Oxidative Cleavage of Alkenes Using an In Situ Generated Iodonium Ion with Oxone as a Terminal Oxidant
摘要:
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 Ozone 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.
Oxidative Cleavage of Alkenes Using an In Situ Generated Iodonium Ion with Oxone as a Terminal Oxidant
作者:Prem P. Thottumkara、Thottumkara K. Vinod
DOI:10.1021/ol1023807
日期:2010.12.17
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 Ozone 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.