A palladium-mediated tandem carbon-carbon bond forming method featuring nucleophilic substitution of intermediate π-allylpalladium complexes produced via the heck reaction

Christine S. Nylund, Daniel T. Smith, John M. Klopp, Steven M. Weinreb

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

Carbon nucleophiles are alkylated with π-allylpalladium complexes formed by the palladium-catalyzed Heck reaction of a vinyl bromide and an olefin. This methodology achieves the consecutive formation of two carbon-carbon bonds in one simple operation and can be applied both inter- and intramolecularly. The rapid construction of functionalized carbobicyclic compounds is effected by the intramolecular version of this condensation.

Original languageEnglish (US)
Pages (from-to)9301-9318
Number of pages18
JournalTetrahedron
Volume51
Issue number34
DOIs
StatePublished - Aug 21 1995

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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