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NHC Catalyzed Oxidations of Aldehydes to Esters: Chemoselective Acylation of Alcohols in Presence of Amines

Suman De Sarkar, Stefan Grimme and Armido Studer*

*NRW Graduate School of Chemistry, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraβe 40, 48149, Münster, Germany, Email: studeruni-muenster.de

S. De Sarkar, S. Grimme, A. Studer, J. Am. Chem. Soc., 2010, 132, 1190-1191.

DOI: 10.1021/ja910540j (free Supporting Information)


Abstract

Cooperative carbene catalysis allows selective oxidative acylations of alcohols with aldehydes even in the presence of amino groups by using a readily available cheap organic oxidant. Quantum chemical calculations support the suggested mechanism.


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Note

Benzoquinone (BQ) can not be used as an oxidant since the reduced form, hydroquinone, would act as a competing nucleophile in the oxidative esterification.

Armido Studer, November 23, 2010


Oxidative Amidation and Azidation of Aldehydes by NHC Catalysis

S. De Sarkar, A. Studer, Org. Lett., 2010, 12, 1992-1995.


Key Words

oxidative esterification, 3,3',5,5'-tetra-tert-butyldiphenoquinone, organocatalysis


ID: J48-Y2010-0250