Room temperature palladium-catalyzed intramolecular hydroaminations of unactivated alkenes

ORGN 207

Brian M. Cochran, brianoi@u.washington.edu and Forrest E. Michael, michael@chem.washington.edu. Department of Chemistry, University of Washington, Box 351700, Seattle, WA 98195
The addition of an N-H bond across an olefin (hydroamination) is a powerful method to form nitrogen-carbon bonds. A mild, functional group tolerant method for the intramolecular hydroamination of unactivated alkenes will be reported. The tridentate ligand on palladium catalyst 1 inhibits β-hydride elimination leading to the desired transformation. The reaction can be performed at room temperature allowing the formation of five- and six-membered rings. These products contain synthetically useful nitrogen protecting groups and additional functional groups within the ring backbone.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006