AI Article Synopsis
- Acylphosphonates act as strong acyl anion precursors when they react with cyanide anion, leading to a rearrangement that produces acyl anion equivalents.
- These anions can then react with aldehydes to create various cross-benzoin products, enabling the synthesis of different aromatic and aliphatic compounds.
- A specific reaction involving benzoylphosphonate and 2,2,2-trifluoroacetophenone results in a high yield of an aldehyde-ketone coupling product.
Article Abstract
[reactions: see text] 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.
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