Sodium Nitrite
Name Reactions
Recent Literature
An electrolysis of terminal alkynes into their corresponding carboxylic acids
in an undivided cell at room temperature avoids transition metal catalysis and
stoichiometric chemical oxidants. The reaction tolerates a variety of aryl,
heteroaryl, and alkyl alkynes. Sodium nitrite serves a triple role as the
electrolyte, nitryl radical precursor, and a nitrosating reagent.
Q. Feng, Y. Wang, B. Zheng, S. Huang, Org. Lett., 2023, 25,
293-297.
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.
