Noncatalyzed Reduction of Nitriles to Primary Amines with Ammonia Borane

Man Ding, Jiarui Chang, Jia-Xue Mao, Jie Zhang* and Xuenian Chen*

*School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China, Email: jie.zhanghtu.edu.cn, xuenian_chenzzu.edu.cn

M. Ding, J. Chang, J.-X. Mao, J. Zhang, X. Chen, J. Org. Chem., 2022, 87, 16230-16235.

DOI: 10.1021/acs.joc.2c01727

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Abstract

A wide range of nitriles were reduced to primary amines by 1.2 equiv of ammonia borane under thermal decomposition conditions without any catalyst to primary amines in very good yields. The reactions are environmentally benign with H₂ and NH₃ generated as byproducts. The reactions are also tolerant of many functional groups.

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proposed mechanism

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Key Words

reduction of nitriles, ammonia borane

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ID: J42-Y2022