Generation of acyl anion equivalents from acylphosphonates via phosphonate-phosphate rearrangement: A highly practical method for cross-benzoin reaction


Demir A., Reis O., Igdir A., Esiringu I., Eymur S.

JOURNAL OF ORGANIC CHEMISTRY, vol.70, no.25, pp.10584-10587, 2005 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 70 Issue: 25
  • Publication Date: 2005
  • Doi Number: 10.1021/jo051811u
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.10584-10587

Abstract

Acylphosphonates are potent acyl anion precursors that generate acyl anion equivalents under the promotion of cyanide anion via phosphonate-phosphate rearrangement. These anions readily react with aldehydes to provide cross-benzoin products. In this way it is possible to synthesize a variety of aromatic-aromatic, aromatic-aliphatic, and aliphatic-aromatic benzoins. Moreover the reaction of benzoylphosphonate with potent electrophile 2,2,2-trifluoroacetophenone provided the corresponding aldehyde-ketone coupling product in high yield.