A transition-metal-free deacylative C(sp3)-C(sp2) bond cleavage enables a practical oxidative amination of ketones and aldehydes to nitriles using cheap and commercially abundant NaNO2 as the oxidant and the nitrogen source. Various nitriles bearing aryl, heteroaryl, alkyl, and alkenyl groups could be smoothly obtained from ketones and aldehydes in high yields.
J.-J. Ge, C.-Z. Yao, M.-M. Wang, H.-X. Zheng, Y.-B. Kang, Y. Li, Org. Lett., 2016, 18, 228-231.
Using NaNO2 as the nitrogen source and Fe(OTf)3 as a promoter at 50°C, a series of arylacetic acids provides aromatic nitriles in good yields. The reaction is compatible with a broad range of functional groups.
Z. Shen, W. Liu, X. Tian, Z. Zhao, Y.-L. Ren, Synlett, 2020, 31, 1805-1808.
A convenient and general one-step preparation of aromatic and some heterocyclic iodides in good yields includes a sequential diazotization-iodination of aromatic amines with KI, NaNO2, and p-TsOH in acetonitrile at room temperature.
E. A. Krasnokutskaya, N. I. Semenischeva, V. D. Filimonov, P. Knochel, Synthesis, 2007, 81-84.