Citation: Zhang Zhenlei, Qian Peng, Zha Zhenggen. Copper-Catalyzed Aerobic Oxidative Coupling of Aromatic Sulfonyl Hydrazides with Amines:A New Access to Aromatic Sulfonamides[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1316-1322. doi: 10.6023/cjoc201903009 shu

Copper-Catalyzed Aerobic Oxidative Coupling of Aromatic Sulfonyl Hydrazides with Amines:A New Access to Aromatic Sulfonamides

School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026

Corresponding author: Zhang Zhenlei, helenken@mail.ustc.edu.cn Zha Zhenggen, zgzha@ustc.edu.cn
Received Date: 5 March 2019
Revised Date: 26 March 2019
Available Online: 19 May 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21672200, 21472177)the National Natural Science Foundation of China 21672200the National Natural Science Foundation of China 21472177

Figures(5)

A copper(Ⅱ)-catalyzed aerobic oxidative coupling of aromatic sulfonyl hydrazides with amines for the synthesis of aromatic sulfonamides was described. In contrast to previously described methods, this reaction employs copper/O₂ as the catalytic system, and generates N₂ as the only byproduct, which provides an environmentally benign synthetic route for aromatic sulfonamides.
- copper catalysis,
- sulfonyl hydrazide,
- sulfonamide
1. [1]
  For recent reviews, see:
  (a) Studer, A.; Curran, D. P. Angew. Chem. Int. Ed. 2016, 55, 58.
  (b) Yan, M.; Lo, J. C.; J. Edwards, T.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 12692.
  (c) Kärkäs, M. D. ACS Catal. 2017, 7, 4999.
  (d) Jiang, Y.; Xu, K.; Zeng, C. C. Chem. Rev. 2018, 118, 4485.
2. [2]
  For recent reviews, see:
  (a) McCann, S. D.; Stahl, S. S. Acc. Chem. Res. 2015, 48, 1756.
  (b) Shimkin, K. W.; Watson, B. D. A. J. Org. Chem. 2015, 11, 2278.
  (c) Guo, X.-X.; Gu, D.-W.; Wu, Z.; Zhang, W. B. Chem. Rev. 2015, 115, 1622.
  (d) Liang, Y.-F.; Jiao, N. Acc. Chem. Res. 2017, 50, 1640.
3. [3]
  For recent reviews, see:
  (a) Zhu, X.; Chiba, S. Chem. Soc. Rev. 2016, 45, 4504.
  (b) Tang, X. D.; Wu, W. Q.; Zeng, W.; Jiang, H. F. Acc. Chem. Res. 2018, 51, 1092.
4. [4]
  For recent examples, see:
  (a) Lee, C.; Wang, X.; Jang, H.-Y. Org. Lett. 2015, 17, 1130,
  (b) Chen, C.-Y.; Tang, G.; He, F.; Wang, Z.; Jing, H.; Faessler, R. Org. Lett. 2016, 18, 1690.
  (c) Ryan, M. C.; Martinelli, J. R.; Stahl, S. S. J. Am. Chem. Soc. 2018, 140, 9074.
5. [5]
  (a) Talley, J. J.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Rogers, R. S.; Shaffer, A. F.; Zhang, Y. Y.; Zweifel, B. S.; Seibert, K. J. Med. Chem. 2000, 43, 775
  (b) Shen, C.-H.; Wang, Y.-F.; Kovalevsky, A. Y.; Harrison, R. W.; Weber, I. T. FEBS J. 2010, 277, 3699.
  (c) McCormack, P. L. Durgs 2011, 71, 2457.
6. [6]
  (a) De Boer, T. J.; Backer, H. J. Org. Synth. 1954, 34, 96.
  (b) Harmata, M.; Zheng, P.; Huang, C.; Gomes, M. G.; Ying, W.; Ranyanil, K.-O.; Balan, G.; Calkins, N. L. J. Org. Chem. 2006, 72, 683.
7. [7]
  (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
  (b) Burton, G.; Cao, P.; Li, G.; Rivero, R. Org. Lett. 2003, 5, 4373.
  (c) Rosen, B. R.; Ruble, J. C.; Beauchamp, T. J.; Navarro, A. Org. Lett. 2011, 13, 2564.
  (d) Baffoe, J.; Hoe, M. Y.; Toure, B. B. Org. Lett. 2010, 12, 1532.
  (e) Audisio, D.; Messaoudi, S.; Peyrat, J. F.; Brion, J. D.; Alami, M. J. Org. Chem. 2011, 76, 4995.
8. [8]
  (a) Shekhar, S.; Dunn, T. B.; Kotecki, B. J.; Montavon, D. K.; Cullen, S. C. J. Org. Chem. 2011, 76, 4552.
  (b) Moon, S.-Y.; Nam, J.; Rathwell, K.; Kim, W.-S. Org. Lett. 2014, 16, 338.
9. [9]
  (a) Shi, F.; Tse, M. K.; Zhou, S.; Pohl, M.-M.; Radnik, J.; Hubner, S.; Jä hnisch, K.; Brückner, A.; Beller, M. J. Am. Chem. Soc. 2009, 131, 1775.
  (b) Zhu, M.; Fujita, K.; Yamaguchi, R. Org. Lett. 2010, 12, 1336.
  (c) Cui, X.; Shi, F.; Zhang, Y.; Deng, Y. Tetrahedron Lett. 2010, 51, 2048.
  (d) Watson, A. J. A.; Maxwell, A. C.; Williams, J. M. J. J. Org. Chem. 2011, 76, 2328.
  (e) Shekhar, S.; Dunn, T. B.; Kotecki, B. J.; Montavon, D. K.; Cullen, S. C. J. Org. Chem. 2011, 76, 4552.
10. [10]
  Tang, X. D.; Huang, L. B.; Qi, C. R.; Wu, X.; Wu, W. Q.; Jiang, H. F. Chem. Commun. 2013, 49, 6102. doi: 10.1039/c3cc41249k
11. [11]
  Huang, X.; Wang, J. C.; Ni, Z. Q.; Wang, S. C.; Pan, Y. J. Chem. Commun. 2014, 50, 4582. doi: 10.1039/C4CC01353K
12. [12]
  Zhu, M.; Wei, W.; Liu, C. L.; Yang, D. S.; Wen, J. W.; You, J. M.; Wang, H. Adv. Synth. Catal. 2015, 357, 987. doi: 10.1002/adsc.v357.5
13. [13]
  Pan, X. J.; Gao, J.; Liu, J.; Lai, J. Y.; Jiang, H. F.; Yuan, G. Q. Green Chem. 2015, 17, 1400. doi: 10.1039/C4GC02115K
14. [14]
  Yang, K.; Ke, M. L.; Lin, Y. G.; Song, Q. L. Green Chem. 2015, 17, 1395. doi: 10.1039/C4GC02236J
15. [15]
  (a) Zhu, H.; Shen, Y.; Deng, Q.; Tu, T. Chem. Commun. 2015, 51, 16573.
  (b) Zhang, F.; Zheng, D.; Lai, L.; Cheng, J.; Sun, J.; Wu, J. Org. Lett. 2018, 20, 1167.
16. [16]
  (a) Yotphan, S.; Sumunnee, L.; Beukeaw, D.; Buathongjan, C.; Reutrakul, V. Org. Biomol. Chem. 2016, 14, 590.
  (b) Feng, J.-B.; Wu, X.-F. Org. Biomol. Chem. 2016, 14, 6951.
  (c) Parumala, S. K. R.; Peddinti, R. K. Tetrahedron Lett. 2016, 57, 1232.
  (d) Zhu, M.; Wei, W.; Yang, D.; Cui, H.; Wang, L.; Meng, G.; Wang, H. Org. Biomol. Chem. 2017, 15, 4789.
  (e) Yu, H.; Zhang, Y. Chin. J. Chem. 2016, 34, 359.
17. [17]
  (a) Powell, D. A.; Fan, H. J. Org. Chem. 2010, 75, 2726.
  (b) Li, W.; Beller, M.; Wu, X.-F. Chem. Commun. 2014, 50, 9513.
  (c) Ji, J.; Liu, Z.; Liu, P.; Sun, P. P. Org. Biomol. Chem. 2016, 14, 7018.
  (d) Zhang, W.; Luo, M. Chem. Commun. 2016, 52, 2980.
  (e) Shyam, P. K.; Jang, H.-Y. J. Org. Chem. 2017, 82, 1761.
18. [18]
  (a) Yang, F.-L.; Tian, S.-K. Tetrahedron Lett. 2017, 58, 487.
  (b) Chung, S.; Kim, J. Tetrahedron Lett. 2019, 60, 792.
19. [19]
  (a) Li, L.; Li, Z.-L.; Gu, Q.-S.; Wang, N.; Liu, X.-Y. Sci. Adv. 2017, 3, e1701487.
  (b) Li, X.-T.; Gu, Q.-S.; Dong, X.-Y.; Meng, X.; Liu, X.-Y. Angew. Chem. 2018, 57, 7668.
  (c) Lin, J.-S.; Li, T.-T.; Liu, J.-R.; Jiao, G.-Y.; Gu, Q.-S.; Cheng, J.-T.; Guo, Y.-L.; Hong, X.; Liu, X.-Y. J. Am. Chem. Soc. 2019, 141, 1074.
20. [20]
  Intermediate 5 has been proposed by some previous reports, see:
  (a) Yang, F.-L.; Tian, S.-K. Tetrahedron Lett. 2017, 58, 487.
  (b) Li, X. Q.; Xu, X. S.; Hu, P. Z.; Xiao, X. Q.; Zhou, C. J. Org. Chem. 2013, 78, 7343.
  (c) Yang, F.-L.; Tian, S.-K. Angew. Chem., Int. Ed. 2013, 52, 4929.
21. [21]
  The sulfonyl radical could be initiated by O₂, for selected examples, see:
  (a) Lu, Q.; Zhang, J.; Zhao, G.; Qi, Y.; Wang, H.; Lei, A. J. Am. Chem. Soc. 2013, 135, 11481.
  (b) Shen, T.; Yuan, Y.; Song, S.; Jiao, N. Chem. Commun. 2014, 50, 4115.
22. [22]
  Alonso, E.; Ramón, D. J.; Yus, M. Tetrahedron 1997, 53, 14355. doi: 10.1016/S0040-4020(97)00920-4
1. [1]
  Jinshuai Zheng , Junfeng Niu , Crispin Halsall , Yadi Guo , Peng Zhang , Linke Ge . New insights into transformation mechanisms for sulfate and chlorine radical-mediated degradation of sulfonamide and fluoroquinolone antibiotics. Chinese Chemical Letters, 2025, 36(5): 110202-. doi: 10.1016/j.cclet.2024.110202
2. [2]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
3. [3]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
4. [4]
  Cailing Wu , Shaojie Wu , Qifei Huang , Kai Sun , Xianqiang Huang , Jianji Wang , Bing Yu . Potassium-modified carbon nitride photocatalyzed-aminoacylation of N-sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110250-. doi: 10.1016/j.cclet.2024.110250
5. [5]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
6. [6]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
7. [7]
  Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
8. [8]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
9. [9]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
10. [10]
  Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
11. [11]
  Shaonan Tian , Yu Zhang , Qing Zeng , Junyu Zhong , Hui Liu , Lin Xu , Jun Yang . Core-shell gold-copper nanoparticles: Evolution of copper shells on gold cores at different gold/copper precursor ratios. Chinese Journal of Structural Chemistry, 2023, 42(11): 100160-100160. doi: 10.1016/j.cjsc.2023.100160
12. [12]
  Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
13. [13]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
14. [14]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
15. [15]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
16. [16]
  Guoliang Liu , Zhiqiang Liu , Anmin Zheng . Modulation of zeolite surface realizes dynamic copper species redispersion. Chinese Journal of Structural Chemistry, 2024, 43(6): 100308-100308. doi: 10.1016/j.cjsc.2024.100308
17. [17]
  Luyao Lu , Chen Zhu , Fei Li , Pu Wang , Xi Kang , Yong Pei , Manzhou Zhu . Ligand effects on geometric structures and catalytic activities of atomically precise copper nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(10): 100411-100411. doi: 10.1016/j.cjsc.2024.100411
18. [18]
  Rui TIAN , Duo LI , Yuan REN , Jiamin CHAI , Xuehua SUN , Haoyu LI , Yuecheng ZHANG . Dual-ligand-modified copper nanoclusters: Synthesis and application in ornidazole detection. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1245-1255. doi: 10.11862/CJIC.20240389
19. [19]
  Lei Zhang , Chenyang Kou , Kun Ni , Yiwen Chen , Tongchuan Zhang , Baoliang Zhang . Microenvironment regulation of copper sites by chelating hydrophobic polymer for electrosynthesis of ethylene. Chinese Chemical Letters, 2025, 36(6): 110836-. doi: 10.1016/j.cclet.2025.110836
20. [20]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(693)
HTML views(62)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142