title: 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.
authors: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371.
authors: Biswajit
authors: B
authors: Maji
authors: Seenuvasan
authors: S
authors: Vedachalan
authors: Xin
authors: X
authors: Ge
authors: Shuting
authors: S
authors: Cai
authors: Xue-Wei
authors: XW
authors: Liu
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001565:Benzoates / Q000737:chemistry; D002384:Catalysis; D002934:Cinnamates / Q000737:chemistry; D004951:Esterification; D004952:Esters; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D001565:Benzoates; D002934:Cinnamates; D004952:Esters; D006571:Heterocyclic Compounds; C030011:carbene; D009584:Nitrogen; D008697:Methane