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, cilt.70, sa.25, ss.10584-10587, 2005 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 70 Sayı: 25
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1021/jo051811u
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.10584-10587
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.