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Rhodium-Catalyzed Reductive Cleavage of Carbon-Cyano Bonds with Hydrosilane: A Catalytic Protocol for Removal of Cyano Groups

Mamoru Tobisu*, Ryo Nakamura, Yusuke Kita and Naoto Chatani*

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, Japan, Email: tobisuchem.eng.osaka-u.ac.jp, chatanichem.eng.osaka-u.ac.jp

M. Tobisu, R. Nakamura, Y. Kita, N. Chatani, J. Am. Chem. Soc., 2008, 131, 3174-3175.

DOI: 10.1021/ja810142v


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Abstract

A rhodium-catalyzed reductive cleavage of carbon-cyano bonds using hydrosilane as a mild reducing agent allows the decyanation of a wide range of nitriles, including aryl, benzyl, and β-hydrogen containing alkyl cyanides. 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.


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Key Words

decyanations, silanes


ID: J48-Y2009-0770