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Trifluoromethylthiolation and Trifluoromethylselenolation of α‐Diazo Esters Catalyzed by Copper
Author(s) -
Matheis Christian,
Krause Thilo,
Bragoni Valentina,
Goossen Lukas J.
Publication year - 2016
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.201602730
Subject(s) - diazo , thiocyanate , copper , catalysis , thio , chemistry , molecule , trifluoromethyl , combinatorial chemistry , organic chemistry , alkyl
α‐Diazo esters are smoothly converted into the corresponding trifluoromethyl thio‐ or selenoethers by reaction with Me 4 NSCF 3 or Me 4 NSeCF 3 , respectively, in the presence of catalytic amounts of copper thiocyanate. This straightforward method gives high yields under neutral conditions at room temperature and is applicable to a wide range of functionalized molecules, including diverse α‐amino acid derivatives. It is well‐suited for the late‐stage introduction of trifluoromethylthio or ‐seleno groups into drug‐like molecules.