One-pot, catalytic regio- and stereoselective preparation of (Z)-β-chalcogenyl acrylamides

ORGN 85

Daniel J. Knapton and Tara Y. Meyer. Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15213
Pd(PPh3)4 is found to catalytically assemble sulfenamide, aliphatic alkyne, carbon monoxide and diphenyl diselenide or diphenyl disulfide regio- and stereoselectively in a single pot reaction to produce either (Z)-β-selenyl acrylamide or (Z)-β-sulfenyl acrylamide. The reactions proceed in moderate to good yields (60 - 80%) and tolerate a variety of different and sensitive functional groups on both the nitrogen of the sulfenamide and the alkyne.

 

New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004