Rhodium-catalyzed reductive cleavage of carbon-cyano bonds with hydrosilane: a catalytic protocol for removal of cyano groups.
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.
Tobisu
Mamoru
M
Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka, Japan. tobisu@chem.eng.osaka-u.ac.jp
Nakamura
Ryo
R
Kita
Yusuke
Y
Chatani
Naoto
N
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
D000473:Alkanes; D001555:Benzene Derivatives; D009570:Nitriles; D009942:Organometallic Compounds; D012821:Silanes; D012238:Rhodium