Mechanistic studies of nickel(II)-catalyzed direct alcoholysis of 8-aminoquinoline amides

Hiroyuki Morimoto, Walaa Akkad, Toru Deguchi, Takashi Ohshima

Research output: Contribution to journalArticle

Abstract

This paper describes the mechanistic aspects of nickel(II)-catalyzed direct alcoholysis of 8-aminoquinoline amides. Kinetic experiments suggested that the nickel(II) catalyst existed in an oligomeric form in the resting state, and the 8-aminoquinoline generated after cleavage coordinated to the nickel(II) catalyst to decelerate the reaction. In addition, density functional theory calculations revealed that the reactions proceeded via the intermediate with N,N,O-tridentate coordination of 8-aminoquinoline amides to the nickel(II) metal center, and that the alcoholysis reaction did not involve deprotonation of the N-H bond of 8-aminoquinoline amides, in contrast to the proposed mechanism for C-H bond functionalization reactions of 8-aminoquinoline amides.

Original languageEnglish
Pages (from-to)471-485
Number of pages15
JournalHeterocycles
Volume101
Issue number2
DOIs
Publication statusPublished - Jan 1 2020

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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