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Synthesis of Difluoromethyl Thioethers from Difluoromethyl Trimethylsilane and Organothiocyanates Generated In Situ
Author(s) -
Bayarmagnai Bilguun,
Matheis Christian,
Jouvin Kévin,
Goossen Lukas J.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201500899
Subject(s) - chemistry , thiocyanate , halide , substituent , alkyl , in situ , copper , trimethylsilane , combinatorial chemistry , organic chemistry
A copper‐CF 2 H complex generated in situ from copper thiocyanate and TMSCF 2 H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one‐pot protocols, allowing late‐stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts. This strategy enables the introduction of difluoromethylthio groups—a largely unexplored substituent with highly promising properties—into drug‐like molecules.