Phase-transfer catalysed ion-radical perfluoroalkylation of thiols

Structure, Reactivity, and Chemistry of Fluoroalkyl Radicals

“…Following early work carried out photolytically in liquid ammonia, recent reports have indicated that good yields of substitution products can be obtained in polar solvents at room temperature, without irradiation. [268][269][270][271][272][273] Perfluoro selenides and tellurides [274][275][276] and perfluoroalkyl sulfinates 277,278 are also synthetically accessible via similar processes:…”

“…Whereas it has been demonstrated that both malonate ions and thiolate ions can catalyze the free radical chain addition reaction of perfluoroalkyl iodides to olefins, , under appropriate conditions one can obtain products deriving from substitution in such processes. Following early work carried out photolytically in liquid ammonia, recent reports have indicated that good yields of substitution products can be obtained in polar solvents at room temperature, without irradiation. −

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Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid

“…There are many methods about the synthesis of aryltrifluoromethylsulfides [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. Thereinto, the reaction of aryl disulfide with trifluoromethyl bromide in the presence of sulfoxylate anion radical precursors developed by Wakselman et al [23,24] constitute an important method of synthesis.…”

Nucleophilic difluoromethylation and trifluoromethylation using tetrakis(dimethylamino)ethylene (TDAE) reagent

“…The first is the classic S RN 1 reaction of aryl thiolates with CF 3 I or CF 3 Br. This method first reported by Yaguploskii using CF 3 I and UV irradiation in 1977 [36], by Wakselman and Tordeux using CF 3 Br in 1984 [37], along with later variations [38,39], has proved to be generally useful when using aryl thiolates but less efficient when using alkanethiolates [40]. The CF 3 I/TDAE reagent proves to be an excellent choice for the conversion of aryl and alkyl disulfides into their trifluoromethyl thioethers.…”