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