title: A palladium-catalyzed regio- and stereoselective four-component coupling reaction.
abstract: Pd(PPh(3))(4) catalytically assembles sulfenamide, alkyne, carbon monoxide, and diphenyl diselenide regio- and stereoselectively in a one-pot four-component coupling reaction to yield (Z)-beta-selenyl acrylamides. The reaction proceeds in good to excellent yields (60-95%) and is tolerant of a range of functional groups on both the nitrogen of the sulfenamide and the alkyne. Moderate selectivities ranging from 4:1 to 7:1 beta-selenyl to beta-sulfenyl acrylamide have been observed despite the initial concentration of 2:1 selenium to sulfur in the reaction. The chalcogeno selectivity was found to depend directly on CO pressure; increased pressure decreased selectivity for selenium over sulfur.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Knapton
authors.forename: Tara Y
authors.initials: TY
authors.lastname: Meyer