Iron-Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides

Laurean Ilies, Saki Ichikawa, Sobi Asako, Tatsuaki Matsubara, Eiichi Nakamura

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Alkenes and arenes possessing a bidentate directing group are alkylated with a primary or secondary alkylzinc halide in the presence of an iron/diphosphine catalyst and a dichloroalkane oxidant. Acrylamides, including unsubstituted and monosubstituted ones, react stereoselectively. Under these reaction conditions, β-hydrogen elimination and homocoupling of the organometallic reagent are largely suppressed. The reaction may proceed through C-H activation catalyzed by an organoiron(III) species.

Original languageEnglish
Pages (from-to)2175-2179
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number10
DOIs
Publication statusPublished - Jul 1 2015

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Keywords

  • alkylation
  • amides
  • C-H activation
  • iron
  • zinc

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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