Electrochemically Mediated S—N Bond Formation: Synthesis of Sulfenamides

doi:10.6023/cjoc202101017

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2354-2360.DOI: 10.6023/cjoc202101017 Previous Articles Next Articles

Special Issue: 有机电合成虚拟专辑；热点论文虚拟合集

ARTICLES

电化学介导的S—N键形成: 次磺酰胺化合物的简洁合成

何慕雪, 程诗砚, 潘永周, 唐海涛^*(), 潘英明^*()

广西师范大学化学与药学学院药物资源化学与分子工程国家重点实验室广西桂林 541004

收稿日期:2021-01-11 修回日期:2021-03-04 发布日期:2021-03-22
通讯作者: 唐海涛, 潘英明
基金资助:
国家自然科学基金(22061003)

Electrochemically Mediated S—N Bond Formation: Synthesis of Sulfenamides

Muxue He, Shiyan Cheng, Yongzhou Pan, Haitao Tang(), Yingming Pan()

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004

Received:2021-01-11 Revised:2021-03-04 Published:2021-03-22
Contact: Haitao Tang, Yingming Pan
Supported by:
National Natural Science Foundation of China(22061003)

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Abstract

A series of sulfenamide compounds are synthesized by electrooxidation of thiophenols and amines. The electrosynthesis reaction does not require metal catalysts and oxidizing reagents, and uses simple devices such as single- chamber electrolyzers and constant current electrolysis. This method featured broad substrate scope, ready availability of starting materials, operational simplicity and environmental friendly, which provides a new strategy for the simple and convenient synthesis of various sulfenamide derivatives.

Key words: sulfenamides, organic electrosynthesis, S—N bond formation, dehydrogenative coupling

Cite this article

Muxue He, Shiyan Cheng, Yongzhou Pan, Haitao Tang, Yingming Pan. Electrochemically Mediated S—N Bond Formation: Synthesis of Sulfenamides[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2354-2360.

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Fig. & Tab. 6

References 7

	(a) O'Driscoll, M.; Greenhalgh, K.; Young, A.; Turos, E.; Dickey, S.; Lim, D. V. Bioorg. Med. Chem. 2008, 16,7832.
	(b) Guarino, V. R.; Karunaratne, V.; Stella, V. J. Bioorg. Med. Chem. Lett. 2007, 17,4910.
	(c) Craine, L.; Raban, M. Chem. Rev. 1989, 89,689.
[1]	Klioze, S. S.; Allen, R. C.; Wilker, J. C.; Woodward, D. L. J. Med. Chem. 1980, 23,677.
	(a) Davis, F. A.; Friedman, A. J.; Kluger, E. W.; Skibo, E. B.; Fretz, E. R.; Milicia, A. P.; LeMasters, W. C.; Bentley, M. D.; Lacadie, J. A.; Douglass, I. B.. J. Org. Chem. 1977, 42,967.
	(b) Heimer, N. E.; Field, L. J. Org. Chem. 1970, 35,3012.
	(a) Laudadio, G.; Barmpoutsis, E.; Schotten, C.; Struik, L.; Govaerts, S.; Browne, D. L.; Noël, T.. J. Am. Chem. Soc. 2019, 141,5664.
	(b) Youseflouei, N.; Alizadeh, S.; Masoudi-Khoram, M.; Nematollahi, D.; Alizadeh, H. Electrochim. Acta 2020, 353,136451.
	(c) Ryu, S. H.; Ra, J.; Ko, H. M. Asian J. Org. Chem. 2020, 9,933.
[2]	Lee, C.; Wang, X.; Jang, H. Y. Org. Lett. 2015, 17,1130.
[3]	Liu, S.; Qi, Z.; Zhang, Z.; Qian, B. Org. Lett. 2019, 21,7722.
[4]	Dou, Y.; Huang, X.; Wang, H.; Yang, L.; Li, H.; Yuan, B.; Yang, G. Green Chem. 2017, 19,2491.
	(a) Wiebe, A.; Gieshoff, T.; Möhle, S.; Rodrigo, E.; Zirbes, M.; Waldvogel, S. R. Angew. Chem.,Int. Ed. 2018, 57,5594.
	(b) Wang, M.-R.; Wu, Y.-Z.; Yao, J.; Deng, L.; Pan, Y.-Y.; Huang, K.-B.; Tang, H.-T. Chin. J. Org. Chem. 2019, 39,3223(in Chinese).
	(王毛锐, 吴雨峥, 姚健, 邓黎, 潘英明, 黄克斌, 唐海涛, 有机化学, 2019, 39,3223.)
[5]	(a) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52,3339.
	(b) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117,13230.
	(c) Wang, X.-Y.; Zhong, Y.-F.; Mo, Z.-Y.; Wu, S.-H.; Xu, Y.-L.; Tang, H.-T.; Pan, Y.-M. Adv. Synth. Catal. 2021, 363,208.
	(d) Meng, X.-J.; Zhong, P.-F.; Wang, Y.-M.; Wang, H.-S.; Tang, H.-T.; Pan, Y.-M. Adv. Synth. Catal. 2020, 362,506.
	(e) Feng, E.-Q.; Hou, Z.-W.; Xu, H.-C. Chin. J. Org. Chem. 2019, 39,1424(in Chinese).
	(冯恩祺, 侯中伟, 徐海超, 有机化学, 2019, 39,1424.)
	(f) Yu, M.-M.; Shi, W.-Y.; Lei, A.-W. Sci. Sin. Chim. 2021, 51,188(in Chinese).
	(余明明, 史文研, 雷爱文, 中国科学: 化学, 2021, 51,188.)
	(g) Zhong, P.-F.; Lin, H,-M.; Wang, L.-W.; Mo, Z.-Y.; Meng, X.-J.; Tang, H.-T.; Pan, Y.-M. Green Chem. 2020, 22,6334.
[6]	(a) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52,3309.
	(b) Jiang, Y.; Xu, K.; Zeng, C.-C. Chem. Rev. 2017, 118,4485.
	(c) Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43,2492.
	(d) Liu, K.; Tang, S.; Wu, T.; Wang, S.; Zou, M.; Cong, H.; Lei, A. Nat. Commun. 2019, 10,639.
	(e) He, M.-X.; Mo, Z.-Y.; Wang, Z.-Q.; Cheng, S.-Y.; Xie, R.-R.; Tang, H.-T.; Pan, Y.-M.. Org. Lett. 2020, 22,724.
	(f) Yang, Q.-L.; Wang, X.-Y.; Weng, X.-J.; Yang, X.; Xu, X.-T.; Tong, X.-F.; Fang, P.; Wu, X.-Y.; Mei, T.-S. Acta Chim. Sinica 2019, 77,866(in Chinese).
	(杨启亮, 王向阳, 翁信军, 杨祥, 徐学涛, 童晓峰, 方萍, 伍新燕, 梅天胜, 化学学报, 2019, 77,866.)
	(g) Li, M.-F.; Wang, R.; He, W.-J.; Jiang, B. Chin. J. Org. Chem. 2020, 40,1540(in Chinese).
	(李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2020, 40,1540.)
	(h) Pan, C.; Liu, P.; Wu, A.-G.; Li, M.; Wen, L.-R.; Guo, W.-S.. Chin. J. Org. Chem. 2020, 40,2855(in Chinese).
	(潘超, 刘鹏, 武安国, 李明, 文丽荣, 郭维斯, 有机化学, 2020, 40,2855.)
[7]	Tang, S.; Liu, Y.; Li, L.; Ren, X.; Li, J.; Yang, G.; Li, H.; Yuan, B. Org. Biomol. Chem. 2019, 17,1370.
	Zhong, P.-F.; Lin, H.-M.; Wang, L.-W.; Mo, Z.-Y.; Meng, X.-J.; Tang, H.-T.; Pan. Y.-M. Green Chem. 2020, 22,6334.
	(a) Wang, P.; Tang, S.; Huang, P.; Lei, A. Angew. Chem., Int. Ed. 2017, 56,3009.
	(b) Wu, J.; Zhou, Y.; Zhou, Y.; Chiang, C. W.; Lei, A. ACS Catal. 2017, 7,8320.
	(c) Yang, Y. Z.; Song, R. J.; Li, J. H. Org. Lett. 2019, 21,3228.

Entry	Electrolyte	Solvent	Electrode	Temp./℃	Yield^b/%
1	TBAI	DMF	Pt(–) \| C(+)	80	78
2	NH₄I	DMF	Pt(–) \| C(+)	80	62
3	KI	DMF	Pt(–) \| C(+)	80	47
4	n-Bu₄NCl	DMF	Pt(–) \| C(+)	80	35
5	n-Bu₄NBF₄	DMF	Pt(–) \| C(+)	80	Trace
6	n-Bu₄NPF₆	DMF	Pt(–) \| C(+)	80	Trace
7	TBAI	CH₃CN	Pt(–) \| C(+)	80	54
8	TBAI	1,4-Dioxane	Pt(–) \| C(+)	80	NR
9	TBAI	DCE	Pt(–) \| C(+)	80	NR
10	TBAI	THF	Pt(–) \| C(+)	80	NR
11	TBAI	DMSO	Pt(–) \| C(+)	80	NR
12	TBAI	CH₃OH	Pt(–) \| C(+)	80	NR
13^c	TBAI	DMF	Pt(–) \| C(+)	80	NR
14	TBAI	DMF	Pt(–) \| RVC(+)	80	77
15	TBAI	DMF	Pt(–) \| C(+)	60	64
16	TBAI	DMF	Pt(–) \| C(+)	100	72

Entry	Electrolyte	Solvent	Electrode	Temp./℃	Yield^b/%
1	TBAI	DMF	Pt(–) \| C(+)	80	78
2	NH₄I	DMF	Pt(–) \| C(+)	80	62
3	KI	DMF	Pt(–) \| C(+)	80	47
4	n-Bu₄NCl	DMF	Pt(–) \| C(+)	80	35
5	n-Bu₄NBF₄	DMF	Pt(–) \| C(+)	80	Trace
6	n-Bu₄NPF₆	DMF	Pt(–) \| C(+)	80	Trace
7	TBAI	CH₃CN	Pt(–) \| C(+)	80	54
8	TBAI	1,4-Dioxane	Pt(–) \| C(+)	80	NR
9	TBAI	DCE	Pt(–) \| C(+)	80	NR
10	TBAI	THF	Pt(–) \| C(+)	80	NR
11	TBAI	DMSO	Pt(–) \| C(+)	80	NR
12	TBAI	CH₃OH	Pt(–) \| C(+)	80	NR
13^c	TBAI	DMF	Pt(–) \| C(+)	80	NR
14	TBAI	DMF	Pt(–) \| RVC(+)	80	77
15	TBAI	DMF	Pt(–) \| C(+)	60	64
16	TBAI	DMF	Pt(–) \| C(+)	100	72

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[12]	Feng Enqi, Hou Zhongwei, Xu Haichao. Electrochemical Synthesis of Tetrasubstituted Hydrazines by Dehydrogenative N-N Bond Formation [J]. Chin. J. Org. Chem., 2019, 39(5): 1424-1428.
[13]	Tang Hao, Luo Junfei, Xie Pan. Advances on the Synthesis of Aryl Ethers via Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2735-2743.
[14]	Yuan Sitian, Wang Yanhua, Qiu Guanyinsheng, Liu Jinbiao. Recent Advances in Radical Initiated C-N Bond Formation under Transition Metal-Free Conditions [J]. Chin. J. Org. Chem., 2017, 37(3): 566-576.
[15]	Yang Lifeng, Hui Renjie, Shan Hengyue, Gong Kai. Iodine-Catalyzed Functionalization of N-H Bond of Imidazoles [J]. Chin. J. Org. Chem., 2017, 37(12): 3242-3247.

电化学介导的S—N键形成: 次磺酰胺化合物的简洁合成

Electrochemically Mediated S—N Bond Formation: Synthesis of Sulfenamides

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