title: Palladium-catalyzed direct C-H silylation and germanylation of benzamides and carboxamides.
abstract: A palladium-catalyzed regioselective activation of C(sp(2))-H and C(sp(3))-H bonds of benzamides and carboxamides, followed by coupling with disilanes to afford organosilanes in moderate to high yields, with the aid of 8-aminoquinoline as a directing group, is reported. Catalytic C(sp(2))-H germanylation of benzamides also proceeds under the same palladium catalysis. The reaction tolerates a wide variety of functional groups and is scalable without yield reduction. The bidentate directing group is readily removed and recovered by the reaction with a hydrazine, with concominant generation of an acyl hydrazide.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Kyalo Stephen
authors.initials: KS
authors.lastname: Kanyiva
authors.forename: Yoichiro
authors.initials: Y
authors.lastname: Kuninobu
authors.forename: Motomu
authors.initials: M
authors.lastname: Kanai
mesh_terms: D000577:Amides / Q000737:chemistry*; D000634:Aminoquinolines / Q000737:chemistry; D001549:Benzamides / Q000737:chemistry*; D002384:Catalysis; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D000634:Aminoquinolines; D001549:Benzamides; D006834:Hydrazines; D012821:Silanes; D010165:Palladium; C080436:8-aminoquinoline