B2(OH)4-Mediated Reductive Transamidation of N-Acyl Benzotriazoles with Nitro Compounds En Route to Aqueous Amide Synthesis
Jin Bai, Shangzhang Li, Riqian Zhu, Yang Li and Wanfang Li*
*School of Materials and Chemistry, University of Shanghai
for Science and Technology, Shanghai 200093, P. R. China, Email: lwf
usst.edu.cn
J. Bai, S. Li, R. Zhu, Y. Li, W. Li, J. Org. Chem., 2023, 88, 3714-3723.
DOI: 10.1021/acs.joc.2c02995
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Abstract
B2(OH)4 mediates a reductive transamidation reaction between N-acyl benzotriazoles and organic nitro compounds or NaNO2 under mild conditions in H2O as solvent. N-Deuterated amides can be synthesized when conducting the reaction in D2O. A reasonable reaction mechanism involves bond metathesis between the AcBt amide and an amino boric acid intermediate.
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proposed mechanism
Key Words
amides, reduction of nitro compounds, tetrahydroxydiboron
ID: J42-Y2023
