Synthesis of anthranilic acid derivatives through iron-catalyzed ortho amination of aromatic carboxamides with N-chloroamines

Tatsuaki Matsubara, Sobi Asako, Laurean Ilies, Eiichi Nakamura

Research output: Contribution to journalArticle

182 Citations (Scopus)

Abstract

Arenes possessing an 8-quinolinylamide group as a directing group are ortho aminated with N-chloroamines and N-benzoyloxyamines in the presence of an iron/diphosphine catalyst and an organometallic base to produce anthranilic acid derivatives in high yield. The reaction proceeds via iron-catalyzed C-H activation, followed by the reaction of the resulting iron intermediate with N-chloroamine. The choice of the directing group and diphosphine ligand is crucial for obtaining the anthranilic acid derivative with high yield and product selectivity.

Original languageEnglish
Pages (from-to)646-649
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number2
DOIs
Publication statusPublished - Jan 15 2014
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

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