A New Method for the Syntheses of Aryl and Heteroaryl Trifluoromethyl Sulfides

Crystal Engineering with Symmetrical Threefold Acceptor-Substituted Triaminobenzenes

“…260 ± 275 8C (decomp) which could be recrystallized from dioxane without improvement in purity or alteration of the decomposition point. 1 [26,50] (418 mg, 1.17 mmol) in acetic acid (10 mL) and 15 % HCl (2 mL) was saturated with chlorine gas at RT. After 30 min, colorless needles separate; the solution is saturated with chlorine gas again after 3 h. After standing overnight, the solution is extracted with dichloromethane to give almost pure (TLC) 21 (502 mg, quant) containing only small amounts of the trichlorination product as judged by MS.…”

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

“…Silver(I) trifluoromethylthiolate can also be considered as a source of other trifluoromethylthiolate salts. Indeed, it was reported to react with CuBr 2 to provide the corresponding (trifluoromethylthio)copper(I) 52. This latter species can also be obtained by reduction of bis(trifluoromethyl) disulfide by copper53 or by reaction of finely divided copper on bis(trifluoromethylthio)mercury(II) 45,51.…”

“…This latter species can also be obtained by reduction of bis(trifluoromethyl) disulfide by copper53 or by reaction of finely divided copper on bis(trifluoromethylthio)mercury(II) 45,51. In comparison to mercury(II) and silver(I) reagents, one advantage of (trifluoromethylthio)copper is that it can convert aryl iodides into aryl trifluoromethyl sulfides without any additives (Scheme ) 51,52. Whereas steric factors have little influence on the reaction, electronic factors are important, as electron‐poor aryl iodides gave better yields.…”

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

“…L. M. Yagupol’skii [93–97] developed a related protocol for trifluoromethylsulfanylation of aromatic and heterocyclic compounds using trifluoromethylthiocopper (Scheme 23). …”

“…Trifluoromethylthiocopper is obtained by reaction of CuBr with AgSCF 3 [93,99], the latter is generated from silver fluoride and carbon disulfide [90,100]. …”