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Oxidative Amidation and Azidation of Aldehydes by NHC Catalysis

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

DOI: 10.1021/ol1004643 (free Supporting Information)


Abstract

A N-heterocyclic carbene catalyzes the oxidative esterification of various aldehydes in the presence of 3,3',5,5'-tetra-tert-butyldiphenoquinone to yield hexafluoroisopropylesters, which are useful active esters for in situ amide bond formation. This transition metal-free organocatalytic system also enabled a mild oxidative azidation of aldehydes.

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

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


Key Words

amides, acyl azides, 3,3',5,5'-tetra-tert-butyldiphenoquinone, organocatalysis


ID: J54-Y2010-0280