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Oxidation of Alkyl Trifluoroborates: An Opportunity for Tin‐Free Radical Chemistry
Author(s) -
Sorin Geoffroy,
Martinez Mallorquin Rocio,
Contie Yohan,
Baralle Alexandre,
Malacria Max,
Goddard JeanPhilippe,
Fensterbank Louis
Publication year - 2010
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.201004513
Subject(s) - chemistry , alkyl , tin , dimethyl sulfoxide , copper , organic chemistry , combinatorial chemistry , polymer chemistry , medicinal chemistry
Organotrifluoroborates have been oxidized by copper(II) salts and Dess–Martin periodinane via radical intermediates, as evidenced by TEMPO spin‐trapping experiments. This new method of radical generation is compatible with functionalization and CC bond formation through Giese‐type addition reactions (see scheme; DMSO=dimethyl sulfoxide, TEMPO=2,2,6,6‐tetramethyl‐1‐piperidinyloxyl, free radical).