23522-65-8Relevant articles and documents
N-Heterocyclic carbene-catalyzed oxidations
Maki, Brooks E.,Chan, Audrey,Phillips, Eric M.,Scheidt, Karl A.
experimental part, p. 3102 - 3109 (2009/09/05)
N-Heterocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized, including protected carboxylates. The oxidation proceeds under mild conditions, with low loadings of a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.