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2009•The Journal of Organic ChemistryOpen access

Catalytic Intermolecular Aldehyde−Ketone Coupling via Acyl Phosphonates

Ayhan Sıtkı DEMİR, lker Esiringü, Mehmet Göllü, Ömer Reis

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Abstract

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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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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Available abstract

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.

Key concepts: Chemistry, Phosphonate, Aldehyde, Ketone, Catalysis, Intermolecular force, Cyanide, Organic chemistry

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