Sila-Morita-Baylis-Hillman reaction of arylvinyl ketones: overcoming the dimerization problem.
Arylvinyl ketones, under Morita-Baylis-Hillman (MBH) reaction conditions, produce a mixture of dimerization products. We propose a solution to this problem: a sila-MBH reaction. This cascade reaction involves addition of phosphine catalyst to arylvinyl ketones, trapping of the forming beta-silylenolate with aldehyde, followed by a 1,3-Brook rearrangement to give the Si-MBH adducts in good to excellent yields.
Trofimov
Alexander
A
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Gevorgyan
Vladimir
V
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D019281:Dimerization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000447:Aldehydes; D007659:Ketones; D010720:Phosphines; D014753:Vinyl Compounds; C044646:phosphine