Oxidative Homologation of Aldehydes to α??Ketoaldehydes by using Iodoform, o??Iodoxybenzoic Acid, and Dimethyl Sulfoxide

A Zall, D Bensinger, B Schmidt

Index: Zall, Andrea; Bensinger, Dennis; Schmidt, Boris European Journal of Organic Chemistry, 2012 , # 7 p. 1439 - 1447

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Citation Number: 5

Abstract

Abstract An efficient three-step synthetic route to α-ketoaldehydes starting from aryl aldehydes is reported. The aldehydes were treated with iPrMgCl and iodoform to obtain β- diiodoalcohols, which were then oxidized with o-iodoxybenzoic acid at room temperature to the corresponding β-diiodoketones. Subsequent reaction of the β-diiodoketone to the α- ketoaldehyde occurred under oxygen transfer from dimethyl sulfoxide. These sensitive ...

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