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Synthesis of vinyl nitriles

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Allyl-nickel catalysis enables α,β-dehydrogenation of carbonyl compounds. In addition, an oxidative cycloalkenylation reaction provides access to bicycloalkenones with fused, bridged, and spirocyclic ring systems using unactivated ketone and alkene precursors.
D. Huang, S. M. Szewczyk, P. Zhang, T. R. Newhouse, J. Am. Chem. Soc., 2019, 141, 5669-5674.


A simple three-step single-pot procedure for Z-stereoselective synthesis of β-monosubstituted acrylonitriles involves olefination of aldehydes with an in situ generated α-diaminoboryl carbanion species. Various aromatic and aliphatic aldehydes were smoothly converted into the corresponding (Z)-olefin products in good yields.
T. Tomioka, Y. Takahashi, T. G. Vaughan, T. Yanase, Org. Lett., 2010, 12, 2171-2173.


An inexpensive homogeneous iron catalyst enables a direct approach to alkenyl nitriles from allylarenes or alkenes. Three C-H bond cleavages occur under the mild conditions during this process, involving the cleavage of the allyl C(sp3)-H bond as the rate-determining step.
C. Qin, N. Jiao, J. Am. Chem. Soc., 2010, 132, 15893-15895.


An α-olefination of nitriles using primary alcohols, via dehydrogenative coupling of alcohols with nitriles is catalyzed by a manganese pincer complex. The reaction runs in the absence of any additives, base, or hydrogen acceptor, liberating dihydrogen and water as the only byproducts.
S. Chakraborty, U. K. Das, Y. Ben-David, D. Milstein, J. Am. Chem. Soc., 2017, 139, 11710-11713.