Transition-metal-catalyzed chemoselective methylenation of dicarbonyl substrates.
Rhodium- and copper-catalyzed methylenation reactions with trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol were used to react chemoselectively with aldehydes, alkoxymethylketones, and trifluoromethylketones in substrates also containing a less reactive carbonyl group. Terminal alkenes were obtained in high yields, and no protecting group was necessary in the methylenation process.
Lebel
Hélène
H
Département de Chimie, Université de Montréal, Pavillon Roger Gaudry, 2900 Boul. Edouard-Montpetit, Montréal, Québec, Canada H3T 1J4. helene.lebel@umontreal.ca
Davi
Michaël
M
Stokłosa
Grzegorz T
GT
D019840:2-Propanol / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003978:Diazomethane / Q000031:analogs & derivatives* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008745:Methylation; D008956:Models, Chemical; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D028561:Transition Elements / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000447:Aldehydes; D007659:Ketones; D009943:Organophosphorus Compounds; D028561:Transition Elements; D014297:Trimethylsilyl Compounds; C061896:triphenylphosphine; D003978:Diazomethane; D003300:Copper; D012238:Rhodium; D019840:2-Propanol; C060070:trimethylsilyldiazomethane