SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 1: 200 - 207

DOI: https://doi.org/10.6023/cjoc202106012

ARTICLES

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

  • Ruikai Liu ,
  • Zheng Xu ,
  • Zhitao Ning ,
  • Zhengyin Du
Expand
  • College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
* Corresponding author. E-mail:

Received date: 2021-06-06

  Revised date: 2021-08-11

  Online published: 2021-09-08

Supported by

National Natural Science Foundation of China(21262028); National Natural Science Foundation of China(21762039); Natural Science Foundation of Gansu Province(20JR5RA521)

Fold

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 . DOI: 10.6023/cjoc202106012

References

[1]
Gu, P.; Su, Y.; Li, R. Org. Lett. 2012, 14, 2246.
[2]
Liu, Z.; Liao, P.; Bim, X. Org. Lett. 2014, 16, 3668.
[3]
Li, X.; Liao, S.; Zhang, L. Org. Lett. 2017, 19, 3687.
[4]
(a) Forster, M.; Newman, S. J. Chem. Soc. 1910, 97, 2570.
[4]
(b) Forster, M.; Newman, S. J. Chem. Soc. 1911, 99, 1277.
[5]
Naresh Kumar Reddy, N.; Nageswara Rao, S.; Ravi, C.; Adimurthy, S. ACS Omega 2017, 2, 5235.
[6]
Zhu, Z.; Tang, X.; Jiang, H. Org. Lett. 2017, 19, 1370.
[7]
Lei, W.; Wang, T.; Feng, K.; Wu, L.; Liu, Q. ACS Catal. 2017, 7, 7941.
[8]
Liu, Z.; Zhang, Z.; Zhu, G.; Zhou, Y.; Yan, L.; Gao, W.; Tong, L.; Tang, B. Org. Lett. 2019, 21, 7324.
[9]
Dey, R.; Banerjee, P. Org. Lett. 2017, 19, 304.
[10]
Wang, Y.; Hu, M.; Hayashi, H.; Xing, B.; Chiba, S. Org. Lett. 2016, 18, 992.
[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.
[13]
Das, D.; Kannaujiya, V.; Sadhu, M.; Ray, S.; Singh, V. J. Org. Chem. 2019, 84, 15865.
[14]
Studer, A.; Curran, D. Angew. Chem., nt. Ed. 2016, 55, 58.
[15]
Sun, X.; Yu, S. Chem. Commun. 2016, 52, 10898.
[16]
Lei, W.; Feng, K.; Wang, T.; Wu, L.; Liu, Q. Org. Lett. 2018, 20, 7220.
[17]
Tang, P.; Zhang, C.; Chen, E.; Chen, B.; Chen, W.; Yu, Y. Tetrahedron Lett. 2017, 58, 2157.
[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.
[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)
[21]
(王丁意, 张荣兴, 林森, 邓瑞红, 严兆华, 有机化学, 2016, 36, 2757.)
[22]
(a) Mulina, O.; Ilovaisky, A.; Parshin, V.; Terent'ev, A. Adv. Synth. Catal. 2020, 362, 4579.
[22]
(b) Wei, W.; Liu, X.; Yang, D.; Dong, R.; Cui, Y.; Yuan, F.; Wang, H. Tetrahedron Lett. 2015, 56,1808.
[22]
(c) Hu, F.; Gao, W.; Chang, H.; Li, X.; Wei, W. Chin. J. Org. Chem. 2015, 35, 1848. (in Chinese)
[22]
(胡飞, 高文超, 常宏宏, 李兴, 魏文珑, 有机化学, 2015, 35, 1848.)
[22]
(d) Chen, F.; Zhou, N.; Zhan, J.; Han, B.; Yu, W. Org. Chem. Front. 2017, 4, 135.
[23]
Terent'ev, A.; Mulina, O.; Pirgach, D.; Nikishin, G. Tetrahedron Lett. 2017, 73, 6871.
[24]
Yuan, Y.; Cao, Y.; Lin, Y.; Li, Y.; Huang, Z.; Lei, A. ACS Catal. 2018, 8, 10871.
[25]
Mulina, O.; Ilovaisky, A.; Opatz, T.; Terent’ev, A. Tetrahedron Lett. 2021, 64, 152737.
[26]
(a) Tan, C.; Liu, Y.; Liu, H.; Xu, K.; Huang, S.; Wang, J.; Tan, J. Org. Chem. Front. 2020, 7, 780.
[26]
(b) Yan, Y.; Xu, Y.; Niu, B.; Xie, H.; Liu, Y. J. Org. Chem. 2015, 80, 5581.
[26]
(c) Fan, W.; Yang, Z.; Jiang, B.; Li, G. Org. Chem. Front. 2017, 4, 1091.
[27]
Tang, X.; Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H. Angew. Chem. 2014, 126, 4289.
[28]
Sun, X.; Lyu, Y.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Org. Lett. 2013, 15, 6222.
[29]
Gao, P.; Wang, J.; Bai, Z.; Shen, L.; Yan, Y.; Yang, D.; Fan, M.; Guan, Z. Org. Lett. 2016, 18, 6074.
[30]
Bohnen, C.; Bolm, C. Org. Lett. 2015, 17, 3011.
[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.
[33]
(a) Gang, F.; Xu, G.; Dong, T.; Yang, L.; Du, Z. Chin. J. Org. Chem. 2015, 35, 1428. (in Chinese)
[33]
(刚芳莉, 徐光利, 董涛生, 杨丽, 杜正银, 有机化学, 2015, 35, 1428.)
[33]
(b) Xu, G.; Gang, F.; Dong, T.; Fu, Y.; Du, Z. Chin. J. Org. Chem. 2016, 36, 1513. (in Chinese)
[33]
(徐光利, 刚芳莉, 董涛生, 傅颖, 杜正银, 有机化学, 2016, 36, 1513.)
[33]
(c) Wu, H.; Wu, J.; Du, Z. Chin. J. Org. Chem. 2017, 37, 1127. (in Chinese)
[33]
(吴慧, 武俊成, 杜正银, 有机化学, 2017, 37, 1127.)
[33]
(d) Zhang, W.; Dong, T.; Wang, T.; Du, Z. J. Liaocheng Univ. (Nat. Sci.) 2019, 32, 35. (in Chinese)
[33]
(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.)
[33]
(e) Hu, B.; Zhang, Y.; Wang, T.; Du, Z. J. Liaocheng Univ. (Nat. Sci.) 2020, 33, 67. (in Chinese)
[33]
(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.)
[33]
(f) Li, H.; Yang, P.; Xu, Z.; Du, Z.; Fu, Y. Chin. J. Org. Chem. 2020, 40, 2476. (in Chinese)
[33]
(李怀贵, 杨澎, 许峥, 杜正银, 傅颖, 有机化学, 2020, 40, 2476.)
[34]
Pan, X.; Gao, J.; Liu, J.; Lai, J.; Jiang, H.; Yuan, G. Green Chem. 2015, 17, 1400.
[35]
Wang, Y.; HervLonca, G.; Chiba, S. Angew. Chem., Int. Ed. 2014, 53, 1067.
[36]
Mulina, O.; Zhironkina, N.; Paveliev, S.; Demchuk, D.; Terent'ev, A. Org. Lett. 2020, 22, 1818.
[37]
Liu, Q.; Zhang, J.; Zhao, G.; Lei, A. J. Am. Chem. Soc. 2013, 135, 11481.
[38]
Yi, D.; He, L.; Qi, Z.; Zhang, Z.; Li, M.; Fu, Q.; Wei, S. Chin. J. Chem. 2021, 39, 859.
Options
Outlines

/

〈 〉