Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Rhodium-Catalyzed Reductive Decyanation of Nitriles Using Hydrosilane as a Reducing Agent: Scope, Mechanism and Synthetic Application

  • Tobisu, Mamoru (Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University) ;
  • Nakamura, Ryo (Department of Applied Chemistry, Faculty of Engineering, Osaka University) ;
  • Kita, Yusuke (Department of Applied Chemistry, Faculty of Engineering, Osaka University) ;
  • Chatani, Naoto (Department of Applied Chemistry, Faculty of Engineering, Osaka University)
  • Published : 2010.03.20
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Abstract

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 $\beta$-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.

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References

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