Catalytic Intermolecular Aldehyde-Ketone Coupling via Acyl Phosphonates
JOURNAL OF ORGANIC CHEMISTRY, vol.74, no.5, pp.2197-2199, 2009 (SCI-Expanded, Scopus)
- 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.