Three-component coupling reactions of alkyl iodides, 1,3-dienes, and carbonyl compounds by sequential generation of radical and anionic species with CrCl2

Kazuhiko Takai, N. Matsukawa, A. Takahashi, T. Fujii

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Abstract

The mild reductant chromium(II) chloride can discriminate between alkyl iodides, alkyl radicals, and allylic radicals. In the presence of Cr(II) the alkyl radical is so long-lived that it can undergo intermolecular addition to a 1,3-diene. Rapid one-electron reduction of the formed allylic radical results in an allylic chromium(II) species, which adds to an aldehyde to afford a three-component coupling product.

Original languageEnglish
Pages (from-to)152-155
Number of pages4
JournalAngewandte Chemie - International Edition
Volume37
Issue number1-2
Publication statusPublished - 1998

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Keywords

  • Chromium
  • Radical reactions
  • Synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)

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