SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 12: 4275 - 4281

DOI: https://doi.org/10.6023/cjoc202209041

ARTICLES

Electrochemical Oxidative Thiocyanosulfonylation of Aryl Acetylenes

  • Yu Zheng ,
  • Shencheng Qian ,
  • Pengcheng Xu ,
  • Binnan Zheng ,
  • Shenlin Huang
Expand
  • a Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037
    b International Innovation Center for Forest Chemicals and Materials, Nanjing 210037
    c Ningxia Best Pharmaceutical Chemical Co. Ltd., Yinchuan 750411
*E-mail:

Received date: 2022-09-30

  Revised date: 2022-11-24

  Online published: 2022-12-12

Supported by

National Natural Science Foundation of China(32171724); Natural Science Foundation of Jiangsu Province(BK20210607)

Fold

Abstract

Thiocyano and sulfonyl groups as important functional groups are widely existing in natural products, agrochemicals and medicines. They are also versatile synthetic intermediates that could be converted into various functionalities. There are limited reports on the synthesis of compounds that contain these two functional groups. A simple three-component thiocyanatosulfonylation of aryl acetylenes with sodium sulfinates and NH4SCN through electrochemical oxidation to construct thiocyanated vinylsulfones has been established. The reaction employs easily accessible starting materials and features the characterization of external oxidant-free, mild reaction conditions, and high stereoselectivity. Moreover, this method enables two C—S bonds to be simultaneously formed in a one-step reaction.

Key words： alkyne; difunctionalization; electrochemistry; radical; thiocyanation; sulfonylation; green chemistry

Cite this article

Yu Zheng , Shencheng Qian , Pengcheng Xu , Binnan Zheng , Shenlin Huang . Electrochemical Oxidative Thiocyanosulfonylation of Aryl Acetylenes[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4275 -4281 . DOI: 10.6023/cjoc202209041

References

[1]
(a) Chinchilla, R.; Nájera, C. Chem. Rev. 2014, 114, 1783.
[1]
(b) Trost, B. M.; Master, J. T. Chem. Soc. Rev. 2016, 45, 2212.
[1]
(c) Yang, X.-H.; Song, R.-J.; Xie, Y.-X.; Li, J.-H. ChemCatChem 2016, 8, 2429.
[1]
(d) Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7, 3100.
[1]
(e) Li, J.; He, D.; Lin, Z.; Wu, W.; Jiang, H. Org. Chem. Front. 2021, 8, 3502.
[1]
(f) Xie, Y.; Huang, L.; Qi, Y.; Hu, J.; Song, L.; Feng, H. Green Chem. 2022, 24, 1978.
[2]
For selected reviews, see: (a) Xu, L.; Wang, F.; Chen, F.; Zhu, S.; Chu, L. Chin. J. Org. Chem. 2022, 42, 1. (in Chinese)
[2]
( 徐磊, 王方, 陈凡, 朱圣卿, 储玲玲, 有机化学, 2022, 42, 1.)
[2]
(b) Zhang, Y.; Vessally, E. RSC Adv. 2021, 11, 33447.
[2]
(c) Whyte, A.; Torelli, A.; Mirabi, B.; Zhang, A.; Lautens, M. ACS Catal. 2020, 10, 11578.
[2]
(d) Mei, H.; Yin, Z.; Liu, J.; Sun, H.; Han, J. Chin. J. Chem. 2019, 37, 292.
[2]
(e) Ren, X.; Lu, Z. Chin. J. Catal. 2019, 40, 1003.
[3]
Selected examples of transition metal-catalyzed difunctionalization of alkynes, see: (a) Zhan, Y.-Z.; Meng, H.; Shu, W. Chem. Sci. 2022, 13, 4930.
[3]
(b) Yang, L.-F.; Wang, Q.-A.; Li, J.-H. Org. Lett. 2021, 23, 6553.
[3]
(c) Li, X.; He, S.; Song, Q. Org. Lett. 2021, 23, 2994.
[3]
(d) Sun, Q.; Li, L.; Liu, L.; Yang, Y.; Zhang, Z.; Wang, Z. Sci. China: Chem. 2019, 62, 904.
[3]
(e) Israr, M.; Xiong, H.; Li, Y.; Bao, H. Org. Lett. 2019, 21, 7078.
[3]
(f) Xiang, Y.; Kuang, Y.; Wu, J. Chem.-Eur. J. 2017, 23, 6996.
[3]
(g) Ning, Y.; Ji, Q.; Liao, P.; Anderson, E. A.; Bi, X. Angew. Chem., Int. Ed. 2017, 56, 13805.
[3]
(h) Jiang, G.; Zhu, C.; Li, J.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2017, 359, 1208.
[3]
(i) Li, Z.; García-Domínguez, A.; Nevado, C. J. Am. Chem. Soc. 2015, 137, 11610.
[4]
Selected examples of metal-free difunctionalization of alkynes, see: (a) Ma, C.; Xie, J.; Zeng, X.; Wei, Z.; Wei, Y. Org. Chem. Front. 2022, 9, 4441.
[4]
(b) Wu, H.; Shao, C.; Wu, D.; Jiang, L.; Yin, H.; Chen, F.-X. J. Org. Chem. 2021, 86, 5327.
[4]
(c) Ding, W.; Chai, J.; Wu, J.; Yoshikai, N. J. Am. Chem. Soc. 2020, 142, 8619.
[4]
(d) Ansari, M. Y.; Swarnkar, S.; Kumar, A. Chem. Commun. 2020, 56, 9561.
[4]
(e) Ansari, M. Y.; Kumar, N.; Kumar, A. Org. Lett. 2019, 21, 3931.
[4]
(f) Lu, L.-H.; Zhou, S.-J.; Sun, M.; Chen, J.-L.; Xia, W.; Yu, X.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 1574.
[4]
(g) Lu, Q.; Zhang, J.; Zhao, G.; Qi, Y.; Wang, H.; Lei, A. J. Am. Chem. Soc. 2013, 135, 11481.
[5]
Selected examples of visible light-induced difunctionalization of alkynes, see: (a) Xie, W.; Ma, P.; Zhang, Y.; Xi, L.; Qiu, S.; Huang, X.; Yang, B.; Gao, Y.; Zhang, J. Org. Lett. 2022, 24, 6099.
[5]
(b) Zhang, Q.; Li, X.; Zhang, W.; Wang, Y.; Pan, Y. Org. Lett. 2021, 23, 5410.
[5]
(c) Kumar, J.; Ahmad, A.; Rizvi, M. A.; Ganie, M. A.; Khajuria, C.; Shah, B. A. Org. Lett. 2020, 22, 5661.
[5]
(d) Peng, Z.; Yin, H.; Zhang, H.; Jia, T. Org. Lett. 2020, 22, 5885.
[5]
(e) Zhang, R.; Xu, P.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem. 2019, 84, 12324.
[5]
(f) Sahoo, A. K.; Dahiya, A.; Das, B.; Behera, A.; Patel, B. K. J. Org. Chem. 2019, 84, 12324.
[5]
(g) Guo, L.; Song, F.; Zhu, S.; Li, H.; Chu, L. Nat. Commun. 2018, 9, 4543.
[5]
(h) Liu, T.; Ding, Y.; Fan, X.; Wu, J. Org. Chem. Front. 2018, 5, 3153.
[6]
Selected examples of electrochemical induced difunctionalization of alkynes, see: (a) Hong, Z.-W.; Li, L.; Wang, L. Org. Chem. Front. 2022, 9, 2815.
[6]
(b) Sharma, D.; Hussain, Y.; Sharma, M.; Chauhan, P. Green, Chem. 2022, 24, 4783.
[6]
(c) Hu, J.; Zeng, L.; Hu, J.; Ma, R.; Liu, X.; Jiao, Y.; He, H.; Chen, S.; Xu, Z.; Wang, H.; Lei, A. Org. Lett. 2022, 24, 289.
[6]
(d) Yu, M.; Wang, H.; Gao, Y.; Bu, F.; Cong, H.; Lei, A. Cell Rep. Phy. Sci. 2021, 2, 100476.
[6]
(e) Du, W.-B.; Wang, N.-N.; Pan, C.; Ni, S.-F.; Wen, L.-R.; Li, M.; Zhang, L.-B. Green Chem. 2021, 23, 2420.
[6]
(f) Zhang, X.; Lu, D.; Wang, Z. Eur. J. Org.Chem. 2021, 2021, 4284.
[6]
(g) Kong, X.; Yu, K.; Chen, Q.; Xu, B. Asian J. Org. Chem. 2020, 9, 1760.
[6]
(h) Sattler, L. E.; Hilt, G. Chem.-Eur. J. 2021, 27, 605.
[7]
(a) Dean, L. J.; Prinsep, M. R. Nat. Prod. Rep. 2017, 34, 1359.
[7]
(b) Bayarmagnai, B.; Matheis, C.; Jouvin, K.; Goossen, L. J. Angew. Chem., Int. Ed. 2015, 54, 5753.
[7]
(c) Castanheiro, T.; Suffert, J.; Donnard, M.; Gulea, M. Chem. Soc. Rev. 2016, 45, 494.
[7]
(d) Zhang, L.; Niu, C.; Yang, X.; Qiu, H.; Yang, J.; Wen, J.; Wang, H. Chin. J. Org. Chem. 2020, 40, 1117. (in Chinese)
[7]
( 张龙菲, 牛聪, 杨晓婷, 秦宏云, 杨建静, 文江伟, 王桦, 有机化学, 2022, 40, 1117.)
[7]
(e) Xu, Q.; Zhang, L.; Feng, G.; Jin, C. Chin. J. Org. Chem. 2019, 39, 287. (in Chinese)
[7]
( 徐庆, 张连阳, 冯高峰, 金城安, 有机化学, 2019, 39, 287.)
[8]
(a) Chang, M.-Y.; Cheng, Y.-C. Org. Lett. 2016, 18, 1682.
[8]
(b) Sun, X. M.; Yu, F.; Ye, T. T.; Liang, X. M.; Ye, J. X. Chem.-Eur. J. 2011, 17, 430.
[8]
(c) Meadows, D. C.; Sanchez, T.; Neamati, N.; North, T. W.; Gervay-Hague, J. Bioorg. Med. Chem. 2007, 15, 1127.
[8]
(d) Frankel, B. A.; Bentley, M.; Kruger, R. G.; McCafferty, D. G. J. Am. Chem. Soc. 2004, 126, 3404.
[9]
Lu, L.-H.; Zhou, S.-J.; He, W.-B.; Xia, W.; Chen, P.; Yu, X.; Xu, X.; He, W.-M. Org. Biomol. Chem. 2018, 16, 9064.
[10]
Samanta, S.; Chatterjee, R.; Santra, S.; Hajra, A.; Khalymbadzha, I. A.; Zyryanov, G. V.; Majee, A. ACS Omega 2018, 3, 13081.
[11]
Liu, Z.; Yang, L.; Zhang, K.; Chen, W.; Yu, T.; Wang, L.; Gao, W.; Tang, B. Org. Lett. 2020, 22, 2081.
[12]
Wang, Y.; Tang, K.; Liu, Z.; Ning, Y. Chem. Commun. 2020, 56, 13141.
[13]
Zhang, M.; Zeng, X. Org. Lett. 2021, 23, 3326.
[14]
(a) Lu, L.; Shi, R.; Lei, A. Trends in Chem. 2022, 4, 179.
[14]
(b) Shi, S.-H.; Liang, Y.; Jiao, N. Chem. Rev. 2021, 121, 485.
[14]
(c) Novaes, L. F. T.; Liu, J.; Shen, Y.; Lu, L.; Meinhardt, J. M.; Lin, S. Chem. Soc. Rev. 2021, 50, 7941.
[14]
(d) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339.
[14]
(e) Wiebe, A.; Gieshoff, T.; M?hle, S.; Rodrigo, E.; Zirbes, M.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2018, 57, 5594.
[14]
(f) Yoshida, J.-I.; Shimizu, A.; Hayashi, R. Chem. Rev. 2018, 118, 4702.
[14]
(g) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
[15]
(a) Vicente, D. A.; Galdino, D.; Navarro, M.; Menezes, P. H. Green Chem. 2020, 22, 5262.
[15]
(b) Qian, P.; Bi, M.; Su, J.; Zha, Z.; Wang, Z. J. Org. Chem. 2016, 81, 4876.
[15]
(c) Lu, F.; Zhang, K.; Yao, Y.; Yin, Y.; Chen, J.; Zhang, X.; Wang, Y.; Lu, L.; Gao, Z.; Lei, A. Green Chem. 2021, 23, 763.
[16]
Zhang, X.; Lu, D.; Wang, Z. Eur. J. Org. Chem. 2021, 2021, 4284.
Options
Outlines

/

〈 〉