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

Hiroyuki Morimoto, Walaa Akkad, Toru Deguchi, Takashi Ohshima

研究成果: Contribution to journalArticle査読

2 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)471-485
ページ数15
ジャーナルHeterocycles
101
2
DOI
出版ステータス出版済み - 1 1 2020

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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