Iron-catalyzed stereospecific activation of olefinic C-H bonds with grignard reagent for synthesis of substituted olefins

Laurean Ilies, Sobi Asako, Eiichi Nakamura

Research output: Contribution to journalArticle

102 Citations (Scopus)

Abstract

The reaction of an aryl Grignard reagent with a cyclic or acyclic olefin possessing a directing group such as pyridine or imine results in the stereospecific substitution of the olefinic C-H bond syn to the directing group. The reaction takes place smoothly and without isomerization of the product olefin in the presence of a mild oxidant (1,2-dichloro-2-methylpropane) and an aromatic cosolvent. Several lines of evidence suggest that the reaction proceeds via iron-catalyzed olefinic C-H bond activation rather than an oxidative Mizoroki-Heck-type reaction.

Original languageEnglish
Pages (from-to)7672-7675
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number20
DOIs
Publication statusPublished - May 25 2011

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Iron-catalyzed stereospecific activation of olefinic C-H bonds with grignard reagent for synthesis of substituted olefins'. Together they form a unique fingerprint.

  • Cite this