Hydroacylation of α,β-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 α,β-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. The development of benign methods for carbon–carbon bond formation is a continuing challenge. Here, a simple procedure for the hydroacylation of α,β-unsaturated esters is described, in which auto-oxidation of aldehydes and subsequent acyl radical addition to α,β-unsaturated esters occurs without the need for additional reagents.

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Chudasama, V., Fitzmaurice, R. & Caddick, S. Hydroacylation of α,β-unsaturated esters via aerobic C–H activation. Nature Chem 2, 592–596 (2010). https://doi.org/10.1038/nchem.685

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