Iron-catalyzed C-C bond formation at α-position of aliphatic amines via C-H bond activation through 1,5-hydrogen transfer

Naohiko Yoshikai, Adam Mieczkowski, Arimasa Matsumoto, Laurean Ilies, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

146 Citations (Scopus)

Abstract

C-C bond formation reactions that take place through organoiron species sometimes exhibit radical-like character. The reaction of N-(2-iodophenylmethyl) dialkylamine with a Grignard or diorganozinc reagent in the presence of a catalytic amount of Fe(acac)3 gives the product resulting from arylation, alkenylation, or alkylation of the sp3 C-H bond next to the amine group in good to excellent yield. Mechanistic studies including labeling experiments indicate that the reaction involves radical translocation triggered by the formation of a radical-like species by removal of the iodide group.

Original languageEnglish
Pages (from-to)5568-5569
Number of pages2
JournalJournal of the American Chemical Society
Volume132
Issue number16
DOIs
Publication statusPublished - 2010 Apr 28
Externally publishedYes

ASJC Scopus subject areas

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

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