Organic Letters 2010-12-17

Oxidative cleavage of alkenes using an in situ generated iodonium ion with oxone as a terminal oxidant.

Prem P Thottumkara, Thottumkara K Vinod

Index: Org. Lett. 12(24) , 5640-3, (2010)

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Abstract

A facile and operationally convenient catalytic procedure for oxidative cleavage of alkenes is described. In situ formed [hydroxy(4-carboxyphenyl)iodonium]ion, 2, from the oxidation of 4-iodobenzoic acid, 1, has been shown to facilitate the cleavage of a variety of alkenes in presence of Oxone as a co-oxidant. Optimization of the reaction conditions using 1-phenyl-1-cyclohexene, 3, and the competitive oxidative cleavage of different substrates using the optimized conditions has uncovered important mechanistic details of the reaction.