Rhodium-catalyzed 1,4-addition of terminal alkynes to vinyl ketones

Ronald V. Lerum, John D. Chisholm

Research output: Contribution to journalArticle

48 Scopus citations

Abstract

The metal complex Rh(acac)(CO) 2 in the presence of an eqimolar amount of tris(o-methoxyphenyl)phosphine provides a useful catalyst system for the 1,4-addition of alkynes to unsubstituted vinyl ketones. Best yields are obtained when the transformation is performed in benzene at reflux with an excess of vinyl ketone. Both aryl and alkyl substituted alkynes participate in the reaction. Primary alcohols and alkyl chlorides are well tolerated under these reaction conditions. The reaction also proceeds in aqueous solvent mixtures, unlike most organometallic addition reactions.

Original languageEnglish (US)
Pages (from-to)6591-6594
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number35
DOIs
StatePublished - Aug 23 2004

Keywords

  • 1,4-Addition
  • Alkyne
  • Rhodium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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