Synthesis of meta-substituted anilines via copper-catalyzed [1,3]-methoxy rearrangement

Itaru Nakamura, Hiroki Tashiro, Yasuhiro Ishida, Masahiro Terada

Research output: Contribution to journalArticle

Abstract

meta-Substituted anilines were efficiently synthesized via copper-catalyzed [1,3]-methoxy rearrangement of N-methoxyanilines followed by Michael addition of nucleophiles to the in situ generated ortho-quinol imine. The present reaction exhibits excellent applicability of para-substituents, such as vinyl, methylthio, ester, and bromo, and carbon nucleophiles, such as 1,3,5-trimethoxybenzene, N-methylindole, and dimethyl malonate. Thus, the present rearrangement can resolve problems stemming from oxidation reactions, such as the use of stoichiometric amounts of oxidants and low compatibility of electron-withdrawing groups.

Original languageEnglish
Pages (from-to)3794-3798
Number of pages5
JournalOrganic letters
Volume22
Issue number10
DOIs
Publication statusPublished - 2020 May 15

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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