Direct Catalytic Alcoholysis of Unactivated 8-Aminoquinoline Amides

Toru Deguchi, Hai Long Xin, Hiroyuki Morimoto, Takashi Ohshima

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

Direct catalytic alcoholysis of unactivated amides is one of the most difficult challenges in organic chemistry, and an applicable method for cleaving amides used as directing groups in regioselective functionalization reactions has not been reported. Herein, we report direct catalytic alcoholysis of 8-aminoquinoline amides, which are highly effective directing groups in regioselective functionalization reactions. The reactions proceeded with a simple combination of substrates, air-stable catalysts, and alcohols, affording the corresponding esters in good yields with broad functional group tolerance. Highly chemoselective cleavage of the 8-aminoquinoline amides in the presence of related carbonyl functionalities and preliminary mechanistic studies are also described.

Original languageEnglish
Pages (from-to)3157-3161
Number of pages5
JournalACS Catalysis
Volume7
Issue number5
DOIs
Publication statusPublished - May 5 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Direct Catalytic Alcoholysis of Unactivated 8-Aminoquinoline Amides'. Together they form a unique fingerprint.

  • Cite this