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

44 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

Fingerprint

Acrylamides
Alkylation
Alkenes
Organometallics
Oxidants
Olefins
Hydrogen
Iron
Chemical activation
Catalysts

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Iron-Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides. / Ilies, Laurean; Ichikawa, Saki; Asako, Sobi; Matsubara, Tatsuaki; Nakamura, Eiichi.

In: Advanced Synthesis and Catalysis, Vol. 357, No. 10, 01.07.2015, p. 2175-2179.

Research output: Contribution to journalArticle

Ilies, L, Ichikawa, S, Asako, S, Matsubara, T & Nakamura, E 2015, 'Iron-Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides', Advanced Synthesis and Catalysis, vol. 357, no. 10, pp. 2175-2179. https://doi.org/10.1002/adsc.201500276
Ilies, Laurean ; Ichikawa, Saki ; Asako, Sobi ; Matsubara, Tatsuaki ; Nakamura, Eiichi. / Iron-Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides. In: Advanced Synthesis and Catalysis. 2015 ; Vol. 357, No. 10. pp. 2175-2179.
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