Palladium-catalyzed carbene insertion and trapping with carbon nucleophiles.
Palladium catalysts are shown to catalyze the three-component coupling of vinyl halides, trimethylsilyldiazomethane, and stabilized carbon nucleophiles. The reaction is believed to proceed through a palladium-carbene intermediate LX(R)PdCHSiMe 3 that undergoes migration of the vinyl substituent to the electrophilic carbene center to generate an eta 3-allylpalladium intermediate. The allylpalladium intermediate is attacked by the carbon nucleophile to generate a vinylsilane product.
Devine
Sean K J
SK
Department of Chemistry, 1102 Natural Sciences, University of California, Irvine, California 92697-2025, USA.
Van Vranken
David L
DL
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003978:Diazomethane / Q000031:analogs & derivatives / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D006846:Hydrocarbons, Halogenated; D012821:Silanes; D014297:Trimethylsilyl Compounds; D014753:Vinyl Compounds; C476909:vinylsilane; C030011:carbene; D010165:Palladium; D003978:Diazomethane; D002244:Carbon; D008697:Methane; C060070:trimethylsilyldiazomethane