Generation of Acyl Anion Equivalents from Acylphosphonates via Phosphonate—Phosphate Rearrangement: A Highly Practical Method for Cross-Benzoin Reaction

Autor:	Ömer Reis, Iğdir Ac, Ayhan S. Demir, Ilker Esiringu, Serkan Eymur
Rok vydání:	2006
Předmět:	chemistry.chemical_classification Ketone Organic Chemistry General Medicine Phosphate Thiophene derivatives Phosphonate Medicinal chemistry Ion chemistry.chemical_compound Equivalent chemistry Benzoin Organic chemistry lipids (amino acids peptides and proteins) Cyanide anion Nucleoside
Zdroj:	ChemInform. 37
ISSN:	1522-2667 0931-7597
Popis:	[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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5f8862b43b9c008a38c921b9f82030cc https://doi.org/10.1002/chin.200618171 Zobrazit plný text záznamu Plný text