Synthesis of β-Sulfonyl Enamines via Iodine-Catalyzed Reaction between Vinyl Azides and Sodium Arylsulfinates

doi:10.6023/cjoc202106012

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 200-207.DOI: 10.6023/cjoc202106012 Previous Articles Next Articles

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碘催化乙烯基叠氮与芳基亚磺酸钠反应合成β-磺酰基烯胺

刘锐凯, 许峥, 宁志涛, 杜正银^*()

西北师范大学化学化工学院兰州 730070

收稿日期:2021-06-06 修回日期:2021-08-11 发布日期:2021-09-08
通讯作者: 杜正银
基金资助:
国家自然科学基金(21262028); 国家自然科学基金(21762039); 甘肃省自然科学基金(20JR5RA521)

Synthesis of β-Sulfonyl Enamines via Iodine-Catalyzed Reaction between Vinyl Azides and Sodium Arylsulfinates

Ruikai Liu, Zheng Xu, Zhitao Ning, Zhengyin Du()

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2021-06-06 Revised:2021-08-11 Published:2021-09-08
Contact: Zhengyin Du
Supported by:
National Natural Science Foundation of China(21262028); National Natural Science Foundation of China(21762039); Natural Science Foundation of Gansu Province(20JR5RA521)

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Abstract

The present protocol provides the facile and highly efficient synthesis of various Z-structure N-unprotected β-sulfonyl enamine compounds in a manner by using inexpensive molecular iodine as catalyst, vinyl azides as free radical acceptor, and sodium arylsulfinates as free radical sources. In this reaction, ethanol was used as solvent and bistrifluoromethanesulfonimide (Tf₂NH) was used as additive. The reaction was carried out at 40 ℃ for 4~6 h to obtain β-sulfonyl enamine compounds with good yields. The method does not need to use metal catalyst, and has the advantages of simple conditions, short reaction time and wide substrate application range.

Key words: iodine catalysis, vinyl azide, free radical addition, sulfonyl enamine

Cite this article

Ruikai Liu, Zheng Xu, Zhitao Ning, Zhengyin Du. Synthesis of β-Sulfonyl Enamines via Iodine-Catalyzed Reaction between Vinyl Azides and Sodium Arylsulfinates[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 200-207.

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References 38

[1]	Gu, P.; Su, Y.; Li, R. Org. Lett. 2012, 14, 2246. doi: 10.1021/ol3006437
[2]	Liu, Z.; Liao, P.; Bim, X. Org. Lett. 2014, 16, 3668. doi: 10.1021/ol501661k
[3]	Li, X.; Liao, S.; Zhang, L. Org. Lett. 2017, 19, 3687. doi: 10.1021/acs.orglett.7b01359
[4]	(a) Forster, M.; Newman, S. J. Chem. Soc. 1910, 97, 2570. doi: 10.1039/CT9109702570
	(b) Forster, M.; Newman, S. J. Chem. Soc. 1911, 99, 1277. doi: 10.1039/CT9119901277
[5]	Naresh Kumar Reddy, N.; Nageswara Rao, S.; Ravi, C.; Adimurthy, S. ACS Omega 2017, 2, 5235. doi: 10.1021/acsomega.7b00969 pmid: 31457795
[6]	Zhu, Z.; Tang, X.; Jiang, H. Org. Lett. 2017, 19, 1370. doi: 10.1021/acs.orglett.7b00203
[7]	Lei, W.; Wang, T.; Feng, K.; Wu, L.; Liu, Q. ACS Catal. 2017, 7, 7941. doi: 10.1021/acscatal.7b02818
[8]	Liu, Z.; Zhang, Z.; Zhu, G.; Zhou, Y.; Yan, L.; Gao, W.; Tong, L.; Tang, B. Org. Lett. 2019, 21, 7324. doi: 10.1021/acs.orglett.9b02616
[9]	Dey, R.; Banerjee, P. Org. Lett. 2017, 19, 304. doi: 10.1021/acs.orglett.6b03276
[10]	Wang, Y.; Hu, M.; Hayashi, H.; Xing, B.; Chiba, S. Org. Lett. 2016, 18, 992. doi: 10.1021/acs.orglett.6b00116
[11]	Lopez, E.; Lopez, L. Angew. Chem., nt. Ed. 2017, 56, 5121.
[12]	Rasool, F.; Ahmed, A.; Hussain, N.; Yousuf, S.; Mukherjee, D. Org. Lett. 2018, 20, 4036. doi: 10.1021/acs.orglett.8b01602
[13]	Das, D.; Kannaujiya, V.; Sadhu, M.; Ray, S.; Singh, V. J. Org. Chem. 2019, 84, 15865. doi: 10.1021/acs.joc.9b02127
[14]	Studer, A.; Curran, D. Angew. Chem., nt. Ed. 2016, 55, 58.
[15]	Sun, X.; Yu, S. Chem. Commun. 2016, 52, 10898. doi: 10.1039/C6CC05756J
[16]	Lei, W.; Feng, K.; Wang, T.; Wu, L.; Liu, Q. Org. Lett. 2018, 20, 7220. doi: 10.1021/acs.orglett.8b03147
[17]	Tang, P.; Zhang, C.; Chen, E.; Chen, B.; Chen, W.; Yu, Y. Tetrahedron Lett. 2017, 58, 2157. doi: 10.1016/j.tetlet.2017.04.069
[18]	Ning, Y.; Ji, Q.; Liao, P.; Anderson, E.; Bi, X. Angew. Chem., nt. Ed. 2017, 56, 13805.
[19]	Jung, H.; Kim, D. Synth. Commun. 2020, 50, 380. doi: 10.1080/00397911.2019.1696364
[20]	Banert, V. Angew. Chem., nt. Ed. 1985, 97, 231.
[21]	Wang, D.; Zhang, R.; Lin, S.; Deng, R.; Yan, Z. Chin. J. Org. Chem. 2016, 36, 2757. (in Chinese) doi: 10.6023/cjoc201604056
	(王丁意, 张荣兴, 林森, 邓瑞红, 严兆华, 有机化学, 2016, 36, 2757.) doi: 10.6023/cjoc201604056
[22]	(a) Mulina, O.; Ilovaisky, A.; Parshin, V.; Terent'ev, A. Adv. Synth. Catal. 2020, 362, 4579. doi: 10.1002/adsc.v362.21
	(b) Wei, W.; Liu, X.; Yang, D.; Dong, R.; Cui, Y.; Yuan, F.; Wang, H. Tetrahedron Lett. 2015, 56,1808. doi: 10.1016/j.tetlet.2015.02.043
	(c) Hu, F.; Gao, W.; Chang, H.; Li, X.; Wei, W. Chin. J. Org. Chem. 2015, 35, 1848. (in Chinese) doi: 10.6023/cjoc201504039
	(胡飞, 高文超, 常宏宏, 李兴, 魏文珑, 有机化学, 2015, 35, 1848.) doi: 10.6023/cjoc201504039
	(d) Chen, F.; Zhou, N.; Zhan, J.; Han, B.; Yu, W. Org. Chem. Front. 2017, 4, 135. doi: 10.1039/C6QO00535G
[23]	Terent'ev, A.; Mulina, O.; Pirgach, D.; Nikishin, G. Tetrahedron Lett. 2017, 73, 6871. doi: 10.1016/j.tet.2017.10.047
[24]	Yuan, Y.; Cao, Y.; Lin, Y.; Li, Y.; Huang, Z.; Lei, A. ACS Catal. 2018, 8, 10871. doi: 10.1021/acscatal.8b03302
[25]	Mulina, O.; Ilovaisky, A.; Opatz, T.; Terent’ev, A. Tetrahedron Lett. 2021, 64, 152737. doi: 10.1016/j.tetlet.2020.152737
[26]	(a) Tan, C.; Liu, Y.; Liu, H.; Xu, K.; Huang, S.; Wang, J.; Tan, J. Org. Chem. Front. 2020, 7, 780. doi: 10.1039/C9QO01489F
	(b) Yan, Y.; Xu, Y.; Niu, B.; Xie, H.; Liu, Y. J. Org. Chem. 2015, 80, 5581. doi: 10.1021/acs.joc.5b00474
	(c) Fan, W.; Yang, Z.; Jiang, B.; Li, G. Org. Chem. Front. 2017, 4, 1091. doi: 10.1039/C6QO00851H
[27]	Tang, X.; Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H. Angew. Chem. 2014, 126, 4289. doi: 10.1002/ange.201311217
[28]	Sun, X.; Lyu, Y.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Org. Lett. 2013, 15, 6222. doi: 10.1021/ol4030716
[29]	Gao, P.; Wang, J.; Bai, Z.; Shen, L.; Yan, Y.; Yang, D.; Fan, M.; Guan, Z. Org. Lett. 2016, 18, 6074. doi: 10.1021/acs.orglett.6b03060
[30]	Bohnen, C.; Bolm, C. Org. Lett. 2015, 17, 3011. doi: 10.1021/acs.orglett.5b01384
[31]	Tang, X.; Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H. Angew. Chem., nt. Ed. 2014, 53, 4205.
[32]	Ning, Y.; Zhao, X.; Wu, Y.; Bi, X. Org. Lett. 2017, 19, 6240. doi: 10.1021/acs.orglett.7b03204
[33]	(a) Gang, F.; Xu, G.; Dong, T.; Yang, L.; Du, Z. Chin. J. Org. Chem. 2015, 35, 1428. (in Chinese) doi: 10.6023/cjoc201502020
	(刚芳莉, 徐光利, 董涛生, 杨丽, 杜正银, 有机化学, 2015, 35, 1428.) doi: 10.6023/cjoc201502020
	(b) Xu, G.; Gang, F.; Dong, T.; Fu, Y.; Du, Z. Chin. J. Org. Chem. 2016, 36, 1513. (in Chinese) doi: 10.6023/cjoc201601028
	(徐光利, 刚芳莉, 董涛生, 傅颖, 杜正银, 有机化学, 2016, 36, 1513.) doi: 10.6023/cjoc201601028
	(c) Wu, H.; Wu, J.; Du, Z. Chin. J. Org. Chem. 2017, 37, 1127. (in Chinese) doi: 10.6023/cjoc201610034
	(吴慧, 武俊成, 杜正银, 有机化学, 2017, 37, 1127.) doi: 10.6023/cjoc201610034
	(d) Zhang, W.; Dong, T.; Wang, T.; Du, Z. J. Liaocheng Univ. (Nat. Sci.) 2019, 32, 35. (in Chinese)
	(张文莹, 董涛生, 王天昀, 杜正银, 聊城大学学报(自然科学版), 2019, 32, 35.)
	(e) Hu, B.; Zhang, Y.; Wang, T.; Du, Z. J. Liaocheng Univ. (Nat. Sci.) 2020, 33, 67. (in Chinese)
	(胡贝, 张源民, 王天昀, 杜正银, 聊城大学学报(自然科学版), 2020, 33, 67.)
	(f) Li, H.; Yang, P.; Xu, Z.; Du, Z.; Fu, Y. Chin. J. Org. Chem. 2020, 40, 2476. (in Chinese) doi: 10.6023/cjoc202002042
	(李怀贵, 杨澎, 许峥, 杜正银, 傅颖, 有机化学, 2020, 40, 2476.) doi: 10.6023/cjoc202002042
[34]	Pan, X.; Gao, J.; Liu, J.; Lai, J.; Jiang, H.; Yuan, G. Green Chem. 2015, 17, 1400. doi: 10.1039/C4GC02115K
[35]	Wang, Y.; HervLonca, G.; Chiba, S. Angew. Chem., Int. Ed. 2014, 53, 1067. doi: 10.1002/anie.201307846
[36]	Mulina, O.; Zhironkina, N.; Paveliev, S.; Demchuk, D.; Terent'ev, A. Org. Lett. 2020, 22, 1818. doi: 10.1021/acs.orglett.0c00139 pmid: 32077294
[37]	Liu, Q.; Zhang, J.; Zhao, G.; Lei, A. J. Am. Chem. Soc. 2013, 135, 11481. doi: 10.1021/ja4052685
[38]	Yi, D.; He, L.; Qi, Z.; Zhang, Z.; Li, M.; Fu, Q.; Wei, S. Chin. J. Chem. 2021, 39, 859. doi: 10.1002/cjoc.v39.4

Entry	Catalyst	Additive	Solvent	Yield^b/%
1	I₂	—	EtOH	53
2	—	—	EtOH	N.R.
3	I₂	—	H₂O	31
4	I₂	—	DCM	16
5	I₂	—	MeCN	17
6	I₂	—	MeOH	40
7	I₂	TsOH	EtOH	69
8	I₂	TfOH	EtOH	66
9	I₂	BF₃•Et₂O	EtOH	43
10	I₂	Tf₂NH	EtOH	81
11	I₂	Cu(OTf)₂	EtOH	77
12^c	I₂	Tf₂NH	EtOH	38
13^d	I₂	Tf₂NH	EtOH	Trace
14^e	I₂	Tf₂NH	EtOH	73
15^f	I₂	Tf₂NH	EtOH	79

Entry	Catalyst	Additive	Solvent	Yield^b/%
1	I₂	—	EtOH	53
2	—	—	EtOH	N.R.
3	I₂	—	H₂O	31
4	I₂	—	DCM	16
5	I₂	—	MeCN	17
6	I₂	—	MeOH	40
7	I₂	TsOH	EtOH	69
8	I₂	TfOH	EtOH	66
9	I₂	BF₃•Et₂O	EtOH	43
10	I₂	Tf₂NH	EtOH	81
11	I₂	Cu(OTf)₂	EtOH	77
12^c	I₂	Tf₂NH	EtOH	38
13^d	I₂	Tf₂NH	EtOH	Trace
14^e	I₂	Tf₂NH	EtOH	73
15^f	I₂	Tf₂NH	EtOH	79

Reaction conditions	Yield/% of 3aa
Standard condition	81
No I₂	0
NIS (3 equiv.) instead of I₂	73
NIS (4 equiv.) instead of I₂	68
Under N₂atmosphere	76
Add TEMPO (3 equiv.)	Trace

Reaction conditions	Yield/% of 3aa
Standard condition	81
No I₂	0
NIS (3 equiv.) instead of I₂	73
NIS (4 equiv.) instead of I₂	68
Under N₂atmosphere	76
Add TEMPO (3 equiv.)	Trace

碘催化乙烯基叠氮与芳基亚磺酸钠反应合成β-磺酰基烯胺

Synthesis of β-Sulfonyl Enamines via Iodine-Catalyzed Reaction between Vinyl Azides and Sodium Arylsulfinates

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[3]	Xu Zheng, Zhou Bingwei, Jin Hongwei, Liu Yunkui. K₂S₂O₈/H₂O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides [J]. Chin. J. Org. Chem., 2018, 38(7): 1823-1828.
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