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: ybkangustc.edu.cn

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

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Abstract

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.

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proposed mechanism

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Key Words

nitriles, sodium nitrite

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ID: J54-Y2016