Tetrahedron Letters

Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides

V Pace, L Castoldi, W Holzer

Index: Pace, Vittorio; Castoldi, Laura; Holzer, Wolfgang Tetrahedron Letters, 2012 , vol. 53, # 8 p. 967 - 972

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Citation Number: 9

Abstract

A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (ie, 2-haloallyl) that per se could interact with ...