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Categories: C-C Bond Formation > Nitrogen-containing molecules > Nitriles

Synthesis of Vinyl Nitriles

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A palladium-catalyzed cyanation of alkenyl halides using acetone cyanohydrin enables the preparation of structurally diverse alkenylic nitrile containing compounds in one step. The reaction is efficient, chemoselective, easy to perform, and tolerates a number of functional groups.
K. J. Powell, L-C. Han, P. Sharma, J. E. Moses, Org. Lett., 2014, 16, 2158-2161.


A highly stereo- and regioselective hydrocyanation of terminal alkynes provides E-configured alkenyl nitriles employing acetone cyanohydrin as a practical alternative to HCN gas. Acrylonitriles can be accessed on gram scale with broad substrate scope and functional group tolerance.
F. Ye, J. Chen, T. Ritter, J. Am. Chem. Soc., 2017, 139, 7184-7187.


A catalytic, regioselective oxidative cyanation of conjugated and nonconjugated alkenes using a homogeneous copper catalyst and Selectfluor as oxidant provides branched alkenyl nitriles that are difficult to prepare.
D.-W. Gao, E. V. Vinogradova, S. K. Nimmagadda, J. M. Medina, Y. Xiao, R. M. Suciu, B. F. Cravatt, K. M. Engle, J. Am. Chem. Soc., 2018, 140, 8069-8073.


An efficient, regioselective, and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water provides functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions. The use of the volatile and hazardous HCN can be avoided.
X. Zhang, X. Xie, Y. Liu, J. Am. Chem. Soc., 2018, 140, 7385-7389.


An efficient, regioselective, and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water provides functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions. The use of the volatile and hazardous HCN can be avoided.
X. Zhang, X. Xie, Y. Liu, J. Am. Chem. Soc., 2018, 140, 7385-7389.


Lewis-acid catalysts such as AlMe3, AlMe2Cl, and BPh3 significantly improve the efficiency of the nickel-catalyzed aryl- and alkenylcyanation of alkynes. Electron-rich cyanides, which exhibit poor reactivity in the absence of Lewis acids, readily undergo the arylcyanation reaction under the newly disclosed conditions.
Y. Nakao, A. Yada, S. Ebata, T. Hiyama, J. Am. Chem. Soc., 2007, 129, 2428-2429.


Y. Nakao, A. Yada, S. Ebata, T. Hiyama, J. Am. Chem. Soc., 2007, 129, 2428-2429.


Y. Nakao, A. Yada, S. Ebata, T. Hiyama, J. Am. Chem. Soc., 2007, 129, 2428-2429.