Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates

Satoshi Ueno, Naoto Chatani, Fumitoshi Kakiuchi

Research output: Contribution to journalArticle

137 Citations (Scopus)

Abstract

The RuH2(CO)(PPh3)3-catalyzed reaction of 2-amino-6-methylacetophenone with phenylboronic acid 2,2-dimethyl-1,3-propanediol ester in refluxing toluene gave the corresponding phenylation product in 83% yield via aryl carbon-nitrogen bond cleavage. This reaction involves two notable features: (1) the coupling proceeds via the oxidative addition of an aryl carbon-nitrogen bond in anilines to the ruthenium complex, and (2) C-C bond formation takes place via transmetalation between the Ru-NR2 species and organoboronates.

Original languageEnglish
Pages (from-to)6098-6099
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number19
DOIs
Publication statusPublished - 2007 May 16

ASJC Scopus subject areas

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

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