N-heterocyclic carbene-catalyzed conjugate additions of alcohols

Eric M. Phillips, Matthias Riedrich, Karl A. Scheidt

Research output: Contribution to journalArticle

157 Scopus citations

Abstract

An efficient intermolecular conjugate addition of alcohols to activated alkenes catalyzed by N-heterocyclic carbenes has been developed. With 5 mol % of the free carbene derived from IMes•HCl, unsaturated ketones and esters are competent substrates, and a variety of primary and secondary alcohols can be employed as the nucleophile. No oligomerization is observed under these mild conditions for effective hydroalkoxylation. In addition to reactions with activated alkenes, IMes catalyzes the formation of vinyl ethers through the 1,4-addition of alcohols to ynones and promotes tandem conjugate addition/Michael cascade reactions. Preliminary data support a Brønsted base mechanism with the free carbene.

Original languageEnglish (US)
Pages (from-to)13179-13181
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number38
DOIs
StatePublished - Sep 29 2010

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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