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Ni(II)-Catalyzed Transfer Hydrogenation of Azoarenes with NH3BH3

Dawei Gong*, Degong Kong, Yufei Li, Caiyu Gao and Lina Zhao*

*College of Chemistry, Jilin Normal University, Changchun 130103, P. R. China, Email:,

D. Gong, D. Kong, Y. Li, C. Gao, L. Zhao, Org. Lett., 2023, 25, 4168-4172.

DOI: 10.1021/acs.orglett.3c01529


Nickel catalyzes a semihydrogenation of azoarenes with NH3BH3 to provide hydrazoarenes with good functional group tolerance and a high turnover frequency at room temperature. Results of control and deuterium-labeling experiments indicate that the ethanol hydroxyl and BH3 groups each donated one hydrogen to this transfer hydrogenation, and the main byproducts were B(OEt)3 and H2.

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proposed mechanism

Key Words

reduction of azo compounds, ammonia borane

ID: J54-Y2023