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

180 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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Chloramines
Amination
Iron
Derivatives
Acids
Organometallics
Chemical activation
Ligands
Catalysts
anthranilic acid

ASJC Scopus subject areas

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

Cite this

Synthesis of anthranilic acid derivatives through iron-catalyzed ortho amination of aromatic carboxamides with N-chloroamines. / Matsubara, Tatsuaki; Asako, Sobi; Ilies, Laurean; Nakamura, Eiichi.

In: Journal of the American Chemical Society, Vol. 136, No. 2, 15.01.2014, p. 646-649.

Research output: Contribution to journalArticle

Matsubara, Tatsuaki ; Asako, Sobi ; Ilies, Laurean ; Nakamura, Eiichi. / Synthesis of anthranilic acid derivatives through iron-catalyzed ortho amination of aromatic carboxamides with N-chloroamines. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 2. pp. 646-649.
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