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)
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.
see article for more examples
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.