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Metal‐Free Difluoromethylthiolation, Trifluoromethylthiolation, and Perfluoroalkylthiolation with Sodium Difluoromethane‐ sulfinate, Sodium Trifluoromethanesulfinate or Sodium Perfluoro‐ alkanesulfinate
Author(s) -
Yan Qiang,
Jiang Lvqi,
Yi Wenbin,
Liu Qiran,
Zhang Wei
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700270
Subject(s) - chemistry , difluoromethane , electrophile , sodium , regioselectivity , metal , medicinal chemistry , inorganic chemistry , polymer chemistry , combinatorial chemistry , organic chemistry , catalysis , refrigerant , mechanical engineering , engineering , gas compressor
A method for direct difluoromethylthiolation of Ar−H bonds is introduced. The stable and easy‐to‐handle HCF 2 SO 2 Na is reduced with (EtO) 2 P(O)H in the presence of TMSCl to generate HCF 2 S + for the regioselective difluoromethylthiolation of aromatic compounds including indoles, pyrroles, and activated benzenes. This method is also applicable for the trifluoromethylthiolation with CF 3 SO 2 Na and the perfluoroalkylthiolation with R f SO 2 Na of arenes and heteroarenes. Reaction mechanisms associated with the metal‐free electrophilic fluoroalkylthiolation reactions are also discussed.