Facile Coupling of Aldehydes with Alcohols: An Evolved Tishchenko Process for the Preparation of Unsymmetrical Esters

Heng Liu, Moris S. Eisen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A facile coupling process between aldehydes and alcohols to afford unsymmetrical esters is presented herein. This transformation is complementary to the Tishchenko reaction and provides access to unsymmetrical esters under very mild conditions. Various aldehydes and alcohols are suitable in this reaction, and the addition of a sacrificial trifluoromethyl ketone allows the process to take place in a highly selective manner. A plausible mechanism based on details obtained by monitoring the reaction progress and deuterium-labeling studies has been proposed.

Original languageEnglish
Pages (from-to)4852-4858
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number32
DOIs
StatePublished - 1 Sep 2017
Externally publishedYes

Keywords

  • Alcohols
  • Aldehydes
  • Esterification
  • Reaction mechanisms
  • Synthetic methods

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