73% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1090] The ratio of synlanti = 0.9 / 1 'H NMR (300 MHz, Methylene Chloride-tfc) 5 7.84 - 6.95 (m, 11H), 6.90 - 6.69 (m, 2H), 6.63 - 6.47 (m, 1H), 3.92 - 3.11 (m, 7H).

[1091] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 85.6 - 76.8 (m, IF), 51.8 - 49.3 (m, 4F).

[1092] 13C NMR (75 MHZ, Methylene Chloride-6 / 2) 5 170.5, 167.9, 167.4, 167.2, 144.6, 142.0, 140.3, 139.8, 137.6, 137.4, 132.7, 132.2, 130.5, 130.4, 128.7, 128.3, 128.3, 128.3, 128.2, 128.2, 128.1, 128.1, 127.9, 127.9, 127.8, 127.8, 127.5, 126.8, 85.4 - 84.7 (m), 83.6 - 82.9 (m), 61.2, 59.9,

[1093] 53.6, 53.3, 47.7, 47.5.

[1094] HRMS (ESI) calculated for C25H22CIF5NO2S: 530.0974 [M+H]+, Found: 530.0976.

[1095] Methyl-3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-(4- (trifluoromethyl)phenyl)cyclobutane-l-carboxylate (6a3)

[1096] The compound 6a3 was obtained as a colorless oil in 75% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1097] The ratio of synlanti = 1 / 1

[1098] ‘HNMR (300 MHz, Methylene Chloride-tfc) 5 7.85 - 7.21 (m, 10H), 7.16 - 7.08 (m, 1H), 7.05 - 6.97 (m, 1H), 6.87 - 6.68 (m, 1H), 6.62 - 6.53 (m, 1H), 3.89 - 3.19 (m, 7H).

[1099] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 82.8 - 80.3 (m, IF), 52.2 - 49.6 (m, 4F), -62.8 - -63.0 (m, 3F).

[1100] 13C NMR (75 MHZ, Methylene Chloride-6 / 2) 5 170.7, 167.8, 167.4, 149.7, 147.6, 140.1, 139.7,

[1101] 137.6, 137.4, 130.6, 130.5, 129.9, 128.8, 128.4, 128.3, 128.2, 128.2, 128.1, 128.0, 127.9, 127.6, 127.3, 127.1, 125.8, 125.3 - 124.9 (m), 85.5 - 84.7 (m), 124.1 (q, J= 271.21 Hz), 83.5 - 82.8 (m), 61.4, 60.1, 53.6, 53.3, 47.6, 47.4.

[1102] HRMS (ESI) calculated for C26H22F8NO2S: 564.1238 [M+H]+, Found: 564.1235.

[1103] Methyl-3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-(3-

[1104] (trifluoromethyl)phenyl)cyclobutane-l-carboxylate (6a4)

[1105] The compound 6a4 was obtained as a colorless oil in 76% yield following the general procedure GP8 after column chromatography on silica gel with pentane / EtOAc (50: 1).

[1106] The ratio of synlanti = 0.6 / 1 'H NMR (300 MHz, Methylene Chloride-tfc) 5 7.84 - 7.07 (m, 12H), 7.04 - 6.46 (m, 2H), 3.95 - 3.26 (m, 7H).

[1107] 19F NMR (282 MHz, Methylene Chloride-6 / 2) 5 82.8 - 80.1 (m, IF), 51.7 - 50.1 (m, 4F), -62.7 - -63.0 (m, 3F).

[1108] 13C NMR (75 MHZ, Methylene Chloride-6 / 2) 5 170.8, 168.1, 167.8, 167.3, 146.7, 144.4, 140.0, 139.7, 137.6, 137.3, 132.3, 131.1, 130.6, 130.5, 129.9, 129.1 - 129.0 (m), 129.0, 129.0, 128.8,

[1109] 128.4, 128.3, 128.2, 128.1, 128.0, 127.9, 127.5, 127.3, 125.8 (q, J = 4.2 Hz), 123.8 (q, 3.7

[1110] Hz), 123.3 (q, J= 3.8 Hz), 122.8 (q, J= 3.9 Hz), 122.2 (q, J= 4.7 Hz), 122.1 (q, J = 3.9 Hz), 85.5 - 84.6 (m), 83.5 - 82.6 (m), 61.4, 60.0, 53.6, 53.2, 47.7, 47.5.

[1111] HRMS (ESI) calculated for C26H22F8NO2S: 564.1238 [M+H]+, Found: 564.1234.

Claims

CLAIMS1. A process for preparing a compound of formula (I):wherein: Ri and R2 represent independently a radical selected in a group consisting of:• a hydrogen,• a radical selected in a group consisting of a (Ci-Ce)alkyl, and a 5-14 membered ring, said radical is optionally substituted by at least one radical selected in a group consisting of: a halogen,- a (Ci-Ce)alkyl, a (Ci-Ce)alkyloxy, a nitro,- a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), and• a CO-O-Ra or a CO-Rb with Ra and Rb represent independently a radical selected in a group consisting of: a (Ci-Ci2)alkyl optionally substituted by a (C2-Ci2)alkynyl or by a 5- 14 membered ring optionally substituted by a (Ci-Ce)alkyl, and and a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl; or Ri and R2 may form together a 5-14 membered ring optionally substituted by a radical selected in a group consisting of:• a halogen,• a (Ci-Ce)alkyl,• a (Ci-Ce)alkyloxy,• a nitro,• a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and• a (Ci-Ce)alkyl-CO-O-(5-14 membered ring),with the proviso that when one of Ri and R2 is a hydrogen, then the other is not a hydrogen; and the stereoisomers, and the salts thereof; comprising the following steps of: a) reacting pentafluorosulfanyldichloramine (SF5NCI2) with a compound of formula (I’):with Y represents N2 or O, andRi and R2 are such as above defined; and b) recovering said compound of formula (I).

2. A compound of formula (I):with Ri and R2 are such as defined in claim 1, obtained by the process according to claim 1.

3. A compound of formula (I)wherein: Ri and R2 represent independently a radical selected in a group consisting of:• a hydrogen,• a radical selected in a group consisting of a (Ci-Ce)alkyl, and a 5-14 membered ring, said radical is optionally substituted by at least one radical selected in a group consisting of: a halogen, a (Ci-Ce)alkyl, a (Ci-Ce)alkyloxy,a nitro,- a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), and• a CO-O-Ra or a CO-Rb with Ra and Rb represent independently a radical selected in a group consisting of: a (Ci-Ci2)alkyl optionally substituted by a (C2-Ci2)alkynyl or by a 5- 14 membered ring optionally substituted by a (Ci-Ce)alkyl, and and a 5-14 membered ring optionally substituted by a (Ci-C24)alkyl; or Ri and R2, may form together a 5-14 membered ring optionally substituted by a radical selected in a group consisting of:• a halogen,• a (Ci-Ce)alkyl,• a (Ci-Ce)alkyloxy,• a nitro,• a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, and• a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), with the proviso that when one of Ri and R2 is a hydrogen, then the other is not a hydrogen; and the stereoisomers, and the salts thereof.

4. The process according to claim 1 or the compound according to claim 2 or 3, wherein Ri represents a phenyl optionally substituted by a radical selected in a group consisting of a bromine, a chorine, a fluorine, a methyl, a methoxy, a nitro, a CO-O-methyl.

5. The process according to claim 1 or 4 or the compound according to any one of claims 2 to 4, wherein R2 represents a 5-14 membered ring, preferably selected in a group consisting of an aryl and a heteroaryl, said 5-14 membered ring being optionally substituted by at least one radical selected in a group consisting of:- a halogen, preferably a fluorine, a bromine, or a chlorine,- a (Ci-Ce)alkyl, preferably a methyl,- a (Ci-Ce)alkyloxy, preferably a methoxy,- a O-(Ci-C6)alkyl-CO-O-(Ci-C6)alkyl, preferably a O-C(CH3)2-CO-O-CH(CH3)2, and- a (Ci-Ce)alkyl-CO-O-(5-14 membered ring), preferably a CH(CH3)-CO-O- (adamantanyl).

6. The process according to any one of claims 1 and 4 to 5 or the compound according to any one of claims 2 to 5, wherein R2 represents a CO-O-Ra or a CO-Rb, preferably a CO-O-Ra, with Ra and Rb represent independently a radical selected in a group consisting of:- a (Ci-Ci2)alkyl optionally substituted by a radical selected by a (C2-Ci2)alkynyl, and a 5-14 membered ring optionally substituted by a (Ci-Ce)alkyl, and- a 5-14 membered ring optionally substituted by a radical selected in a group consisting of a (Ci-C24)alkyl.

7. The process according to any one of claims 1 and 4 to 6 or the compound according to any one of claims 2 to 6, wherein Rarepresents a radical selected in a group consisting of a methyl, an ethyl, an hexyl, an isobutyl, a 2-methylbutyl, a 2-methylbut-3-yn-2yl, a tetrahydrofuranyl, a cyclohexyl, a 2-isopropyl-5-methylcyclohexyl, a 2-6,6-dimethylbicyclo[3.1.1]hept-2-en-2- yl)ethyl, an adamantanyl, a 2,2,7,7-tetramethyltetrahydro-5H-bis([l,3]dioxole)[4,5-b:4’,5’- d]pyran-5-yl)methyl, a phenyl, and a tetramethyl-2-(4,8,12-trimethyltridecyl)-chroman-6-yl.

8. The process according to claim 1 or the compound according to claim 2 or 3, wherein said compound is selected in a group consisting of:- N-(pentafluoro-Z6-sulfaneyl)-l,l-diphenylmethanimine (2a);- l,l-Bis(4-fluorophenyl)-N-(pentafluoro-Z6-sulfaneyl)methanimine (2b);- l,l-Bis(4-bromophenyl)-N-(pentafluoro-Z6-sulfaneyl)methanimine (2c);- l , l -Bis(4-chlorophenyl)-N-(pentafluoro-k6-sulfaneyl)methanimine (2d);- N-(pentafluoro-A6-sulfaneyl)- l , l -di-p-tolylmethanimine (2e);- 1,1 -Bis(4-methoxyphenyl)-N-(pentafluoro-Z6-sulfaneyl)methanimine (2f);- N-(pentafluoro-k6-sulfaneyl)-9H-fluoren-9-imine (2g);- (Z)-l -(naphthal en-2-yl )-N-(pentafluoro-k6-sulfaneyl )- l -phenyl methani mine (2h);- (E)- 1 -(4-nitrophenyl)-N-(pentafluoro-Z6-sulfaneyl)- 1 -phenylmethanimine (2i);- (E)-l -(3, 4-dimethylphenyl)-N-(pentafluoro-Z6-sulfaneyl)-l -phenylmethanimine (2j);- (E)-l-(2-methoxyphenyl)-N-(pentafluoro-Z6-sulfaneyl)-l -phenylmethanimine (2k);- (Z)-N-(pentafluoro-Z6-sulfaneyl)-l -phenyl- l-(pyri din-3 -yl)methanimine (21);- (E)- 1 -(4-bromophenyl)-N-(pentafluoro-Z6-sulfaneyl)- 1 -phenylmethanimine (2m);- Isopropyl (E)-2-(4-((4-chlorophenyl)((pentafluoro-X6-sulfaneyl)imino)methyl)phenoxy)-2- methylpropanoate (2n);(lR,3S,5r,7r)-Adamantan-2-yl 2-(3-((Z)-((pentafluoro-X6- sulfaneyl)imino)(phenyl)methyl)phenyl)propanoate (2o);- Ethyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2p);- Ethyl (Z)-2-(4-bromophenyl)-2-((pentafluoro-X6-sulfaneyl)imino)acetate (2q);- Ethyl (Z)-2-(4-nitrophenyl)-2-((pentafluoro-X6-sulfaneyl)imino)acetate (2r);- Methyl (Z)-4-(2-methoxy-2-oxo-l-((pentafluoro-X6-sulfaneyl)imino)ethyl)benzoate (2s);- Ethyl (Z)-2-(4-methoxyphenyl)-2-((pentafluoro-X6-sulfaneyl)imino)acetate (2t);- Ethyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-(o-tolyl)acetate (2u);- Hexyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2v);- Isobutyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2w);- (S)-2-Methylbutyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2x);- 2-Methylbut-3-yn-2-yl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2y);- Tetrahydrofuran-3-yl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2z);- Cyclohexyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2aa);(2R,5S)-2-Isopropyl-5-methylcyclohexyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2- phenylacetate (2ab);2-((lR,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl (Z)-2-((pentafluoro-X6- sulfaneyl)imino)-2-phenylacetate (2ac);- (lr,3r,5r,7r)-Adamantan-2-yl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2ad);((3aS,5S,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2ae);- Phenyl (Z)-2-((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2af);(S)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl (Z)-2- ((pentafluoro-X6-sulfaneyl)imino)-2-phenylacetate (2ag); and- (Z)-2-((pentafluoro-X6-sulfaneyl)imino)- 1 ,2-Diphenylethan- 1 -one (2ah).

9. Use of a compound of formula (I) as defined in any one of claims 2 to 8 for preparing a molecule comprising a pentafluorosulfanyl (SFs) group or for incorporating a pentafluorosulfanyl (SFs) group in a molecule.

10. A process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of:al) reacting a compound of formula (I) as defined in any one of claims 2 to 8 with a molecule comprising a styrene unit in presence of thioxanthone (TXO) under blue LED irradiation; and bl) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

11. A molecule selected in a group consisting of:- N-(2-(pentafluoro-X6-sulfaneyl)-l-(p-tolyl)ethyl)-l, 1-diphenylmethanimine (4a);- N-(2-(pentafluoro-X6-sulfaneyl)- 1 -(m-tolyl)ethyl)- 1 , 1 -diphenylmethanimine (4b);- N-(2-(pentafluoro-X6-sulfaneyl)- 1 -(o-tolyl)ethyl)- 1 , 1 -diphenylmethanimine (4c);- N-(l-(4-(tert-butyl)phenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)-l, 1-diphenylmethanimine (4d);- 4-( l -((di phenyl methyl ene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Phenyl acetate (4e);- N-(2-(pentafluoro-X6-sulfaneyl)- 1 -phenylethyl)- 1 , 1 -diphenylmethanimine (4f);- N-( 1 -(naphthal en-2-yl )-2-(pentafl uoro-X6-sulfaneyl )ethyl )- 1 , 1 -diphenylmethanimine (4g);- N-( 1 -(4-chlorophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4h);- N-(l-(4-bromophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)-l, 1-diphenylmethanimine (4i);- N-(l-(4-iodophenyl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1,1 -diphenylmethanimine (4j);- N-( 1 -([ 1 , 1 '-biphenyl]-4-yl)-2-(pentafluoro-X6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4k);- 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Benzonitrile (41);- N-( 1 -(4-nitrophenyl)-2-(pentafluoro-k6-sulfaneyl)ethyl)- 1 , 1 -diphenylmethanimine (4m);- 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)Benzaldehyde (4n);- N-(2-(pentafluoro-X.6-sulfaneyl)- 1 , 1 -diphenylethyl)- 1 , 1 -diphenylmethanimine (4o);- N-( 1 -(pentafl uoro-k6-sulfaneyl )-2-phenyl propan-2-yl )- 1 , 1 -diphenylmethanimine (4p);- N-(2-(pentafluoro-X6-sulfaneyl)-l-(thiophen-2-yl)ethyl)-l, 1-diphenylmethanimine (4q);(1 S,2R,5S)-2-isopropyl-5-methylcyclohexyl 4-(l-((diphenylmethylene)amino)-2- (pentafluoro-k6-sulfaneyl)ethyl)benzoate (4r);((S)-4-(prop- 1 -en-2-yl)cyclohex- 1 -en- 1 -yl)Methyl 4-( 1 -((diphenylmethylene)amino)-2-(pentafluoro-k6-sulfaneyl)ethyl)benzoate (4s);((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-k6- sulfaneyl)ethyl)benzoate (4t);2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-A6-sulfaneyl)ethyl)benzoate (4u);(S)-3,7-dimethyloct-6-en-l-yl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X.6- sulfaneyl)ethyl)Benzoate (4v);4-Formyl-2-methoxyphenyl 4-( l -((di phenyl methylene)amino)-2-(pentafluoro-A6-sulfaneyl)ethyl)benzoate (4w);(8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,ll,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(l-((diphenylmethylene)amino)-2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (4x); and(R)-2, 5 ,7, 8-Tetramethy l-2-((4R, 8R)-4, 8, 12-trimethyltridecyl)chroman-6-yl 4-( 1 -((diphenylmethylene)amino)-2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (4y).

12. A process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a2) reacting a compound of formula (I) as defined in any one of claims 2 to 8 with a molecule comprising a styrene unit in presence of diethyl 2,6-dimethyl-l,4-dihydropyridine-3,5- dicarboxylate, [Ir(dF(CF3)ppy)2dtbbpy]PFe, and chlorohydric acid, under blue LED irradiation; and b2) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

13. A molecule selected in a group consisting of:- (4-(tert-butyl)phenethyl)Pentafluoro-X6-sulfane (5b);- (4-(chloromethyl)phenethyl)Pentafluoro-X6-sulfane (5e);- Pentafhioro(4-iodophenethyl)- X6-sulfane (5h);- (2-([l,l'-biphenyl]-4-yl)ethyl)Pentafluoro-X6-sulfane (5j);- (1 S,2R,5S)-2-Isopropyl-5-methylcyclohexyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5k);(S)-(4-(prop- 1 -en-2-yl)cyclohex- 1 -en- 1 -yl)Methyl 4-(2-(pentafluoro-X6- sulfaneyl)ethyl)benzoate (51);((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-5H-bis([l,3]dioxolo)[4,5-b:4',5'- d]pyran-5-yl)methyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5m);2-((lR,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)Ethyl 4-(2-(pentafhioro-X6- sulfaneyl)ethyl)benzoate (5n);- (S)-3,7-Dimethyloct-6-en-l-yl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5o);- 4-Formyl-2-methoxyphenyl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5p); and(8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,l l,12,13,14,15,16,17-decahydro-6H- cyclopenta[a]phenanthren-3-yl 4-(2-(pentafluoro-X6-sulfaneyl)ethyl)benzoate (5q).

14. A process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a3) reacting a compound of formula (I) as defined in any one of claims 2 to 8 with a molecule comprising an azabicyclobutanyl in presence of thioxanthone (TXO) and ethyl acetate under blue LED irradiation; and b3) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

15. A molecule selected in a group consisting of:- N-( l-(pentafluoro-X6-sulfaneyl)-3-phenylazeti din-3 -yl)- 1, 1-diphenylmethanimine (3a);- l,l-bis(4-fluorophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3b);- l,l-bis(4-bromophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3 c)- l,l-bis(4-chlorophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)methanimine (3d);- N-(l-(pentafluoro-X.6-sulfaneyl)-3 -phenylazeti din-3 -yl)-l,l-di-p-tolylmethanimine (3e); l,l-bis(4-methoxyphenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3- yl)methanimine (3f);- A-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)-9Z7-fluoren-9-imine (3g);1 -(naphthal en-2-yl)-N-(l -(pentafl uoro-X6-sulfaneyl )-3 -phenylazeti din-3 -yl)- 1 - phenylmethanimine (3h); l-(4-nitrophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3 -phenylazeti din-3 -yl)-l- phenylmethanimine (3i); l-(3,4-dimethylphenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3j);1 -(2-methoxyphenyl)-N-(l -(pentafl uoro-X6-sulfaneyl )-3 -phenylazeti din-3 -yl)- 1 - phenylmethanimine (3 k);N-(l -(pentafl uoro-k6-sulfaneyl )-3 -phenylazeti din-3 -yl)- 1 -phenyl- 1 -(pyri din-3 - yl)methanimine (31); l-(4-bromophenyl)-N-(l-(pentafluoro-X6-sulfaneyl)-3-phenylazetidin-3-yl)-l- phenylmethanimine (3 m);2-(4-((4-chlorophenyl)((l-(pentafluoro-X.6-sulfaneyl)-3-phenylazetidin-3- yl)imino)methyl)phenoxy)-2-methylpropanoate (3n);- N-( 1 -(pentafluoro-X6-sulfaneyl)-3 -(p-tolyl)azetidin-3 -yl)- 1 , 1 -diphenylmethanimine (3 a 1 );N-( 1 -(pentafluoro-X6-sulfaneyl)-3 -(4-(tri fl uorom ethyl )phenyl )azeti din-3 -yl)- 1,1- diphenylmethanimine (3a2);(3-((diphenylmethylene)amino)-l-(pentafluoro-X6-sulfaneyl)azetidin-3- yl)(phenyl)methanone (3a3); andN-2-methyl- l-(pentafluoro-X6-sulfaneyl)-3-phenylazeti din-3 -yl)-l,l-diphenylmethanimine (3a4).

16. A process for preparing a molecule comprising a pentafluorosulfanyl (SFs) group comprising the following steps of: a4) reacting a compound of formula (I) as defined in any one of claims 2 to 8 with a molecule comprising a bicyclobutanyl in presence of thioxanthone (TXO) and ethyl acetate, under blue LED irradiation; and b4) recovering said molecule comprising a pentafluorosulfanyl (SFs) group.

17. A molecule selected in a group consisting of:- Methyl 3 -((diphenylmethylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3 -phenylcyclobutane- 1- carboxylate (6a);- Methyl 3-((bis(4-fluorophenyl)methylene)amino)- l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6b);Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6c anti);Methyl-3-((bis(4-bromophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6c syn);Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane-1 -carboxylate (6d anti)Methyl-3-((bis(4-chlorophenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6d syn);- Methyl-3-((di-p-tolylmethylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3-phenylcyclobutane- 1 -carboxylate (6e);Methyl-3-((bis(4-methoxyphenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (6f);- Methyl 3-((9Z7-fluoren-9-ylidene)amino)-l-(pentafluoro-X6-sulfaneyl)-3-phenylcyclobutane- 1 -carboxylate (6g);- Methyl (Z)-3-(((2-methoxyphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)- 3 -phenyl cy cl obutane- 1 -carb oxy 1 ate (6h) ;- Methyl 3-(((3,4-dimethylphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcy cl obutane- 1 -carboxylate (6i);Methyl 3 -(((4-bromophenyl)(phenyl)methylene)amino)- 1 -(pentafl uoro-k6-sul faneyl )-3 - phenylcyclobutane- 1 -carboxylate (6j );Methyl-3-(((2-methoxyphenyl)(phenyl)methylene)amino)-l-(pentafluoro-X6-sulfaneyl)-3- phenylcy cl obutane- 1 -carboxylate (6k);Methyl 3-(((4-nitrophenyl)(phenyl)methylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3- phenylcyclobutane- 1 -carboxylate (61);Methyl l-(pentafluoro-k6-sulfaneyl)-3-phenyl-3-((phenyl(pyridin-3- yl)methylene)amino)cy cl obutane- 1 -carboxylate (6m);Methyl-3-((diphenylmethylene)amino)-3 -(3 -fluorophenyl)- l-(pentafluoro-k6- sulfaneyl)cy cl obutane- 1 -carboxylate (6al );Methyl-3-(4-chlorophenyl)-3-((diphenylmethylene)amino)-l-(pentafluoro-X.6- sulfaneyl)cy cl obutane- 1 -carboxylate (6a2);Methyl-3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-(4-(trifluoromethyl)phenyl)cyclobutane-l -carboxylate (6a3); andMethyl-3-((diphenylmethylene)amino)-l-(pentafluoro-k6-sulfaneyl)-3-(3-(trifluoromethyl)phenyl)cyclobutane-l -carboxylate (6a4).

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