Chudasama, V; Fitzmaurice, RJ; Caddick, S; (2010) Hydroacylation of alpha,beta-unsaturated esters via aerobic C-H activation. NAT CHEM , 2 (7) 592 - 596. 10.1038/NCHEM.685.
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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.
|Title:||Hydroacylation of alpha,beta-unsaturated esters via aerobic C-H activation|
|Keywords:||N-HYDROXYPHTHALIMIDE, ORGANIC-SYNTHESIS, MOLECULAR-OXYGEN, ALDEHYDES, BENZALDEHYDE, RADICALS, ALKENES, EPOXIDATION, COMPLEXES, CHEMISTRY|
|UCL classification:||UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry|
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