title: Fused heteroaromatic dihydrosiloles: synthesis and double-fold modification.
abstract: An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity. Fused heteroaromatic dihydrosiloles can be smoothly halogenated and then oxidized or arylated. Application of these transformations allows obtaining highly functionalized heteroaromatic structures. A gram-scale synthesis of dihydropyridinosilole has also been accomplished using reduced amounts of Ni- and Ir-catalysts.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
authors.forename: Alexey
authors.initials: A
authors.lastname: Kuznetsov
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Onishi
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Inamoto
authors.forename: Vladimir
authors.initials: V
authors.lastname: Gevorgyan
mesh_terms: D002384:Catalysis; D006860:Hydrogen Bonding; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D017646:Organosilicon Compounds; D007495:Iridium; D009532:Nickel