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

被引：81

作者：

Demir, AS ^{[1
]}

Reis, Ö ^{[1
]}

Igdir, AÇ ^{[1
]}

Esiringü, I ^{[1
]}

Eymur, S ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 25期

关键词：

D O I：

10.1021/jo051811u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：10584 / 10587

页数：4

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