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Direct Catalytic Trifluoromethylthiolation of Boronic Acids and Alkynes Employing Electrophilic Shelf‐Stable N ‐(trifluoromethylthio)phthalimide
Author(s) -
Pluta Roman,
Nikolaienko Pavlo,
Rueping Magnus
Publication year - 2014
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.201307484
Subject(s) - phthalimide , reagent , chemistry , electrophile , catalysis , organic synthesis , combinatorial chemistry , organic chemistry
A new and safe method for the synthesis of N ‐(trifluoromethylthio)phthalimide, a convenient and shelf‐stable reagent for the direct trifluoromethylthiolation, has been developed. N ‐(Trifluoromethylthio)phthalimide can be used as an electrophilic source of F 3 CS + and reacts readily with boronic acids and alkynes under copper catalysis. The utility of CF 3 S‐containing molecules as biologically active agents, the mild reaction conditions employed, and the high tolerance of functional groups demonstrate the potential of this new methodology to be widely applied in organic synthesis as well as industrial pharmaceutical and agrochemical research and development.