Categories: C-C Bond Formation > Nitrogen-containing molecules > Nitriles
Synthesis of Vinyl Nitriles
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Recent Literature
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.
Pd(PPh3)4 catalyzes a cyanation of propargylic carbonates
with trimethylsilyl cyanide in THF under reflux to afford cyanoallenes. The use of trimethylsilyl cyanide in excess (6 equiv)
provides dicyanated products in high yields.
Y. Tsuji, M. Taniguchi, T. Yasuda, T. Kawamura, Y. Obora,
Org. Lett., 2000, 2, 2635-2637.