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

doi:10.6023/cjoc201707005

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (12): 3213-3219.DOI: 10.6023/cjoc201707005 Previous Articles Next Articles

Articles

碱性离子液体中吲哚与芳基硫酚的3-芳烃硫基化反应

岑竞鹤^a, 杨凯^b, 李建晓^a, 李灿^a, 杨少容^a

a 华南理工大学化学与化工学院广州 510640;
b 赣南医学院药学院赣州 341000

收稿日期:2017-07-05 修回日期:2017-08-16 发布日期:2017-08-18
通讯作者: 李建晓, 杨少容 E-mail:cejxli@scut.edu.cn;lisryang@scut.edu.cn
基金资助:
国家自然科学基金（Nos.21502055，21642005）、中央高校基本科研业务费（No.2015ZM150）和中国博士后科学基金（No.2016T90779）资助项目.

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

Received:2017-07-05 Revised:2017-08-16 Published:2017-08-18
Contact: 10.6023/cjoc201707005 E-mail:cejxli@scut.edu.cn;lisryang@scut.edu.cn
Supported by:
Project 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).

1. Direct 3-Arylsulfenylation of Indoles with Thiols in Basic Ionic Liquid.PDF(788KB)

Abstract

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.

Key words: ionic liquids, indoles, thiols, 3-arylsulfenylation reaction

Cite this article

Cen Jinghe, Yang Kai, Li Jianxiao, Li Can, Yang Shaorong. Direct 3-Arylsulfenylation of Indoles with Thiols in Basic Ionic Liquid[J]. Chin. J. Org. Chem., 2017, 37(12): 3213-3219.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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] (a) Metzner, P.; Thuillier, A.; Katritzky, A. R.; Rees, C. W. Sulfur Reagents in Organic Synthesis, Academic Press, London, 1994.
(b) Wirth, T. Organoselenium Chemistry:Modern Developments in Organic Synthesis, Springer Verlag, Berlin, NY, 2000.
(c) Zhang, B.; Kang, Y.; Shi, R. Chin. J. Org. Chem. 2016, 36, 1814(in Chinese). (张变香, 亢永强, 史瑞雪, 有机化学, 2016, 36, 1814.)
[3] Bierbeek, A. V.; Gingras, M. Tetrahedron Lett. 1998, 39, 6283.
[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] (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] (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] (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] (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] (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] Funk, C. D. Nat. Rev. Drug Discovery 2005, 4, 664.
[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] (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] (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] (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] (a) Li, J.; Yang, S.; Jiang, H.; Wu, W.; Zhao, J. J. Org. Chem. 2013, 78, 12477.
(b) Li, J.; Yang, S.; Huang, L.; Chen, H.; Jiang, H. RSC Adv. 2013, 3, 11529.
(c) Li, J.; Yang, S.; Wu, W.; Jiang, H. Chem. Commun. 2014, 50, 1381.
(d) Li, J.; Zhu, Z.; Yang, S.; Zhang, Z.; Wu, W.; Jiang, H. J. Org. Chem. 2015, 80, 3870.
(e) An, Y.; Li, J.; Zhang, Z.; Li, C.; Yang, S. Chin. J. Org. Chem. 2016, 36, 2136(in Chinese). (安艳妮, 李建晓, 张振明, 李春生, 杨少容, 有机化学, 2016, 36, 2136.)
(f) An, Y.; Li, J.; Li, M.; Li, C.; Yang, S. Chin. J. Org. Chem. 2017, 37, 720(in Chinese). (安艳妮, 李建晓, 李蒙, 李春生, 杨少容, 有机化学, 2017, 37, 720.)
(g) Li, J.; An, Y.; Li, J.; Yang, S.; Wu, W.; Jiang, H. Org. Chem. Front. 2017, 4, 1590.
[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] Dou, H.; Gao, S.; Fu, Z.; Liu, S. Chin. J. Org. Chem. 2011, 31, 1056(in Chinese). (窦辉, 高思旖, 付召龙, 刘士忠, 有机化学, 2011, 31, 1056.)
[18] Sang, P.; Chen, Z.; Zou, J.; Zhang, Y. Green Chem. 2013, 15, 2096.
[19] Huang, D.; Chen, J.; Dan, W.; Ding, J.; Liu, M.; Wu, H. Adv. Synth. Catal. 2012, 354, 2123.
[20] Tudge, M.; Tamiya, M.; Savarin, C.; Humphrey, G. R. Org. Lett. 2006, 8, 565.
[21] Guo, Y.-J.; Tang, R.-Y.; Li, J.-H.; Zhong, P.; Zhang, X.-G. Adv. Synth. Catal. 2009, 351, 2615.

碱性离子液体中吲哚与芳基硫酚的3-芳烃硫基化反应

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

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yi Wang, Jian Zhang, Yangzi Liu, Xiaoyan Luo, Weiping Deng. Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2864-2877.
[2]	Yijun Shi, Xinyue Sun, Han Cao, Fusheng Bie, Jie Ma, Zhe Liu, Xingshun Cong. Thioesterification of Esters with Primary Aliphatic Thiols at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2499-2505.
[3]	Mingyang Pang, Honghong Chang, Zhang Feng, Juan Zhang. Recent Advances in Transition-Metal-Catalyzed Tandem Dearomatization of Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1271-1291.
[4]	Changyuan Du, Yucai Tang, Jinglin Duan, Biyu Yang, Yupeng He, Qian Zhou, Xuewen Liu. Organic-Dye-Catalyzed Visible-Light-Mediated Alkoxycarbon-ylation of 2-Aryl-N-acryloyl Indoles with Carbazates [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4268-4276.
[5]	Xuechun Zhao, Hui Fan, Yao Xu, Xiaoming Liao, Xiaoxiang Zhang. PPh₃-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3997-4002.
[6]	Fangjie Li, Bin Lu, Yang Liu, Xiaoming Wang. Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3390-3397.
[7]	Qisheng Gao, Qi Jing, Yang Chen, Jing Sun, Mingdong Zhou. Decarboxylative Amidation of Acrylamides with Oxamic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 257-265.
[8]	Hejiang Luo, Tongxiang Cao, Shifa Zhu. Divergent Synthesis of Ketone-Fused Indoles/Pyrroles via Metal-Guided Friedel-Crafts Cyclization [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3521-3531.
[9]	Sai Shu, Zhibin Huang, Yujie Chen, Shan Yang, Yaqiqi Jiang, jingyu Zhang, Yingsheng Zhao. Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3171-3179.
[10]	Yu Liu, Zan Chen, Pu Chen, Biquan Xiong, Jun Xie, An Liu, Yun Liang, Kewen Tang. Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2290-2301.
[11]	Rong Wang, Lichen Xu, Yi Lu, Bo Jiang, Wenjuan Hao. Sc(OTf)₃-Catalyzed Dearomatization of Indoles for the Synthesis of 3,3'-Bisindoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1582-1590.
[12]	Tao Wang, Xiaosha Wang, Yawen Song, Jingjing Huo, Jingshuan Zhou, Qingwei Kang, Lantao Liu. Cu(OAc)₂-Mediated C—H Bond Dithiolation of Amide-Oxazolines with Aryl Thiols [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1098-1107.
[13]	Yuying Du, Yeyuan Xiao, Fuli Tian, Limin Han, Yanlong Gu, Ning Zhu. Progress in Annulative Transformations from Indoles to Carbazoles: State of the Art [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 521-528.
[14]	Hehua Xu, Xiangtai Meng, Yu Zheng, Jinyue Luo, Shenlin Huang. Electrochemical Annulations of o-Alkynylanilines for Synthesis of 3-Iodoindoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4696-4703.
[15]	Zihui Ning, Xinhua Peng, Rui Bai, Shanshan Liu, Zhuo Li, Linyu Jiao. Iridium Catalyzed C—H Amidation of Benzamides with Phosphoryl Azides in Ionic Liquids [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4484-4492.