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Catalytic Intermolecular Aldehyde-Ketone Coupling via Acyl Phosphonates
Date
2009-03-06
Author
Demir, Ayhan Gürbüz
Esiringue, Iker
Gollu, Mehmet
Reis, Oemer
Metadata
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This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
.
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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.
Subject Keywords
Nucleophilic acylation
,
Donor
,
Rearrangement
,
Acylphosphonates
,
Benzoin reactions
,
Anion equivalents
URI
https://hdl.handle.net/11511/62945
Journal
JOURNAL OF ORGANIC CHEMISTRY
DOI
https://doi.org/10.1021/jo8026627
Collections
Department of Educational Sciences, Article