N-Heterocyclic carbene-mediated oxidative esterification of aldehydes: ester formation and mechanistic studies.

Abstract

An unexpected N-heterocyclic carbene-catalyzed esterification of α,β-unsaturated aldehydes including aromatic aldehydes with reactive cinnamyl bromides in the presence of air oxygen or MnO(2) as an oxidant is described. In the presence of oxygen, halogenated and electron-deficient aldehydes react smoothly to furnish esters in good yields. Great efforts have been made on mechanistic studies to deduce a plausible mechanism, based on the experimental results and isotopic labeling experiment.

DOI: 10.1021/jo200275c

Cite this paper

@article{Maji2011NHeterocyclicCO, title={N-Heterocyclic carbene-mediated oxidative esterification of aldehydes: ester formation and mechanistic studies.}, author={Biswajit Maji and Seenuvasan Vedachalan and Xin Ge and Shuting Cai and Xue-Wei Liu}, journal={The Journal of organic chemistry}, year={2011}, volume={76 9}, pages={3016-23} }