Organic Chemistry Portal



Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp3)-C(sp2) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes

Jing-Jie Ge, Chuan-Zhi Yao, Mei-Mei Wang, Hong-Xing Zheng, Yan-Biao Kang* and Yadong Li

*Center of Advanced Nanocatalysis, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China, Email:

J.-J. Ge, C.-Z. Yao, M.-M. Wang, H.-X. Zheng, Y.-B. Kang, Y. Li, Org. Lett., 2016, 18, 228-231.

DOI: 10.1021/acs.orglett.5b03367

see article for more reactions


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.

see article for more examples

proposed mechanism

Key Words

nitriles, sodium nitrite

ID: J54-Y2016