Generation of Acyl Anion Equivalents from Acylphosphonates via Phosphonate−Phosphate Rearrangement:  A Highly Practical Method for Cross-Benzoin Reaction

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 arom...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-12, Vol.70 (25), p.10584-10587
Main Authors: Demir, Ayhan S, Reis, Ömer, İǧdir, A. Çiǧdem, Esiringü, İlker, Eymur, Serkan
Format: Article
Language:English
Subjects:
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051811u