A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate

Abstract

Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01–0.1 mol% Bi(OTf)3·xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3·Et2O, currently used to effect epoxide rearrangements. © 2001 Elsevier Science Ltd. All rights reserved.