title: Hydroacylation of alpha,beta-unsaturated esters via aerobic C-H activation.
abstract: The development of methods for carbon-carbon bond formation under benign conditions is an ongoing challenge for the synthetic chemist. In recent years there has been considerable interest in using selective C-H activation as a direct route for generating reactive intermediates. In this article, we describe the use of aldehyde auto-oxidation as a simple, clean and effective method for C-H activation, resulting in the generation of an acyl radical. This acyl radical can be used for carbon-carbon bond formation and herein we describe the application of this method for the hydroacylation of alpha,beta-unsaturated esters without the requirement of additional catalysts or reagents. This methodology generates unsymmetrical ketones, which have been shown to have broad use in organic synthesis.
authors.affiliation: Department of Chemistry, University College London, London WC1H 0AJ.
authors.forename: Vijay
authors.initials: V
authors.lastname: Chudasama
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Fitzmaurice
authors.forename: Stephen
authors.initials: S
authors.lastname: Caddick
mesh_terms: D000215:Acylation; D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D007659:Ketones / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D000475:Alkenes; D004952:Esters; D007659:Ketones; D002244:Carbon