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: scheidt
northwestern.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.
see article for more examples
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
