Unusual homocoupling in the reaction of diorganocuprates with an allylic halide

Jakob Norinder, Jan E. Bäckvall, Naohiko Yoshikai, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

The reactions of dialkyl- and diarylcuprates (R 2CuM; M = Li, MgBr) with perfluoroallyl iodide were found to give the homocoupling products R-R as the only product of C-C bond formation. Density functional calculations revealed that the perfluoroallyl ligand, being strongly electron-withdrawing and less Lewis basic, significantly changes the electronic properties of the allylcopper(III) intermediate and acts as a spectator ligand in the reductive elimination.

Original languageEnglish
Pages (from-to)2129-2132
Number of pages4
JournalOrganometallics
Volume25
Issue number9
DOIs
Publication statusPublished - 2006 Apr 24
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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