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Novel radical alkylation of carboxylic imides
Sunggak Kim1, Chae Jo Lim, Changsik Song
1Center for Molecular Design & Synthesis and Department of Chemistry, School of Molecular Science, Korea Advanced Institute of Science and Technology, Taejon 305-701, Korea. skim@mail.kaist.ac.kr
Abstract:
Although alkylation is one of the most important and fundamental organic reactions, radical-mediated alkylations of carboxylic acid derivatives have not been well studied. The first successful radical alkylation of carboxylic imides is achieved by the addition of an alkyl radical to a ketene O,N-acetal and the subsequent cleavage of N-O bond. It is noteworthy that alkyl halides activated with an electron-withdrawing group undergo alkylations under tin-free conditions due to 1,2-phenyl transfer from silyl to oxygen.
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