title: Palladium-catalyzed regiocontrolled alpha-arylation of trimethylsilyl enol ethers with aryl halides.
abstract: Inter- and intramolecular arylations of trimethylsilyl enol ethers with aryl halides are accomplished regiospecifically in the presence of a palladium catalyst and tributyltin fluoride in refluxing benzene or toluene. The optimal catalyst system called for the use of Pd2(dba)3 and tri-tert-butylphosphine in ca. 1:2 ratio. Aryl iodides, bromides, and chlorides are all effective arylation partners in this reaction. [reaction: see text]
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Iwama
authors.forename: Viresh H
authors.initials: VH
authors.lastname: Rawal
mesh_terms: D001554:Benzene / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D006219:Halogens / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D014050:Toluene / Q000737:chemistry; D014220:Trialkyltin Compounds; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis*
chemical_list: D001965:Bromides; D002712:Chlorides; D006219:Halogens; D007454:Iodides; D014220:Trialkyltin Compounds; D014297:Trimethylsilyl Compounds; D014050:Toluene; C011559:tributyltin; D010165:Palladium; D001554:Benzene