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
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
(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.
Bierbeek, A. V.; Gingras, M. Tetrahedron Lett. 1998, 39, 6283.
doi: 10.1016/S0040-4039(98)01327-6
(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.
(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.
(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.
(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.
(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.
(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.
Funk, C. D. Nat. Rev. Drug Discovery 2005, 4, 664.
doi: 10.1038/nrd1796
(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.
(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.
(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.
(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.
(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.
Dou, H.; Gao, S.; Fu, Z.; Liu, S. Chin. J. Org. Chem. 2011, 31, 1056(in Chinese).
Sang, P.; Chen, Z.; Zou, J.; Zhang, Y. Green Chem. 2013, 15, 2096.
doi: 10.1039/c3gc40724a
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
Tudge, M.; Tamiya, M.; Savarin, C.; Humphrey, G. R. Org. Lett. 2006, 8, 565.
doi: 10.1021/ol052615c
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
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
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
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
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
Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
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
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
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
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
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
Haitao Wang , Lianglang Yu , Jizhou Jiang , Arramel , Jing Zou . S-Doping of the N-Sites of g-C3N4 to Enhance Photocatalytic H2 Evolution Activity. Acta Physico-Chimica Sinica, 2024, 40(5): 2305047-0. doi: 10.3866/PKU.WHXB202305047
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
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
Yan'e LIU , Shengli JIA , Yifan JIANG , Qinghua ZHAO , Yi LI , Xinshu CHANG . MoO3/cellulose derived carbon aerogel: Fabrication and performance as cathode for lithium-sulfur battery. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1565-1573. doi: 10.11862/CJIC.20250054
Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
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
Chuan′an DING , Weibo YAN , Shaoying WANG , Hao XIN . Preparation of wide-band gap copper indium gallium sulfide solar cells by solution method. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1755-1764. doi: 10.11862/CJIC.20250198
Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO2 Methanation of Derived Ni-Al2O3 Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002
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
Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . Green H2O2 synthesis via melamine-foam supported S-scheme Cd0.5Zn0.5In2S4/S-doped carbon nitride heterojunction: synergistic interfacial charge transfer and local photothermal effect. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-0. doi: 10.1016/j.actphy.2025.100093