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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Details
Title
Studies in Acyl C-H Activation via Aryl and Alkyl to Acyl "Through Space" Migration of Palladium
Publication Details
Organic letters, Vol.11(12), pp.2591-2593
Resource Type
Journal article
Publisher
American Chemical Society (ACS)
Number of pages
3
Grant note
National Science Foundation; National Science Foundation (NSF)
Johnson Matthey, Inc.
Kawaken Fine Chemicals Co., Ltd.
Department of Science and Technology, Government of India; Department of Science & Technology (India)