Tin-Free Radical Acylation Reactions with Methanesulfonyl Oxime Ether

Abstract

A simple strategy involving thermal decomposition of the methanesulfonyl radical into the methyl radical and the subsequent transfer of an iodine atom or phenyl telluride group was used to develop a tin-free radical acylation reaction (see scheme; V-40=1,1'-azobis(cyclohexane-1-carbonitrile). The key was finding reaction conditions under which the I or PhTe transfer is faster than the direct addition of the alkyl radical to the methanesulfonyl oxime ether.

Keywords: C−C coupling; acylation; radical reactions; synthetic methods.