Recent Advances in Synthesis of 3-Sulfenylated Indoles

doi:10.6023/cjoc202211012

Abstract

3‑Sulfenylated indoles have been widely used in pharmaceutical and agrochemical industry due to their inherent potential biological activity. How to synthesize bioactive molecules containing such structural units via simple and efficient method, especially to achieve the selective construction of C—S bond on indole C-3 atom, has become an important means for the design and development of highly bioactive molecules in recent years. The recent development in the regioselective synthesis of 3-sulfenylated indoles via the direct sulfenylation of indoles at the C-3 position on the basis of different types of sulfenylating reagents is summarized.

Key words: sulfenylation, C—S bond, cross-coupling

Cite this article

Yuxing Tong, Ziwei Wang, Ben Liu, Yaowei Xu, Song Gao, Xiangbing Tang, Xinghua Zhang. Recent Advances in Synthesis of 3-Sulfenylated Indoles[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1310-1324.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 13

Scheme 1. Some biologically active 3-sulfanylindoles

Scheme 2. Transition metal-catalyzed the synthesis of 3?sul- fenylated indoles

Scheme 3. Preparation of 3?sulfenylated indoles promoted by I2/Oxidant

Scheme 4. Electrocatalytic synthesis of 3-sulfanylindoles

Scheme 5. Synthesis of 3?sulfenylated indoles induced by visible-light

Scheme 6. Cross-coupling of sodium sulfinates with indoles catalyzed by iodine

Scheme 7. Cross-coupling of indoles with sulfinic acids catalyzed by TsOH/n-Bu4NI

Scheme 8. Cross-coupling of indoles with aryl/alkyl sulfonyl chlorides catalyzed by iodine

Scheme 9. Iodine-catalyzed regioselective sulfenylation of indoles with sulfonyl hydrazides

Scheme 10. MgBr2-catalyzed sulfenylation of indoles with N- thioalkyl- and N-thioarylphthalimides

Scheme 11. CeCl3-catalyzed the synthesis of 3?sulfenylated indoles

Scheme 12. Cross-coupling of indoles with bunte salts catalyzed by iodine

Scheme 13. Synthesis of 3?sulfenylated indoles mediated by a hypervalent iodine(III) reagent

References 64

[1]	(a) Williams, T. M.; Ciccarone, T. M.; MacTough, S. C.; Rooney, C. S.; Balani, S. K.; Condra, J. H.; Emin, E. A.; Goldman, M. E.; Greenlee, W. J.; Kauffman, L. R.; O'Brien, J. A.; Sardana, V. V.; Schleif, W. A.; Theoharides, A. D.; Anderson, P. S. J. Med. Chem. 1993, 36, 1291. pmid: 2470904
	(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. doi: 10.1021/jm049360d pmid: 2470904
	(c) Funk, C. D. Nat. Rev. Drug Discovery 2005, 4, 664. doi: 10.1038/nrd1796 pmid: 2470904
	(d) Unangst, P. C.; Connor, D. T.; Stabler, S. R.; Weikert, R. J.; Carethers, M. E.; Kennedy J. A. Thueson, D. O.; Chestnut, J. C.; Adolphson, R. L.; Conroy, M. C. J. Med. Chem. 1989, 32, 1360. pmid: 2470904
	(d) Regina, G. L.; Bai, R.; Rensen, W. M.; Coluccia, A.; Piscitelli, F.; Gatti, V.; Bolognesi, A.; Lavecchia, A.; Granata, I.; Porta, A.; Maresca, B.; Soriani, A.; Iannitto, M. L.; Mariani, M.; Santoni, A.; Brancale, A.; Ferlini, C.; Dondio, G.; Varasi, M.; Mercurio, C.; Hamel, E.; Lavia, P.; Novellino, E.; Silvestri, R. J. Med. Chem. 2011, 54, 8394. doi: 10.1021/jm2012886 pmid: 2470904
[2]	Khandekar, S. S.; Gentry, D. R.; Aller, G, V.; Warren, P.; Xiang, H.; Silverman, C.; Doyle, M. L.; Chambers, P. A.; Konstantinidis, A. K.; Brandt, M.; Daines, R. A.; Lonsdale, J. T. J. Biol. Chem. 2001, 276, 30024. doi: 10.1074/jbc.M101769200 pmid: 11375394
[3]	Maeda, Y.; Koyabu, M.; Nishimura, T.; Uemura, S. J. Org. Chem. 2004, 69, 7688. doi: 10.1021/jo048758e
[4]	Yadav, J. S.; Reddy, B. V. S.; Reddy, Y. J.; Praneeth, K. Synthesis 2009, 1520.
[5]	Schlosser K. M. Krasutsky, A. P.; Hamilton, H. W.; Reed, J. E.; Sexton, K. Org. Lett. 2004, 6, 819. pmid: 14986983
[6]	Yadav, J. S.; Reddy, B. V. S.; Reddy, Y. J. Tetrahedron Lett. 2007, 48, 7034. doi: 10.1016/j.tetlet.2007.07.130
[7]	Zhang, H.; Bao, X.; Song, Y.; Qu, J.; Wang, B. Tetrahedron 2015, 71, 8885. doi: 10.1016/j.tet.2015.09.070
[8]	Yi, S.; Li, M.; Mo, W.; Hu, X.; Hu, B.; Sun, N.; Jin, L.; Shen, Z. Tetrahedron Lett. 2016, 57, 1912. doi: 10.1016/j.tetlet.2016.03.073
[9]	Liu, X.; Cui, H.; Yang, D.; Dai, S.; Zhang, G.; Wei, W.; Wang, H. Catal. Lett. 2016, 146, 1743. doi: 10.1007/s10562-016-1798-2
[10]	Ohkado, R.; Ishikawa, T.; Iida, H. Green Chem. 2018, 20, 984. doi: 10.1039/C8GC00117K
[11]	Choudhury, P.; Roy, B.; Basu, B. Asian J. Org. Chem. 2017, 6, 1569. doi: 10.1002/ajoc.v6.11
[12]	Chen, M.; Luo, Y.; Zhang, C.; Guo, L.; Wang, Q.; Wu, Y. Org. Chem. Front. 2019, 6, 116. doi: 10.1039/c8qo00726h
[13]	Benchawan, T.; Saeeng, R. Eur. J. Org. Chem. 2022, e202200752
[14]	Liu, Y.; Zhang, Y.; Hu, C.; Wan, J.-P.; Wen, C. RSC Adv. 2014, 4, 35528. doi: 10.1039/C4RA05206D
[15]	Truong, T. S.; Retailleau, P.; Nguyen, T. B. Asian J. Org. Chem. 2022, 11, e202100751.
[16]	Wang, P.; Tang, S.; Huang, P.; Lei, A. Angew. Chem., Int. Ed. 2017, 56, 1.
[17]	Guo, W.; Tan, W.; Zhao, M.; Tao, K.; Zheng, L.-Y.; Wu, Y.; Chen D.; Fan,, X.-L. RSC Adv. 2017, 7, 37739. doi: 10.1039/C7RA08086G
[18]	Hazarika, S.; Barman, P. ChemistrySelect 2020, 5, 11583. doi: 10.1002/slct.v5.37
[19]	Yuan, W.; Huang, J.; Xu, X.; Wang, L.; Tang, X.-Y. Org. Lett. 2021, 23, 7139. doi: 10.1021/acs.orglett.1c02553
[20]	Huang, Q.; Peng, X.; Li, H.; He, H.; Liu, L. Molecules 2022, 27, 772. doi: 10.3390/molecules27030772
[21]	Saima; Equbal, D.; Lavekara, A. G.; Sinha, A. K. Org. Biomol. Chem. 2016, 14, 6111. doi: 10.1039/c6ob00930a pmid: 27251465
[22]	Atkinson, J. G.; Hamel, P.; Girard, Y. Synthesis 1988, 480.
[23]	Regina, G. L.; Gatti, V.; Famiglini, V.; Piscitelli, F.; Silvestri, R. ACS Comb. Sci. 2012, 14, 258. doi: 10.1021/co200165j
[24]	Sang, P.; Chen, Z.; Zou, J.; Zhang, Y. Green Chem. 2013, 15, 2096. doi: 10.1039/c3gc40724a
[25]	Zhou, X.; Li, X. RSC Adv. 2014, 4, 1241. doi: 10.1039/C3RA46361C
[26]	Yu, Y.; Zhou, Y.; Song, Z.; Liang, G. Org. Biomol. Chem. 2018, 16, 4958. doi: 10.1039/C8OB00948A
[27]	Fang, X.-L.; Tang, R.-Y.; Zhong, P.; Li, J.-H. Synthesis 2009, 24, 4183.
[28]	Azeredo, J. B.; Godoi, M.; Martins, G. M.; Silveira, C. C.; Braga, A. L. J. Org. Chem. 2014, 79, 4125. doi: 10.1021/jo5000779
[29]	Huang, D.; Chen, J.; Dan, W.; Ding, J.; Liu, M.; Wu, H. Adv. Synth. Catal. 2012, 13, 2123.
[30]	Prasad, C. D.; Kumar, S.; Sattar, M.; Adhikary, A.; Kumar, S. Org. Biomol. Chem. 2013, 11, 8036. doi: 10.1039/c3ob41601a pmid: 24166084
[31]	Ye, L.-M.; Chen, J.; Mao, P.; Zhang, X.-J.; Yan, M. Tetrahedron Lett. 2017, 58, 2743.
[32]	Chen, C.; Niu, P.; Shen, Z.; Li, M. J. Electrochem. Soc. 2018, 165, G67.
[33]	Qin, J.; Zuo, H.; Ni, Y.; Yu, Q.; Zhong, F. ACS Sustainable Chem. Eng. 2020, 8, 12342. doi: 10.1021/acssuschemeng.0c03942
[34]	Xiao, F.; Xie, H.; Liu, S.; Deng, G.-J. Adv. Synth. Catal. 2014, 356, 364. doi: 10.1002/adsc.201300773
[35]	Rahaman, R.; Barman, P. Eur. J. Org. Chem. 2017, 6327.
[36]	Katrun, P.; Hongthong, S.; Hlekhlai, S.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Jaipetchb, T.; Kuhakarn, C. RSC Adv. 2014, 4, 18933. doi: 10.1039/c4ra02607a
[37]	Rao, H.; Wang, P.; Wang, J.; Li, Z.; Sun, X.; Cao, S. RSC Adv. 2014, 4, 49165. doi: 10.1039/C4RA08669D
[38]	Ge, X.; Sun, F.; Liu, X.; Chen, X.; Qian, C.; Zhou, S. New J. Chem. 2017, 41, 13175. doi: 10.1039/C7NJ02784B
[39]	Wang, F.; Lu, G.-P.; Lin, Y. Tetrahedron Lett. 2021, 70, 153015. doi: 10.1016/j.tetlet.2021.153015
[40]	Liang, J.; Wang, G.; Dong, L.; Pang, X.; Qin, J.; Xu, X.; Shao, X.; Li, Z. Org. Lett. 2021, 23, 5545. doi: 10.1021/acs.orglett.1c01882
[41]	Liu, C.-R.; Ding, L.-H. Org. Biomol. Chem. 2015, 13, 2251. doi: 10.1039/C4OB02575J
[42]	Rahaman, R.; Devi, N.; Bhagawati, J. R.; Barman, P. RSC Adv. 2016, 6, 18929. doi: 10.1039/C5RA26425A
[43]	Yang, X.; Bao, Y.; Dai, Z.; Zhou, Q.; Yang, F. Green Chem. 2018, 20, 3727. doi: 10.1039/C8GC01764F
[44]	Chen, L.; Zhang, J.; Wei, Y.; Yang, Z.; Liu, P.; Zhang, J.; Dai, B. Tetrahedron 2019, 75, 130664. doi: 10.1016/j.tet.2019.130664
[45]	Chen, M.; Huang, Z.-T.; Zheng, Q.-Y. Chem. Commun. 2012, 48, 11686. doi: 10.1039/c2cc36866h
[46]	Kumaraswamy, G.; Rajua, R.; Narayanarao, V. RSC Adv. 2015, 5, 22718. doi: 10.1039/C5RA00646E
[47]	Wang, D.; Guo, S.; Zhang, R.; Lin, S.; Yan, Z. RSC Adv. 2016, 6, 54377. doi: 10.1039/C6RA02302A
[48]	Wu, Z.; Li, Y.-C.; Ding, W.-Z.; Zhu, T.; Liu, S.-Z.; Ren, X.; Zou, L.-H. Asian J. Org. Chem. 2016, 5, 625. doi: 10.1002/ajoc.201600096
[49]	Ghosh, A.; Lecomte, M.; Kim-Lee, S.-H.; Radosevich, A. T. Angew. Chem., Int. Ed. 2019, 58, 2864. doi: 10.1002/anie.v58.9
[50]	Yang, F.-L.; Tian, S.-K. Angew. Chem. 2013, 125, 5029. doi: 10.1002/ange.v125.18
[51]	Yang, Y.; Zhang, S.; Tang, L.; Hu, Y.; Zha, Z.; Wang, Z. Green Chem. 2016, 18, 2609. doi: 10.1039/C6GC00313C
[52]	Mumtaz, Y.; Liu, J. Asian J. Org. Chem. 2022, 11, e202200104.
[53]	Tudge, M.; Tamiya, M.; Savarin, C.; Humphrey, G. R. Org. Lett. 2006, 8, 565. doi: 10.1021/ol052615c
[54]	Silveira, C. C.; Mendes, S. R.; Wolf, L.; Martins, G. M. Tetrahedron Lett. 2010, 51, 2014. doi: 10.1016/j.tetlet.2010.02.038
[55]	Marcantoni, E.; Cipolletti, R.; Marsili, L.; Menichetti, S.; Properzi, R.; Viglianisi, C. Eur. J. Org. Chem. 2013, 132.
[56]	Qi, H.; Zhang, T.; Wan, K.; Luo, M. J. Org. Chem. 2016, 81, 4262. doi: 10.1021/acs.joc.6b00636
[57]	Gupta, P. K.; Yadav, A. K.; Sharma, A. K.; Singh, K. N. Org. Biomol. Chem. 2021, 19, 3484. doi: 10.1039/D1OB00377A
[58]	Li, J.; Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Org. Biomol. Chem. 2016, 14, 9384. doi: 10.1039/C6OB01528J
[59]	Li, J.; Li, C.; Yang, S.; An, Y.; Wu, W.; Jiang, H. J. Org. Chem. 2016, 81, 7771. doi: 10.1021/acs.joc.6b01428
[60]	Pandey, A. K.; Chand, S.; Singh, R.; Kumar, S.; Singh, K. N. ACS Omega 2020, 5, 7627. doi: 10.1021/acsomega.0c00472 pmid: 32280906
[61]	Leng, F.; Huang, J.; Yu, N.; Wang, G. Tetrahedron Lett. 2021, 85, 153488. doi: 10.1016/j.tetlet.2021.153488
[62]	Zhang, L.-Y.; Wu, Y.-H.; Wang, N.-X.; Gao, X.-W.; Yan, Z.; Xu, B.-C.; Liu, N.; Wang, B.-Z.; Xing, Y. Eur. J. Org. Chem. 2021, 1446.
[63]	Cironis, N.; Yuan, K.; Thomas, S. P.; Ingleson, M. J. Eur. J. Org. Chem. 2022, e202101394.
[64]	Zhang, B.; Li, X.; Li, X.; Yu, Z.; Zhao, B.; Wang, X.; Du, Y.; Zhao, K. J. Org. Chem. 2021, 86, 17274. doi: 10.1021/acs.joc.1c02404

吲哚-3-硫醚类化合物的合成研究进展