Cationic N-Heterocyclic Carbene Copper-Catalyzed [1,3]-Alkoxy Rearrangement of N-Alkoxyanilines

Itaru Nakamura, Takeru Jo, Yasuhiro Ishida, Hiroki Tashiro, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

The [1,3]-alkoxy rearrangement reactions of N-alkoxyanilines were efficiently catalyzed by cationic N-heterocyclic carbene (NHC)-Cu catalysts in affording 2-alkoxyaniline derivatives in good to excellent yields with high functional group compatibility. For N-alkoxyanilines having an electron-withdrawing substituent at the meta-position, the alkoxy group selectively migrated to the more hindered ortho-position. In contrast, the alkoxy group migrated to the less hindered ortho-position for N-alkoxyanilines having an electron-donating substituent. Mechanistic studies suggest that the rearrangement reactions proceed via an intramolecular route.

Original languageEnglish
Pages (from-to)3059-3062
Number of pages4
JournalOrganic letters
Volume19
Issue number12
DOIs
Publication statusPublished - 2017 Jun 16

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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