Nucleophilic acylation of o-quinone methides: An umpolung strategy for the synthesis of α-aryl ketones and benzofurans

Anita E. Mattson, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

84 Scopus citations

Abstract

The synthesis of α-aryl ketones is accomplished by the direct nucleophilic acylation of o-quinone methide electrophiles. In this process, two reactive intermediates, carbonyl anions and o-quinone methides, are generated in one flask upon treatment of the corresponding thiazolium carbinols and silyl protected phenols with a soluble fluoride source. These intermediates then undergo productive addition reactions to afford the desired α-aryl ketone adducts. This new strategy has been applied to a short synthesis of the natural product demethylmoracin I.

Original languageEnglish (US)
Pages (from-to)4508-4509
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number15
DOIs
StatePublished - Apr 18 2007

ASJC Scopus subject areas

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

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