Categories: C-H Bond Formation >
Decyanations
Recent Literature
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.
M. Tobisu, R. Nakamura, Y. Kita, N. Chatani, J. Am. Chem. Soc., 2008,
131, 3174-3175.
Single-electron-transfer conditions using Na/15-crown-5/H2O enable
a reductive cleavage of unactivated carbon-cyano bonds in aliphatic nitriles.
Compared with the Na/NH3 electride system generated under traditional
Birch conditions, this ammonia-free electride system is more practical and
features better reactivity and chemoselectivity.
Y. Ding, S. Luo, L. Ma, J. An, J. Org. Chem., 2019, 84,
15827-15833.
The use of 1,3-dimethylimidazol-2-ylidene borane (diMeImd-BH3)
enables a decyanation of secondary aliphatic nitriles and a 2-fold decyanation
of malononitriles leading to alkanes.
T. Kawamoto, K. Oritani, A. Kawabata, T. Morioka, H. Matsubara, A. Kamimura, J. Org. Chem., 2020, 85,
6137-6142.