Trifluoromethylthiocopper. A reagent for the introduction of the trifluoromethylthio group into aromatic nuclei

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

“…To avoid isolation of (trifluoromethylthio)copper, the group of Remy succeeded to get aryl trifluoromethyl sulfides by reaction of aryl iodides with (trifluoromethylthio)mercury(II) in the presence of copper 57. In that case, the active copper reagent was formed in situ during the reaction .…”

An Electrophilic Hypervalent Iodine Reagent for Trifluoromethylthiolation

“…A more straightforward strategy would be the direct formation of a new CÀSCF 3 bond. [10] In recent years, several elegant methods employing transitionmetal catalysts [11] or metal-free conditions [12] have emerged for the direct trifluoromethanesulfanylation of aryl halides, boronic acids, or alkynes with a nucleophilc trifluoromethylthio reagent under mild conditions. Despite their great advantages, these reactions typically involved the formation of C sp 2 ÀSCF 3 or C sp ÀSCF 3 bonds, whereas processes that facilitate the construction of C sp 3 ÀSCF 3 bonds remain largely unexplored.…”

Recent Advances in Transition-Metal-Catalyzed Trifluoromethylation and Related Transformations

“…95 Alternatively, disulfide was employed as the source of the (trifluoromethyl)sulfanyl group, and inexpensive copper(II) acetate was used as the catalyst. The reaction showed high generality, excellent selectivity to- Within the copper-catalyzed or -mediated trifluoromethylthiolation, copper(I) trifluoromethanethiolate was proposed as the real trifluoromethylthiolation reagent, 96 and it could be isolated as a complex with a solvent, such as N,N-dimethylformamide and N-methyl-2-pyrrolidone (NMP). 97 Very recently, Weng, Huang and co-workers synthesized a series of copper(I)-(trifluoromethyl)sulfanyl complexes (10 and 11) with chelating nitrogen ligands and applied them in the efficient trifluoromethylthiolation of aryl halides (Scheme 50).…”