title: Palladium-catalyzed conjugate addition of organosiloxanes to alpha,beta-unsaturated carbonyl compounds and nitroalkenes.
abstract: The addition of aryltrialkoxysilanes to alpha,beta-unsaturated carbonyl compounds (ketones, aldehydes) and nitroalkenes in the presence of SbCl(3), TBAF, AcOH, and a catalytic amount of Pd(OAc)(2), in CH(3)CN at 60 degrees C, provides the corresponding conjugate addition products in moderate to good yields. The addition of equimolar amounts of SbCl(3) and TBAF is necessary for this reaction to proceed smoothly. The arylpalladium complex, which is generated by the transmetalation from a putative hypercoordinate silicon compound, is considered to be the catalytically active species.
authors.affiliation: Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
authors.forename: Scott E
authors.initials: SE
authors.lastname: Denmark
authors.forename: Nobuyoshi
authors.initials: N
authors.lastname: Amishiro
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D012833:Siloxanes / Q000737:chemistry*; D012997:Solvents
chemical_list: D000447:Aldehydes; D000475:Alkenes; D007202:Indicators and Reagents; D007659:Ketones; D012833:Siloxanes; D012997:Solvents; D010165:Palladium