4.7 Article

Catalytic Intermolecular Aldehyde-Ketone Coupling via Acyl Phosphonates

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 5, Pages 2197-2199

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo8026627

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Funding

  1. Scientific and Technological Research Council of Turkey (TUBITAK)
  2. Turkish Academy of Science (TOBA),
  3. Middle East Technical University (METU)
  4. Turkish State Planning Organization

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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.

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