Copper-Catalyzed Electrophilic Amidation of Organotrifluoroborates with Use of N-Methoxyamides

Shona Banjo, Eiko Nakasuji, Tatsuhiko Meguro, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A copper-catalyzed electrophilic amidation of aryltrifluoroborates with use of N-methoxyamides is reported. The reaction shows high functional group compatibility derived from two distinct features: 1) the high stability of the N-methoxyamides and 2) the nonbasic mild conditions in the presence of LiCl. The developed method can also be applied to the synthesis of enamides, which are widely distributed in natural products. Preliminary mechanistic studies suggest that the initial step is the transmetalation of the aryltrifluoroborate by the assistance of LiCl, and the resulting aryl copper intermediate provides the anilide through non-SN2 oxidative addition to the N-methoxyamide and subsequent reductive elimination.

Original languageEnglish
Pages (from-to)7941-7947
Number of pages7
JournalChemistry - A European Journal
Volume25
Issue number33
DOIs
Publication statusPublished - 2019 Jun 12

    Fingerprint

Keywords

  • amides
  • copper catalyst
  • electrophilic reaction
  • enamides
  • organotrifluoroborates
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this