Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/19730
Title: Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion
Authors: Thu, HY
Yu, WY 
Che, CM
Issue Date: 2006
Publisher: American Chemical Society
Source: Journal of the American Chemical Society, 2006, v. 128, no. 28, p. 9048-9049 How to cite?
Journal: Journal of the American Chemical Society 
Abstract: This communication describes the Pd(OAc)2-catalyzed intermolecular amidation reactions of unactivated sp2 and sp3 C−H bonds using primary amides and potassium persulfate. The substrates containing a pendent oxime or pyridine group were amidated with excellent chemo- and regioselectivities. It is noteworthy that reactive C−X bonds were well-tolerated and a variety of primary amides can be effective nucleophiles for the Pd-catalyzed C−H amidation reactions. For the reaction of unactivated sp3 C−H bonds, β-amidation of 1° sp3 C−H bonds versus 2° C−H bonds is preferred. The catalytic reaction is initiated by chelation-assisted cyclopalladation involving C−H bond activation. Preliminary mechanistic study suggested that the persulfate oxidation of primary amides should generate reactive nitrene species, which then reacted with the cyclopalladated complex.
URI: http://hdl.handle.net/10397/19730
ISSN: 0002-7863
DOI: 10.1021/ja062856v
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