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Facile Coupling of Aldehydes with Alcohols: An Evolved Tishchenko Process for the Preparation of Unsymmetrical Esters
Author(s) -
Liu Heng,
Eisen Moris S.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700756
Subject(s) - chemistry , ketone , aldehyde , trifluoromethyl , organic chemistry , coupling reaction , process (computing) , combinatorial chemistry , catalysis , computer science , operating system , alkyl
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.