Catalytic Intermolecular Aldehyde-Ketone Coupling via Acyl Phosphonates

DEMİR A. G., Esiringue I., Gollu M., Reis O.

JOURNAL OF ORGANIC CHEMISTRY, vol.74, no.5, pp.2197-2199, 2009 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 74 Issue: 5
  • Publication Date: 2009
  • Doi Number: 10.1021/jo8026627
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2197-2199
  • Middle East Technical University Affiliated: Yes

Abstract

The first catalytic intermolecular aldehyde-ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate-phosphate rearrangement. These anions readily react with activated ketones to form acyloin type coupling in 41-95% yields.