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J Am Chem Soc. 2008 Nov 19;130(46):15254-5. doi: 10.1021/ja806677w. Epub 2008 Oct 23.

Hydrocarboxylation of allenes with CO2 catalyzed by silyl pincer-type palladium complex.

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  • 1Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.

Abstract

Tridentate PSiP pincer-type palladium complex-catalyzed hydrocarboxylation of allenes under carbon dioxide to give synthetically useful beta,gamma-unsaturated carboxylic acids was developed. This novel CO2-fixation reaction is thought to proceed through the catalytic generation of sigma-allyl palladium species via hydropalladation of allenes, followed by its regioselective nucleophilic addition to CO2 in the presence of an appropriate reducing agent. The reaction is successfully applied to various allenes bearing functional groups such as ester, carbamate, ketone, and alkene, showing high synthetic utility of this protocol.

PMID:
18942785
[PubMed]
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