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

Cen Jinghe ^a,, ,
Yang Kai ^b,, ,
Li Jianxiao ^a,, ,
Li Can ^a ,
Yang Shaorong ^a,,

a.
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640
b.
School of Pharmaceutical Sciences, Gannan Medical University, Ganzhou 341000

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.
- ionic liquids,
- indoles,
- thiols,
- 3-arylsulfenylation reaction
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
1. [1]
  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
2. [2]
  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
3. [3]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
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]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . 表面硫物种对钯-硫纳米片加氢性能的影响. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-. doi: 10.3866/PKU.WHXB202309043
6. [6]
  Yiming Liang , Ziyan Pan , Kin Shing Chan . One Drink, Two Tears in the Central Nervous System: The Perils of Disulfiram-Like Reactions. University Chemistry, 2025, 40(4): 322-325. doi: 10.12461/PKU.DXHX202406016
7. [7]
  Hongyao Li , Youyan Liu , Luwei Dai , Min Yang , Qihui Wang . The Blessing of Indium Sulfide：Confronting the Narrow Path with Uric Acid. University Chemistry, 2024, 39(5): 325-335. doi: 10.3866/PKU.DXHX202311104
8. [8]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
9. [9]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
10. [10]
  Ruiqing LIU , Wenxiu LIU , Kun XIE , Yiran LIU , Hui CHENG , Xiaoyu WANG , Chenxu TIAN , Xiujing LIN , Xiaomiao FENG . Three-dimensional porous titanium nitride as a highly efficient sulfur host. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 867-876. doi: 10.11862/CJIC.20230441
11. [11]
  Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . 三聚氰胺泡沫支撑的S型硫铟锌镉/硫掺杂氮化碳异质结的绿色H₂O₂合成：协同界面电荷转移调控与局域光热效应. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-. doi: 10.1016/j.actphy.2025.100093
12. [12]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
13. [13]
  Yingtong Shi , Guotong Xu , Guizeng Liang , Di Lan , Siyuan Zhang , Yanru Wang , Daohao Li , Guanglei Wu . PEG-VN改性PP隔膜用于高稳定性高效率锂硫电池. Acta Physico-Chimica Sinica, 2025, 41(7): 100082-. doi: 10.1016/j.actphy.2025.100082
14. [14]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
15. [15]
  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
16. [16]
  Yangrui Xu , Yewei Ren , Xinlin Liu , Hongping Li , Ziyang Lu . 具有高传质和亲和表面的NH₂-UIO-66基疏水多孔液体用于增强CO₂光还原. Acta Physico-Chimica Sinica, 2024, 40(11): 2403032-. doi: 10.3866/PKU.WHXB202403032
17. [17]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
18. [18]
  Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382
19. [19]
  Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
20. [20]
  Pingping LU , Shuguang ZHANG , Peipei ZHANG , Aiyun NI . Preparation of zinc sulfate open frameworks based probe materials and detection of Pb²⁺ and Fe³⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 959-968. doi: 10.11862/CJIC.20240411

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1714)
HTML views(210)

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