Intramolecular hydrosilylation and silicon-assisted cross-coupling: An efficient route to trisubstituted homoallylic alcohols

Scott E. Denmark, Pan Weitao

Research output: Contribution to journalArticlepeer-review

Abstract

(equation presented) Alkylidenesilacyclopentanes (formed by intramolecular hydrosilylation of homopropargyl alcohols) are efficiently coupled with aryl or alkenyl halides in the presence of tetrabutylammonium fluoride and a palladium(0) catalyst. Yields of cross-coupling were generally high, and the reaction is compatible with a wide range of functional groups. The overall transformation achieves the conversion of homopropargyl alcohols to trisubstituted homoallylic alcohols in a highly stereoselective fashion.

Original languageEnglish (US)
Pages (from-to)61-64
Number of pages4
JournalOrganic Letters
Volume3
Issue number1
DOIs
StatePublished - Jan 11 2001

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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