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Palladium-Catalyzed Diamination of Unactivated Alkenes Using N-Fluorobenzenesulfonimide as Source of Electrophilic Nitrogen

Paul A. Sibbald and Forrest E. Michael*

*Department of Chemistry, University of Washington, Box 351700, Seattle, Washington 98195-1700, Email: michaelchem.washington.edu

P. A. Sibbald, F. E. Michael, Org. Lett., 2009, 11, 1147-1149.

DOI: 10.1021/ol9000087 (free Supporting Information)


Abstract

A remarkable Pd-catalyzed diamination of unactivated alkenes using N-fluorobenzenesulfonimide (NFBS) as an aminating reagent is described. The reaction incorporates one nitrogen donor from the substrate and the other from the NFBS, thereby generating cyclic diamine derivatives in a single step. The products are differentially protected at both nitrogens, allowing for maximal synthetic flexibility.

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proposed mechanism



Key Words

pyrrolidines, 1,2-diamination


ID: J54-Y2009-0720