Palladium-catalyzed conjugate addition of organosiloxanes to alpha,beta-unsaturated carbonyl compounds and nitroalkenes.
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.
Denmark
Scott E
SE
Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Amishiro
Nobuyoshi
N
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
D000447:Aldehydes; D000475:Alkenes; D007202:Indicators and Reagents; D007659:Ketones; D012833:Siloxanes; D012997:Solvents; D010165:Palladium