C-C Bond Cleavage of Unactivated 2-Acylimidazoles

Hai Long Xin, Bo Pang, Jeesoo Choi, Walaa Akkad, Hiroyuki Morimoto, Takashi Ohshima

Research output: Contribution to journalArticlepeer-review

Abstract

2-Acylimidazoles are widely used as post-Transformable carboxylic acid equivalents in chemoselective and enantioselective reactions. Their transformations, however, require pretreatment with highly reactive, toxic methylating reagents to facilitate C-C bond cleavage. Here, we demonstrate that such pretreatment can be avoided and the C-C bond cleaved under neutral conditions without the use of additional reagents or catalysts. The scope of the reaction, including the use of products reported in the literature as substrates, and some mechanistic insights are described.

Original languageEnglish
Pages (from-to)11592-11606
Number of pages15
JournalJournal of Organic Chemistry
Volume85
Issue number18
DOIs
Publication statusPublished - Sep 18 2020

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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