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: dawei.gongjlnu.edu.cn, Zhaolina1975163.com

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

DOI: 10.1021/acs.orglett.3c01529

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Abstract

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

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Key Words

reduction of azo compounds, ammonia borane

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ID: J54-Y2023