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  • Title: N-Heterocyclic carbene-mediated oxidative esterification of aldehydes: ester formation and mechanistic studies.
    Author: Maji B, Vedachalan S, Ge X, Cai S, Liu XW.
    Journal: J Org Chem; 2011 May 06; 76(9):3016-23. PubMed ID: 21449617.
    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.
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