Citation: Guo Yuanyuan, Liu Zhenwei, Zhu Mingxiang, Li Linlin, Li Jingya, Zou Dapeng, Wu Yusheng, Wu Yangjie. Copper-Promoted Dimethylthiolation of Benzamides under Assistance of 8-Aminoquinoline Group[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 724-730. doi: 10.6023/cjoc201908036 shu

Copper-Promoted Dimethylthiolation of Benzamides under Assistance of 8-Aminoquinoline Group

Guo Yuanyuan ^a ,
Liu Zhenwei ^a ,
Zhu Mingxiang ^a ,
Li Linlin ^a ,
Li Jingya ^b ,
Zou Dapeng ^a,, ,
Wu Yusheng ^b,, ,
Wu Yangjie ^a,,

a.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052
b.
Tetranov Biopharm, LLC, Zhengzhou 450052

Corresponding author: Zou Dapeng, zdp@zzu.edu.cn Wu Yusheng, yusheng.wu@tetranovglobal.com Wu Yangjie, wyj@zzu.edu.cn
Received Date: 27 August 2019
Revised Date: 5 November 2019
Available Online: 21 November 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21172200, 21702191)the National Natural Science Foundation of China 21702191the National Natural Science Foundation of China 21172200

Figures(2)

Cu(Ⅱ)-promoted dimethylthiolation of C(sp²)-H bonds using DMSO as the methylthiolation source with the assistance of an 8-aminoquinoline directing group have been developed. A number of dimethylthiolated benzamides were efficiently synthesized using CuSO₄·5H₂O as a promoter in moderate to good yields. In addition, this reaction system features facile conditions and no other oxidant additive was required.
- Dimethylthiolation,
- DMSO,
- 8-Aminoquinoline,
- Copper-promoted
1. [1]
  (a) Vernon, M. W.; Heel, R. C.; Brogden, R. N. Drugs 1991, 42, 997.
  (b) Martino, G. D.; Regina, G. L.; Coluccia, A.; Edler, M. C.; Barbera, M. C.; Brancale, A.; Wilcox, E.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2004, 47, 6120.
  (c) Martino, G. D.; Edler, M. C.; Regina, G. L.; Coluccia, A.; Barbera, M. C.; Barrow, D.; Nicholson, R. I.; Chiosis, G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 947.
2. [2]
  (a) Superchi, S.; Rosini, C. Tetrahedron: Asymmetry 1997, 8, 349.
  (b) Marom, H.; Antonov, S.; Popowski, Y.; Gozin, M. J. Org. Chem. 2011, 76, 5240.
  (c) Kowalski, P.; Mitka, K.; Ossowska, K.; Kolarska, Z. Tetrahedron 2005, 61, 1933.
  (d) Kaczorowska, K.; Kolarska, Z.; Mitka, K.; Kowalski, P. Tetrahedron 2005, 61, 8315.
3. [3]
  (a) Truce, W. E.; Breiter, J. J. J. Am. Chem. Soc. 1962, 84, 1621.
  (b) Lavanlsh, J. M. Tetrahedron Lett. 1973, 14, 3847.
  (c) Hooper, J. F.; Young, R. D.; Weller, A. S.; Willis, M. C. Chem.- Eur. J. 2013, 19, 3125.
  (d) Graham, T. H.; Liu, W.; Shen, D. M. Org. Lett. 2011, 13, 6232.
  (e) Barbero, N.; Martin, R. Org. Lett. 2012, 14, 796.
4. [4]
  (a) Eberhart, A. J.; Imbriglio, J. E.; Procter, D. J. Org. Lett. 2011, 13, 5882.
  (b) Ookubo, Y.; Wakamiya, A.; Yorimitsu, H.; Osuka, A. Chem.- Eur. J. 2012, 18, 12690.
  (c) Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599.
  (d) Modha, S. G.; Mehta, V. P.; Eycken, E. V. V. Chem. Soc. Rev. 2013, 42, 5042.
  (e) Hooper, J. F.; Young, R. D.; Pernik, I.; Weller, A. S.; Willis, M. C. Chem. Sci. 2013, 4, 1568.
  (f) Pan, F.; Wang, H.; Shen, P. X.; Zhao, J.; Shi, Z. J. Chem. Sci. 2013, 4, 1573.
  (g) Quan, Z.-J.; Lv, Y.; Jing, F. Q.; Jia, X. D.; Huo, C. D.; Wang, X. C. Adv. Synth. Catal. 2014, 356, 325.
  (h) Otsuka, S.; Fujino, D.; Murakami, K.; Yorimitsu, H.; Osuka, A. Chem.-Eur. J. 2014, 20, 13146.
5. [5]
  (a) Ram, V. J.; Agarwal, N. Tetrahedron Lett. 2001, 42, 7127.
  (b) Sugahara, T.; Murakami, K.; Yorimitsu, H.; Osuka, A. Angew. Chem., Int. Ed. 2014, 53, 9329.
  (c) Wang, X.; Tang, Y.; Long, C.; Dong, W.; Li, C.; Xu, X.; Zhao, W.; Wang, X. Org. Lett. 2018, 20, 4749.
6. [6]
  Ralf, B.; Arnim, K.; Andreas, V. A.; Hartmut, A.; Simon, D.-R.; Lothar, W.; Isolde, H.-H.; Ines, H.; Elmar, G.; Christopher Hugh, R. WO 028579, 2012.
7. [7]
  For selected examples: (a) Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
  (b) Jiang, Y.; Qin, Y.; Xie, S.; Zhang, X.; Dong, J.; Ma, D. Org. Lett. 2009, 11, 5250.
  (c) Chu, L. L.; Yue, X.; Qing, F. L. Org. Lett. 2010, 12, 1644.
  (d) Luo, F.; Pan, C. D.; Li, L. P.; Chen, F.; Cheng, J. Chem. Commun. 2011, 47, 5304.
  (e) Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237.
  (f) Jones-Mensah, E.; Magolan, J. Tetrahedron 2014, 55, 5323.
  (g) Gao, X. F.; Pan, X. J.; Gao, J.; Jiang, H. F.; Yuan, G. Q.; Li, Y. W. Org. Lett. 2015, 17, 1038.
  (h) Shen, T.; Huang, X. Q.; Liang, Y. F.; Jiao, N. Org. Lett. 2015, 17, 6186.
  (Ⅰ) Li, H. Y.; Xing, L. J.; Lou, M. M.; Wang, H.; Liu, R. H.; Wang, B. Org. Lett. 2015, 17, 1098.
  (j) Sharma, P.; Rohilla, S.; Jain, N. J. Org. Chem. 2015, 80, 4116.
  (k) Cui, X.; Liu, X.; Wang, X.; Tian, W.; Wei, D.; Huang, G. ChemistrySelect 2017, 2, 8607.
  (l) Hu, L.; Chen, X.; Yu, L.; Yu, Y.; Tan, Z.; Zhu, G.; Gui, Q. Org. Chem. Front. 2018, 5, 216.
8. [8]
  (a) Pasto, D. J. J. Am. Chem. Soc. 1962, 84, 3777.
  (b) Yamauchi, K.; Tanabe, T.; Kinoshita, M. J. Org. Chem. 1979, 44, 638.
  (c) Fry, S. E.; Pienta, N. J. J. Org. Chem. 1984, 49, 4877.
  (d) Tundo, P.; Rossi, L.; Loris, A. J. Org. Chem. 2005, 70, 2219.
  (e) Basu, B.; Paul, S.; Nanda, A. K. Green Chem. 2010, 12, 767.
9. [9]
  (a) Ranken, P. F.; McKinnie, B. G. J. Org. Chem. 1989, 54, 2985.
  (b) Stanetty, P.; Koller, H.; Mihovilovic, M. J. Org. Chem. 1992, 57, 6833.
  (c) Pratt, S. A.; Goble, M. P.; Mulvaney, M. J.; Wuts, P. G. M. Tetrahedron Lett. 2000, 41, 3559.
  (d) Fort, Y.; Rodriguez, A. L. J. Org. Chem. 2003, 68, 4918.
10. [10]
  (a) Martinek, M.; Korf, M.; Srogl, J. Chem. Commun. 2010, 46, 4387.
  (b) Saidi, O.; Marafie, J.; Ledger, A. E. W.; Liu, P. M.; Mahon, M. F.; Kociok-Köhn, G.; Whittlesey, M. K.; Frost, C. G. J. Am. Chem. Soc. 2011, 133, 19298.
  (c) Sahoo, S. K.; Banerjee, A.; Chakraborty, S.; Patel, B. K. ACS Catal. 2012, 2, 544.
  (d) Umierski, N.; Manolikakes, G. Org. Lett. 2013, 15, 4972.
  (e) Wu, Z.; Song, H.; Cui, X.; Pi, C.; Du, W.; Wu, Y. Org. Lett. 2013, 15, 1270.
  (f) Niu, B.; Xu, L.; Xie, P.; Wang, M.; Zhao, W.; Pittman, C. U.; Zhou, A. ACS Comb. Sci. 2014, 16, 454.
  (g) Corbet M.; Campo, F. D. Angew. Chem., Int. Ed. 2013, 52, 9896.
11. [11]
  For select reviews on transition-metal-catalyzed C—S bond formations, see: (a) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033.
  (b) Kondo, T.; Mitsudo, T.-A. Chem. Rev. 2000, 100, 3205.
  (c) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
  (d) Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590.
  (e) Postigo, A. RSC Adv. 2011, 1, 14. (f) Liu, W.; Zhao, X. Synthesis 2013, 2051.
12. [12]
  Peng, J.-J.; Deng, Y. Q. Chin. J. Org. Chem. 2002, 22, 71(in Chinese). doi: 10.3321/j.issn:0253-2786.2002.01.012
13. [13]
14. [14]
1. [1]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
2. [2]
  Liuyun Chen , Wenju Wang , Tairong Lu , Xuan Luo , Xinling Xie , Kelin Huang , Shanli Qin , Tongming Su , Zuzeng Qin , Hongbing Ji . Soft template-induced deep pore structure of Cu/Al₂O₃ for promoting plasma-catalyzed CO₂ hydrogenation to DME. Acta Physico-Chimica Sinica, 2025, 41(6): 100054-. doi: 10.1016/j.actphy.2025.100054
3. [3]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
4. [4]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
5. [5]
  Jianding LI , Junyang FENG , Huimin REN , Gang LI . Proton conductive properties of a Hf(Ⅳ)-based metal-organic framework built by 2,5-dibromophenyl-4,6-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1094-1100. doi: 10.11862/CJIC.20240464
6. [6]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
7. [7]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
8. [8]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
9. [9]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
10. [10]
  Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
11. [11]
  Yan Wang , Si-Meng Zhai , Peng Luo , Xi-Yan Dong , Jia-Yin Wang , Zhen Han , Shuang-Quan Zang . Vapor- and temperature-triggered reversible optical switching for multi-response Cu₈ cluster supercrystals. Chinese Chemical Letters, 2024, 35(11): 109493-. doi: 10.1016/j.cclet.2024.109493
12. [12]
  Yuan Yang , Jian Zhang , Shaomin Shuang . Promoting an All-English Teaching Approach in the Chemistry English Curriculum to Enhance Internationalization. University Chemistry, 2025, 40(5): 238-243. doi: 10.12461/PKU.DXHX202403079
13. [13]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
14. [14]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
15. [15]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
16. [16]
  Cuicui Yang , Bo Shang , Xiaohua Chen , Weiquan Tian . Understanding the Wave-Particle Duality and Quantization of Confined Particles Starting from Classic Mechanics. University Chemistry, 2025, 40(3): 408-414. doi: 10.12461/PKU.DXHX202407066
17. [17]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
18. [18]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
19. [19]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
20. [20]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(1077)
HTML views(159)

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