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Studies in Acyl C-H Activation via Aryl and Alkyl to Acyl "Through Space" Migration of Palladium
Journal article   Peer reviewed

Studies in Acyl C-H Activation via Aryl and Alkyl to Acyl "Through Space" Migration of Palladium

Tanay Kesharwani, Akhilesh K. Verma, Daniel Emrich, Jeffrey A. Ward and Richard C. Larock
Organic letters, Vol.11(12), pp.2591-2593
06/18/2009
PMID: 19445501
Web of Science ID: WOS:000266930900029

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Abstract

Examples of the 1,4-migration of a palladium moiety in aryl- and alkylpalladium intermediates to the acyl position of an aldehyde or formamide have been observed. The resulting acylpalladium intermediate can undergo ester or carbamate formation by reaction with an alcohol; decarbonylation, followed by beta hydride elimination to an alkene; reaction with an organomercurial to form an ester; or alkene insertion. Deuterium-labeling studies have been used to confirm the palladium migration mechanism.

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