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

Heng Liu; Moris S. Eisen

doi:10.1002/ejoc.201700756

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 journal › Article › peer-review

11 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 language	English
Pages (from-to)	4852-4858
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	32
DOIs	https://doi.org/10.1002/ejoc.201700756
State	Published - 1 Sep 2017
Externally published	Yes

Keywords

Alcohols
Aldehydes
Esterification
Reaction mechanisms
Synthetic methods

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10.1002/ejoc.201700756

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

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.",

keywords = "Alcohols, Aldehydes, Esterification, Reaction mechanisms, Synthetic methods",

author = "Heng Liu and Eisen, {Moris S.}",

note = "Publisher Copyright: {\textcopyright} 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

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T1 - Facile Coupling of Aldehydes with Alcohols

T2 - An Evolved Tishchenko Process for the Preparation of Unsymmetrical Esters

AU - Liu, Heng

AU - Eisen, Moris S.

PY - 2017/9/1

Y1 - 2017/9/1

N2 - 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.

AB - 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.

KW - Alcohols

KW - Aldehydes

KW - Esterification

KW - Reaction mechanisms

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=85028614056&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201700756

DO - 10.1002/ejoc.201700756

M3 - 文章

AN - SCOPUS:85028614056

SN - 1434-193X

VL - 2017

SP - 4852

EP - 4858

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 32

ER -

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

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Keywords

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