Synthesis
DOI: 10.1055/a-2593-4458
paper

Chitosan-Promoted Reduction of Nitroaromatics by B2(NMe2)4 under Wet Ball Milling Conditions

Yuhang Su
a   School of Materials and Packaging Engineering, Fujian Polytechnic Normal University, Fuzhou, Fujian 350300, P. R. of China
,
Jingyan Chen
b   Department of Chemistry and Materials Science, Xi’an Jiaotong-Liverpool University, Suzhou, Jiangsu 215123, P. R. of China
,
Hui Lin
a   School of Materials and Packaging Engineering, Fujian Polytechnic Normal University, Fuzhou, Fujian 350300, P. R. of China
,
Conglong Lin
a   School of Materials and Packaging Engineering, Fujian Polytechnic Normal University, Fuzhou, Fujian 350300, P. R. of China
,
Yuanzhi Lin
a   School of Materials and Packaging Engineering, Fujian Polytechnic Normal University, Fuzhou, Fujian 350300, P. R. of China
,
Xiuqiang Lu
a   School of Materials and Packaging Engineering, Fujian Polytechnic Normal University, Fuzhou, Fujian 350300, P. R. of China
c   Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
› Institutsangaben

We are grateful to National Natural Science Foundation of China (No. 51503037), Natural Science Foundation of Fujian Province (No. 2024J01968), and the Project of Fujian Provincial Science and Technology Department (No. 2024H6018, No.2024Y0030) for financial support.


Abstract

The environmentally friendly reduction of nitro compounds to their corresponding amino compounds has been a practical and challenging task. In this paper, a method has been developed for the reduction of nitroaromatics to aromatic amines by ball milling. The method uses cheap and available tetrakis(dimethylamino)diboron as the reducing agent and NaOH as the base, and the reduction reaction can be achieved by wet ball milling assisted by chitosan. A range of nitroaromatic compounds containing a variety of alkyl, halogen, polynitro, and other groups were chemoselectively reduced to the corresponding anilines in good yields. This protocol will enrich functional group transformations of nitroaromatics to amines.

Supporting Information



Publikationsverlauf

Eingereicht: 07. Februar 2025

Angenommen nach Revision: 23. April 2025

Accepted Manuscript online:
23. April 2025

Artikel online veröffentlicht:
12. Mai 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany