Citation: Cen Jinghe, Yang Kai, Li Jianxiao, Li Can, Yang Shaorong. Direct 3-Arylsulfenylation of Indoles with Thiols in Basic Ionic Liquid[J]. Chinese Journal of Organic Chemistry, ;2017, 37(12): 3213-3219. doi: 10.6023/cjoc201707005 shu

Direct 3-Arylsulfenylation of Indoles with Thiols in Basic Ionic Liquid

  • Corresponding author: Cen Jinghe,  Yang Kai,  Li Jianxiao, cejxli@scut.edu.cn Yang Shaorong, lisryang@scut.edu.cn
  • Received Date: 5 July 2017
    Revised Date: 16 August 2017
    Available Online: 18 December 2017

    Fund Project: the National Natural Science Foundation of China 21502055the China Postdoctoral Science Foundation 2016T90779the National Natural Science Foundation of China 21502055Project supported by the National Natural Science Foundation of China (Nos. 21502055, 21642005), the Fundamental Research Funds for the Central Universities (No. 2015ZM150) and the China Postdoctoral Science Foundation (No. 2016T90779)the Fundamental Research Funds for the Central Universities 2015ZM150

  • An efficient and convenient transition metal-free procedure for the synthesis of 3-sulfenylindoles derivatives in moderate to good yields from readily available indoles and thiols in basic ionic liquid has been developed. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. This sulfenylation process provides a novel route for directly accessing 3-sulfenylindoles in good to excellent yields and good functional group tolerance with high atom efficiency. Notably, the current methodology could also be conveniently applied to the synthesis of thioarylated naturally occurring biologically active frameworks.
  • 加载中
    1. [1]

      (a) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
      (b) Pan, X.; Xia, H.; Wu, J. Org. Chem. Front. 2016, 3, 1163.

    2. [2]

    3. [3]

      Bierbeek, A. V.; Gingras, M. Tetrahedron Lett. 1998, 39, 6283.  doi: 10.1016/S0040-4039(98)01327-6

    4. [4]

      (a) Qiao, Z.; Jiang, X. Org. Lett. 2016‚ 18‚ 1550.
      (b) Jiang, Y.; Liang, G.; Zhang, C.; Loh, T.-P. Eur. J. Org. Chem. 2016, 3326.

    5. [5]

      (a) Taniguchi, N. J. Org. Chem. 2004, 69, 6904.
      (b) Wang, Y.; Zhang, X.; Liu, H.; Chen, H.; Huang, D. Org. Chem. Front. 2017, 4, 31.

    6. [6]

      (a) Ravi, C.; Reddy, N. N. K.; Venkatanarayana, P.; Samanta, S.; Adimurthy, S. J. Org. Chem. 2016, 81, 9964.
      (b) Matheis, C.; Bayarmagnai, B.; Goossen, L. J. Org. Chem. Front. 2016, 3, 949.
      (c) Wen, L.-R.; Shen, Q.-Y.; Guo, W.-S.; Li, M. Org. Chem. Front. 2016, 3, 870.

    7. [7]

      (a) Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880.
      (b) Fu, R.; Hao, W.-J.; Wu, Y.-N.; Wang, N.-N.; Tu, S.-J.; Li, G.; Jiang, B. Org. Chem. Front. 2016, 3, 1452.

    8. [8]

      (a) Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem. 2009, 74, 3189.
      (b) Xi, Y.; Dong, B.; McClain, E. J.; Wang, Q.; Gregg, T. L.; Akhmedov, N. G.; Petersen, J. L.; Shi, X. Angew. Chem., Int. Ed. 2014, 53, 4657.
      (c) Xiong, H.-Y.; Pannecoucke, X.; Besset, T. Org. Chem. Front. 2016, 3, 620.

    9. [9]

      (a) Yang, F.-L.; Tian, S.-K. Angew. Chem., Int. Ed. 2013, 52, 4929.
      (b) Yuan, J.; Liu, C.; Lei, A. Org. Chem. Front. 2015, 2, 677.
      (c) Yang, F.-L.; Gui, Y.; Yu, B.-K.; Jin, Y-X.; Tian, S.-K. Adv. Synth. Catal. 2016, 358, 3368.

    10. [10]

      Funk, C. D. Nat. Rev. Drug Discovery 2005, 4, 664.  doi: 10.1038/nrd1796

    11. [11]

      (a) Ge, W.; Wei, Y. Green Chem. 2012, 14, 2066.
      (b) Azeredo, J. B.; Godoi, M.; Martins, G. M.; Silveira, C. C.; Braga, A. L. J. Org. Chem. 2014, 79, 4125.
      (c) Xiao, F.; Xie, H.; Liu, S.; Deng, G.-J. Adv. Synth. Catal. 2014, 356, 364.

    12. [12]

      (a) Zou, L.-H.; Reball, J.; Mottweiler, J.; Bolm, C. Chem. Commun. 2012, 48, 11307.
      (b) Gao, Z.; Zhu, X.; Zhang, R. RSC Adv. 2014, 4, 19891.

    13. [13]

      (a) Prasad, C. D.; Balkrishna, S. J.; Kumar, A.; Bhakuni, B. S.; Shrimali, K.; Biswas, S.; Kumar, S. J. Org. Chem. 2013, 78, 1434.
      (b) Rao, H.; Wang, P.; Wang, J.; Li, Z.; Sun, X.; Cao, S. RSC Adv. 2014, 4, 49165.

    14. [14]

      (a) Li, X.; Xu, Y.; Wu, W.; Jiang, C.; Qi, C.; Jiang, H. Chem.-Eur. J. 2014, 20, 7911.
      (b) Xu, Y.; Tang, X.; Hu, W.; Wu, W.; Jiang, H. Green Chem. 2014, 16, 3720.
      (c) Gao, Y.; Gao, Y.; Tang, X.; Peng, J.; Hu, M.; Wu, W.; Jiang, H. Org. Lett. 2016, 18, 1158.

    15. [15]

    16. [16]

      (a) Li, J.; Li, C.; Yang, S.; An, Y.; Wu, W.; Jiang, H. J. Org. Chem. 2016, 81, 2875.
      (b) Li, J.; Li, C.; Yang, S.; An, Y.; Wu, W.; Jiang, H. J. Org. Chem. 2016, 81, 7771.
      (c) Li, J.; Hu, W.; Li, C.; Yang, S.; Wu, W.; Jiang, H. Org. Chem. Front. 2017, 4, 373.

    17. [17]

      Dou, H.; Gao, S.; Fu, Z.; Liu, S. Chin. J. Org. Chem. 2011, 31, 1056(in Chinese).
       

    18. [18]

      Sang, P.; Chen, Z.; Zou, J.; Zhang, Y. Green Chem. 2013, 15, 2096.  doi: 10.1039/c3gc40724a

    19. [19]

      Huang, D.; Chen, J.; Dan, W.; Ding, J.; Liu, M.; Wu, H. Adv. Synth. Catal. 2012, 354, 2123.  doi: 10.1002/adsc.v354.11/12

    20. [20]

      Tudge, M.; Tamiya, M.; Savarin, C.; Humphrey, G. R. Org. Lett. 2006, 8, 565.  doi: 10.1021/ol052615c

    21. [21]

      Guo, Y.-J.; Tang, R.-Y.; Li, J.-H.; Zhong, P.; Zhang, X.-G. Adv. Synth. Catal. 2009, 351, 2615.  doi: 10.1002/adsc.v351:16

  • 加载中
    1. [1]

      Yajun Hou ,  Jinxin Liu ,  Tao Chen ,  Yi Zhang ,  Lei Zhou . Sonogashira coupling reaction in ionic liquids: a detailed exploration of experiment 4.4D in the “101 Plan” synthetic chemistry curriculum. University Chemistry, 2026, 41(6): 136-144. doi: 10.12461/PKU.DXHX202510101

    2. [2]

      Yameen Ahmed , Xiangxiang Feng , Yuanji Gao , Yang Ding , Caoyu Long , Mustafa Haider , Hengyue Li , Zhuan Li , Shicheng Huang , Makhsud I. Saidaminov , Junliang Yang . Interface Modification by Ionic Liquid for Efficient and Stable FAPbI3 Perovskite Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(6): 2303057-0. doi: 10.3866/PKU.WHXB202303057

    3. [3]

      Yunhao Zhang ,  Yinuo Wang ,  Siran Wang ,  Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083

    4. [4]

      Fen Tan ,  Cong Xiong ,  Yu-Xuan Ni ,  Zhihan Zhang ,  Ke Gao ,  Wen-Jing Xiao ,  Liang-Qiu Lu . Carbene chemistry teaching integrated with cutting-edge single-atom skeletal editing of indoles: a case study in organic chemistry education under the “101 Plan”. University Chemistry, 2026, 41(6): 53-59. doi: 10.12461/PKU.DXHX202506066

    5. [5]

      Hua Yu , Dingdu Chen , Xuan Wang , Lijun Yang , Geming Wang , Pu Hu . MOF-encapsulated phosphorus/nitrogen ionic liquid as a multifunctional flame-retardant additive for high-safety lithium-ion batteries. Acta Physico-Chimica Sinica, 2026, 42(7): 100201-0. doi: 10.1016/j.actphy.2025.100201

    6. [6]

      Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO2 Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040

    7. [7]

      Ting YANG , Jia AN , Jinyu ZHANG , Ruonan FAN , Rong YAN , Xiaoxia JING , Panpan CHANG , Wei YAN . Synergistic enhancement of ion migration and sulfur conversion kinetics in lithium-sulfur batteries by CeO2/g-C3N4. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 519-530. doi: 10.11862/CJIC.20250274

    8. [8]

      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

    9. [9]

      Qiaorong RU . Synthesis and characterization of tripyridine functionalized polyionic liquid luminescent materials. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 111-119. doi: 10.11862/CJIC.20250121

    10. [10]

      Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020

    11. [11]

      Tao Wang , Qin Dong , Cunpu Li , Zidong Wei . Sulfur Cathode Electrocatalysis in Lithium-Sulfur Batteries: A Comprehensive Understanding. Acta Physico-Chimica Sinica, 2024, 40(2): 2303061-0. doi: 10.3866/PKU.WHXB202303061

    12. [12]

      Mingyuan Pang , Yiping Su , Haohao Zhang , Laixin Hong , Yue Wang , Yujie Ma , Min Yang , Mengge Guo , Zimai Wang , Zhen Kong , Jiajia Ye , Juan An , Guanglei Wu . Co-construction of sulfur and tin vacancies in Bi2S3@Sn0.904O2 as a durable anode for lithium-ion batteries. Acta Physico-Chimica Sinica, 2026, 42(11): 100368-0. doi: 10.1016/j.actphy.2026.100368

    13. [13]

      Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129

    14. [14]

      Qianli Ma , Tianbing Song , Tianle He , Xirong Zhang , Huanming Xiong . Sulfur-doped carbon dots: a novel bifunctional electrolyte additive for high-performance aqueous zinc-ion batteries. Acta Physico-Chimica Sinica, 2025, 41(9): 100106-0. doi: 10.1016/j.actphy.2025.100106

    15. [15]

      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

    16. [16]

      Yang Li ,  Yuxuan Zhang ,  Yuhai Tang ,  Lijuan Wang . Iodide anion-catalyzed green synthesis of m-cresol. University Chemistry, 2026, 41(7): 326-333. doi: 10.12461/PKU.DXHX202506054

    17. [17]

      Ruiqi Zhi ,  Xizhe Yang ,  Xinquan Zheng ,  Jian Jin . 弹不弹,硫“说了算”. University Chemistry, 2026, 41(10): 197-202. doi: 10.12461/PKU.DXHX202510015

    18. [18]

      Fengcheng Jia ,  Zixia Zheng ,  Fei Li ,  Huiqin Duan ,  Gang Wang . 串联SNAr/Aldol缩合构建季碳稠合吲哚啉. University Chemistry, 2026, 41(5): 190-197. doi: 10.12461/PKU.DXHX202511104

    19. [19]

      Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . Surface Sulfur Species Influence Hydrogenation Performance of Palladium-Sulfur Nanosheets. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-0. doi: 10.3866/PKU.WHXB202309043

    20. [20]

      Haozhe Hu ,  Haoyu Zhang ,  Changsheng Lu . Study on the Precipitation Process of Elemental Sulfur from the Decomposition Products of Thiosulfuric Acid: Is It an Unexpected Failed Experiment?. University Chemistry, 2025, 40(11): 409-415. doi: 10.12461/PKU.DXHX202412034

Metrics
  • PDF Downloads(9)
  • Abstract views(2862)
  • HTML views(488)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return