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Radical Desulfur‐Fragmentation and Reconstruction of Enol Triflates: Facile Access to α‐Trifluoromethyl Ketones
Author(s) -
Su Xiaolong,
Huang Honggui,
Yuan Yaofeng,
Li Yi
Publication year - 2017
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.201608507
Subject(s) - enol , trifluoromethanesulfonate , regioselectivity , fragmentation (computing) , chemistry , trifluoromethyl , radical , medicinal chemistry , radical ion , photochemistry , combinatorial chemistry , organic chemistry , catalysis , computer science , alkyl , operating system , ion
We report an efficient oxidative radical desulfur‐fragmentation and reconstruction of enol triflates for the synthesis of α‐CF 3 ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF 3 radical from the triflyl group of enol triflate and subsequent addition of the CF 3 radical to another enol triflate form the desired α‐CF 3 ketones. This method provides a new approach to α‐CF 3 ketones, featuring the utilization of catalytic amount of oxidants, broad substrate scope, and potential to control the regioselectivity.