Premium
Trifluoromethanesulfinyl Chloride for Electrophilic Trifluoromethythiolation and Bifunctional Chlorotrifluoromethythiolation
Author(s) -
Jiang Lvqi,
Yan Qiang,
Wang Rongkang,
Ding Tianqi,
Yi Wenbin,
Zhang Wei
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804027
Subject(s) - bifunctional , chemistry , reagent , disproportionation , chloride , electrophile , catalysis , halide , medicinal chemistry , organic chemistry
Abstract Trifluoromethanesulfinyl chloride (CF 3 SOCl) has been introduced as a new reagent for C−H trifluoromethylthiolation of indoles, thiophenes, and ketones under catalyst‐free conditions and in the absence of reductant. The disproportionation of CF 3 SOCl to CF 3 SO 2 Cl and CF 3 SCl provides two pathways for the trifluoromethylthiolation. Direct trifluoromethylthiolation with CF 3 SCl or trifluoromethylsulfoxidation with CF 3 SOCl is followed by reduction with CF 3 SOCl. This reagent can be used to functionalize benzothiophenes, benzofurans, and indenes under the promotion of Ag 2 CO 3 . It can also be used for trifluoromethylthiolation of thiols and benzeneselenols, and 1,2‐bifunctional chlorotrifluoromethylthiolation of indoles, styrenes, and alkyenes. The method can also be extended for difluorometylthiolation reactions using CF 2 HSOCl.