Novel radical alkylation of carboxylic imides.
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.
Kim
Sunggak
S
Center 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
Lim
Chae Jo
CJ
Song
Changsik
C
Chung
Won-Jin
WJ