An Example of the Persistent Radical Effect in Cobaloxime-Mediated Radical Alkyl-Alkenyl Cross Coupling

Bruce P. Branchaud, Gui Xue Yu

Research output: Contribution to journalArticle

22 Scopus citations

Abstract

Photolysis of alkylcobaloximes in the presence of activated alkenes results in both β-H elimination and alkyl–alkenyl cross coupling. A proposed mechanism predicts that buildup of the persistent radical ⋅CoII- (dmgH)2py as the reactions proceed enhances β-H elimination, lowering the yield of cross coupling. Scavengers of ⋅CoII(dmgH)2py suppress β-H elimination and enhance cross coupling, presumably by lowering the concentration of ⋅CoII(dmgH)2py. These data provide support for the proposed reaction mechanism and illustrate how a persistent radical can control product distributions in an organometallic radical reaction.

Original languageEnglish (US)
Pages (from-to)4262-4264
Number of pages3
JournalOrganometallics
Volume12
Issue number11
DOIs
StatePublished - Jan 1 1993

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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