Beyond benzoin condensation: Trimerization of aldehydes via metal-free aerobic oxidative esterification of aldehydes with benzoin products in the presence of cyanide

Yoo Jin Kim, Na Yeun Kim, Cheol-Hong Cheon

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

An unusual trimerization of aldehydes in the presence of cyanide via metal-free aerobic oxidative esterification under ambient conditions is described. Various aromatic aldehydes provided the corresponding oxidative esterification products in good to excellent yields. Mechanistic studies suggested that this reaction would proceed via a two-step sequence: cyanide-catalyzed benzoin condensation of aldehydes and subsequent aerobic oxidative esterification of aldehydes with the resultant benzoin products. The usefulness of this protocol was further demonstrated by converting the resulting trimeric products into other biologically important compounds.

Original languageEnglish
Pages (from-to)2514-2517
Number of pages4
JournalOrganic Letters
Volume16
Issue number9
DOIs
Publication statusPublished - 2014 May 2

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ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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