电化学促进硝基芳烃的脱硝基硼化和磺酰氟化反应

引用本文: 曹中艳, 徐尤智, 李梦华, 肖霄, 孔宪强, 钱德云. 电化学促进硝基芳烃的脱硝基硼化和磺酰氟化反应[J]. 大学化学, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017 shu

Citation: Zhongyan Cao, Youzhi Xu, Menghua Li, Xiao Xiao, Xianqiang Kong, Deyun Qian. Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes[J]. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017 shu

电化学促进硝基芳烃的脱硝基硼化和磺酰氟化反应

曹中艳 ^1, ,
徐尤智 ^1, ,
李梦华 ^1, ,
肖霄 ^3, ,
孔宪强 ^4, ,
钱德云 ^2,

1.
河南大学化学与分子科学学院, 河南开封 475004;
2.
云南大学药学院, 自然资源药物化学教育部重点实验室, 云南省天然产物转化与应用重点实验室, 昆明 650500;
3.
浙江工业大学长三角绿色制药协同创新中心, 杭州 310014;
4.
常州工学院化工与材料学院, 江苏常州 213032
基金项目:
国家自然科学基金(22201062, 22372015, 22202021, 22208302, 22101250)；河南大学校级教改项目(HDXJJG-2022-035)

摘要: 硝基芳烃广泛应用于有机合成中，是本科有机化学教学内容的重点之一。温和条件下脱硝基转化的高效方法十分有限。近年来，绿色电合成技术为硝基芳烃C―N键的选择性转化提供了新思路。本文结合学科前沿，选取本科生易于理解的反应实例介绍硝基芳烃脱硝基转化的最新进展，以开阔学生视野、激发学习兴趣、丰富知识储备。

关键词:

English

Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes

1.
College of Chemistry and Molecular Sciences, Henan University, Kaifeng 475004, Henan Province, China;
2.
Yunnan Key Laboratory of Research and Development for Natural Products, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education;School of Pharmacy, Yunnan University, Kunming 650500, China;
3.
Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China;
4.
School of Chemical Engineering and Materials, Changzhou Institute of Technology, Changzhou 213032, Jiangsu Province, China
Received Date: 01 July 2024
Revised Date: 02 September 2024
Available Online: 06 November 2024

Abstract: Nitroarenes are widely utilized in organic synthesis and are a key topic in undergraduate organic chemistry curricula. However, efficient methods for denitrative transformations of nitroarenes under mild conditions remain limited. In recent years, green electrochemical synthesis has emerged as a promising approach for the selective C―N bond transformations of nitroarenes. This mini-review highlights recent advances in electrochemically facilitated denitrative transformations of nitroarenes, using reaction examples that are accessible to undergraduate students. These examples aim to expand students’ understanding of denitrative processes, stimulate their interest in the field, enhance their learning experience, and enrich their knowledge base.

Key words:

1. [1]
  Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, NY, USA, 2001.Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, NY, USA, 2001.
2. [2]
  邢其毅, 裴伟伟, 徐瑞秋, 裴坚. 基础有机化学. 北京: 北京大学出版社, 2016.
3. [3]
  Kashihara, M.; Nakao, Y. Acc. Chem. Res. 2021, 54, 2928.Kashihara, M.; Nakao, Y. Acc. Chem. Res. 2021, 54, 2928.
4. [4]
  Muto, K.; Okita, T.; Yamaguchi, J. ACS Catal. 2020, 10, 9856.Muto, K.; Okita, T.; Yamaguchi, J. ACS Catal. 2020, 10, 9856.
5. [5]
  Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
6. [6]
  Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27.Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27.
7. [7]
  Ma, C.; Fang, P.; Liu, Z.; Xu, S.; Xu, K.; Cheng, X.; Lei, A.; Xu, H.; Zeng, C. C.; Mei, T.-S. Sci. Bull. 2021, 66, 2412.Ma, C.; Fang, P.; Liu, Z.; Xu, S.; Xu, K.; Cheng, X.; Lei, A.; Xu, H.; Zeng, C. C.; Mei, T.-S. Sci. Bull. 2021, 66, 2412.
8. [8]
  Liu, C.; Li, J.; Wu, N.; Cheng, X. Org. Biomol. Chem. 2021, 19, 2468.Liu, C.; Li, J.; Wu, N.; Cheng, X. Org. Biomol. Chem. 2021, 19, 2468.
9. [9]
  Du, L.; Zhang, B.; Ji, S.; Cai, H.; Zhang, H. Sci. China: Chem. 2023, 66, 534.Du, L.; Zhang, B.; Ji, S.; Cai, H.; Zhang, H. Sci. China: Chem. 2023, 66, 534.
10. [10]
  Kong, X.; Liu, Q.; Chen, Y.; Wang, W.; Chen, H.; Wang, W.; Zhang, S.; Chen, X.; Cao, Z.-Y. Green Chem. 2024, 26, 3435.Kong, X.; Liu, Q.; Chen, Y.; Wang, W.; Chen, H.; Wang, W.; Zhang, S.; Chen, X.; Cao, Z.-Y. Green Chem. 2024, 26, 3435.
11. [11]
  Hall, D. G. Boronic Acids: Preparation and Applications in Organic Synthesis Medicine and Materials, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2011.Hall, D. G. Boronic Acids: Preparation and Applications in Organic Synthesis Medicine and Materials, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2011.
12. [12]
  Lou, T. S.-B.; Willis, M. C. Nat. Rev. Chem. 2022, 6, 146.Lou, T. S.-B.; Willis, M. C. Nat. Rev. Chem. 2022, 6, 146.
13. [13]
  Kong, X.; Chen, Y.; Liu, Q.; Wang, W.; Zhang, S.; Zhang, Q.; Chen, X.; Xu, Y.-Q.; Cao, Z.-Y. Org. Lett. 2023, 25, 581.Kong, X.; Chen, Y.; Liu, Q.; Wang, W.; Zhang, S.; Zhang, Q.; Chen, X.; Xu, Y.-Q.; Cao, Z.-Y. Org. Lett. 2023, 25, 581.
14. [14]
  Kong, X.; Chen, Y.; Chen, X.; Ma, C.; Chen, M.; Wang, W.; Xu, Y.-Q.; Ni, S.-F.; Cao, Z.-Y. Nat. Commun. 2023, 14, 6933.Kong, X.; Chen, Y.; Chen, X.; Ma, C.; Chen, M.; Wang, W.; Xu, Y.-Q.; Ni, S.-F.; Cao, Z.-Y. Nat. Commun. 2023, 14, 6933.
15. [15]
  Zhang, H.; Sun, X.; Ma, C.; Li, C.; Ni, Y.; Yu, Y.; Xu, Y.-Q.; Ni, S.-F.; Cao, Z.-Y. ACS Catal. 2024, 14, 3115.Zhang, H.; Sun, X.; Ma, C.; Li, C.; Ni, Y.; Yu, Y.; Xu, Y.-Q.; Ni, S.-F.; Cao, Z.-Y. ACS Catal. 2024, 14, 3115.
16. [16]
  Fan, J.; Ye, W.; Wang, R.; Xu, L.; Wu, X. J. Electrochem. 2009, 15 (3), 260.Fan, J.; Ye, W.; Wang, R.; Xu, L.; Wu, X. J. Electrochem. 2009, 15 (3), 260.

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沈阳化工大学材料科学与工程学院沈阳 110142

电化学促进硝基芳烃的脱硝基硼化和磺酰氟化反应

English

Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes

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中国化学会秘书处

电化学促进硝基芳烃的脱硝基硼化和磺酰氟化反应

English

Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

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CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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