Synlett 2009(19): 3135-3138  
DOI: 10.1055/s-0029-1218293
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Intermolecular Hydroamination of Vinyl Ethers

Nirmal K. Pahadi*, Jon A. Tunge*
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA
Fax: +1(785)8645396; e-Mail: tunge@ku.edu;
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Publikationsverlauf

Received 30 July 2009
Publikationsdatum:
21. Oktober 2009 (online)

Abstract

This manuscript details the development of a palladium-catalyzed hydroamination of vinyl ethers. It is proposed that palladium catalyzes the hydroamination via Brønsted base catalysis, where palladium is protonated by the relatively acidic sulfonamide to generate a palladium hydride as well as the active anionic sulfonamide nucleophile. Thus, this process is distinct from known palladium-catalyzed hydroaminations of styrene derivatives that utilize less acidic amines.