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Palladium-Catalyzed Conversion of Benzylic and Allylic Halides into α-Aryl and β,γ-Unsaturated Tertiary Amides by the Use of a Carbamoylsilane

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Robert F. Cunico* and Rajesh K. Pandey

Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115 rfc@marilyn.chem.niu.edu

J. Org. Chem., 2005, 70 (22), pp 9048–9050

DOI: 10.1021/jo0512406

Publication Date (Web): September 24, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Treatment of allylic and benzylic halides with N,N-dimethylcarbamoyl(trimethyl)silane in the presence of tetrakis(triphenylphosphine)palladium(0) affords tertiary amides, which arise from the replacement of the halogen by the N,N-dimethylcarbamoyl group.

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Published In Issue October 28, 2005
Received June 16, 2005

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Palladium-Catalyzed Conversion of Benzylic and Allylic Halides into α-Aryl and β,γ-Unsaturated Tertiary Amides by the Use of a Carbamoylsilane