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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 3
BKCSDE 31(3)
March 20, 2010 

Rhodium-Catalyzed Reductive Decyanation of Nitriles Using Hydrosilane as a Reducing Agent: Scope, Mechanism and Synthetic Application
Mamoru Tobisu*, Ryo Nakamura, Yusuke Kita, Naoto Chatani*
Reductive decyanation, Carbon-carbon bond activation, Rhodium catalyst, Hydrosilane
A rhodium-catalyzed reductive cleavage reaction of carbon-cyano bonds is developed using hydrosilane as a mild reducing agent. A wide range of nitriles, including aryl, benzyl, and β-hydrogen containing alkyl cyanides are applicable to this decyanation reaction. The method is also applicable to organic synthesis, in which benzyl cyanide is used as a benzyl anion equivalent and a cyano group functions as a removable ortho-directing group.
582 - 587
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