title: Rhodium-catalyzed reductive cleavage of carbon-cyano bonds with hydrosilane: a catalytic protocol for removal of cyano groups.
abstract: The rhodium-catalyzed reductive cleavage of carbon-cyano bonds is developed using hydrosilane as a mild reducing agent. A wide range of nitriles, including aryl, benzyl, and beta-hydrogen containing alkyl cyanides are applicable to this decyanation reaction. The method can also be applied to organic synthesis; the use of benzyl cyanide as a benzyl anion equivalent and the use of a cyano group as a removable ortho-directing group are demonstrated.
authors.affiliation: Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka, Japan. tobisu@chem.eng.osaka-u.ac.jp
authors.forename: Mamoru
authors.initials: M
authors.lastname: Tobisu
authors.forename: Ryo
authors.initials: R
authors.lastname: Nakamura
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kita
authors.forename: Naoto
authors.initials: N
authors.lastname: Chatani
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D001555:Benzene Derivatives; D009570:Nitriles; D009942:Organometallic Compounds; D012821:Silanes; D012238:Rhodium