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N-Heterocyclic Carbene-Catalyzed Oxidation of Unactivated Aldehydes to Esters

Brooks E. Maki and Karl A. Scheidt*

*Department of Chemistry, Northwestern University, Evanston, Illinois 60208, Email: scheidtnorthwestern.edu

B. E. Marki, K. A. Scheidt, Org. Lett., 2008, 10, 4331-4334.

DOI: 10.1021/ol8018488 (free Supporting Information)


Abstract

N-Heterocyclic carbenes catalyze the oxidation of unactivated aldehydes to esters with manganese(IV) oxide in excellent yield under mild conditions. The reaction proceeds through a transient activated alcohol generated in situ and preserves stereochemical integrity. Various esters can be synthesized using a broad range of alcohols and unactivated aldehydes.

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proposed reaction pathway



Tandem Oxidation of Allylic and Benzylic Alcohols to Esters Catalyzed by N-Heterocyclic Carbenes

B. E. Maki, A. Chan, E. M. Phillips, K. A. Scheidt, Org. Lett., 2007, 9, 371-374.


Key Words

oxidative esterification, manganese(IV) oxide, organocatalysis


ID: J54-Y2008-2800