SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 2: 584 - 592

DOI: https://doi.org/10.6023/cjoc202306023

ARTICLES

Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst

  • Wenwen Chen ,
  • Qin Zhang ,
  • Songyue Zhang ,
  • Fangfang Huang ,
  • Xinyin Zhang ,
  • Jianfeng Jia
Expand
  • Key Laboratory of Magnetic Molecules & Magnetic Information Materials Ministry of Education, School of Chemical and Material Science, Shanxi Normal University, Taiyuan 030031
† The authors contributed equally to this work.
* Corresponding authors. E-mail: ;

Received date: 2023-06-26

  Revised date: 2023-09-20

  Online published: 2023-10-26

Supported by

Natural Science Foundation of Shanxi Province(202203021221134); Postgraduate Education Teaching Reform Topic of Shanxi Province(2022YJJG136)

Fold

Abstract

The cross-coupling reaction between alkynyl iodide and sodium sulphinate catalyzed by visible light, leading to the construction of acetylene sulfone, is reported. The synthesis method is simple and green, and does not require any photo- catalyst and additive. The reaction has high efficiency and good functional group compatibility. In addition, the scale-up experiment can also obtain good yield, which further proves the practical application value of the reaction.

Key words： alkyne sulfone; visible light; alkynyl iodine; sodium sulphinate; coupling reaction

Cite this article

Wenwen Chen , Qin Zhang , Songyue Zhang , Fangfang Huang , Xinyin Zhang , Jianfeng Jia . Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst[J]. Chinese Journal of Organic Chemistry, 2024 , 44(2) : 584 -592 . DOI: 10.6023/cjoc202306023

References

[1]
Feng, M. H.; Tang, B. Q.; Liang, S. H.; Jiang, X. F. Curr. Top. Med. Chem. 2016, 16, 1200.
[2]
Balaburski, G. M.; Leu, J. I.-J.; Beeharry, N.; Hayik, S.; Andrake, M. D.; Zhang, G.; Herlyn, M.; Villanueva, J.; Dunbrack Jr, R. L.; Yen, T.; George, D. L.; Murphy, M. E. Mol. Cancer Res. 2013, 11, 219.
[3]
Selling, H. A.; Tempe, A. Pestic. Sci. 1976, 7, 19.
[4]
(a) Huang, X.; Duan, D.; Zheng, W. ChemInfor. 2003, 34, 1958.
[4]
(b) Xie, M.; Wang, J.; Gu, X.; Sun, Y.; Wang, S. Org. Lett. 2006, 8, 431.
[5]
(a) Xiao, Q.; Lu, M.; Deng, Y.; Jian, J.-X.; Tong, Q.-X.; Zhong, J.-J. Org. Lett. 2021, 23, 9303.
[5]
(b) Jia, J.; Ho, Y. A.; Bulow, R. F. Chemistr. 2018, 24, 14054.
[5]
(c) Song, W.; Zheng, N.; Li, M.; Dong, K.; Li, J.; Ullah, K.; Zheng, Y. Org. Lett. 2018, 20, 6705.
[5]
(d) Wang, S.; Liu, C.; Jia, J.; Zha, C.; Xie, M.; Zhang, N. Tetrahedro. 2016, 72, 6684.
[5]
(e) Zhou, X.; Yu, S.; Qi, Z.; Li, X. Sci. China Chem. 2015, 58, 1297.
[6]
(a) Fang, K.; Xie, M.; Zhang, Z.; Ning, P.; Shu, G. Tetrahedron Lett. 2013, 54, 3819.
[6]
(b) Guo, A.; Han, J. B.; Zhu, L.; Wei, Y. ; Org. Lett. 2019, 21, 2927.
[6]
(c) Jin, W.; Wu, M.; Xiong, Z.; Zhu, G. Chem. Commun. 2018, 54, 7924.
[7]
(a) Truce, W. E.; Hill, H. E.; Boudakia, M. M. J. Am. Chem. Soc. 1956, 78, 2760.
[7]
(b) Laba, V. I.; Polievktov, M. K.; Prilezhaeva, E. N.; Mairanovskii, S. G. Bull. Acad. Sci. USSR. Div. Chem. Sci. 1969, 18, 2004.
[7]
(c) Corlay, H.; Lewis, R. T.; Motherwell, W. B.; Shipman, M. Tetrahedro. 1995, 51, 3303.
[7]
(d) Zaburdaeva, E. A.; Dodonov, V. A. Russ. Chem. Bull. 2011, 185.
[8]
(a) Truce, W. E.; Wolf, G. C. J. Org. Chem. 1971, 36, 1727.
[8]
(b) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633.
[8]
(c) Nair, V.; Augustine, A.; Suja, T. D. Synthesi. 2002, 2259.
[8]
(d) Qi, D.; Dong, W.; Peng, Z.; Zhang, Y.; An, D. Tetrahedro. 2019, 75, 130427.
[9]
(a) Miura, T.; Kobayashi, M. J. Chem. Soc.. Chem. Commun. 1982, 438.
[9]
(b) Bhaskar, R. D.; Chandrasekhar, B. N.; Padmavathi, V.; Padmaja, A. Tetrahedro. 1997, 53, 17351.
[9]
(c) Qian, H.; Huang, X. Tetrahedron Lett. 2002, 43, 1059.
[10]
Suzuki, H.; Abe, H. Tetrahedron Lett. 1996, 37, 3717.
[11]
(a) Liu, Z. D.; Chen, Z. C. Synth. Commun. 1992, 22, 1997.
[11]
(b) Huang, X.; Zhu, Q. Tetrahedron Lett. 2001, 42, 6373.
[11]
(c) Wei, W.; Wen, J.; Yang, D.; Jing, H.; You, J.; Wang, H. RSC Adv. 2015, 5, 4416.
[11]
(d) Raghuvanshi, D. S.; Verma, N. Org. Biomol. Chem. 2021, 19, 4760.
[11]
(e) Meesin, J.; Katrun, P.; Pareseecharoen, C.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Kuhakarn, C. J. Org. Chem. 2016, 81, 2744.
[11]
(f) Dai, C.; Wang, J.; Deng, S.; Zhou, C.; Zhang, W.; Zhu, Q.; Tang, X. RSC Adv. 2017, 7, 36112.
[11]
(g) Wang, L.; Wei, W.; Yang, D.; Cui, H.; Yue, H.; Wang, H. Tetrahedron Lett. 2017, 58, 4799.
[11]
(h) Mo, Z. Y.; Zhang, Y. Z.; Huang, G. B.; Wang, X. Y.; Pan, Y. M.; Tang, H. T. Adv. Synth. Catal. 2020, 362, 2160.
[11]
(i) Meng, X.; Xu, H.; Cao, X.; Cai, X. M.; Luo, J.; Wang, F.; Huang, S. Org. Lett. 2020, 22, 6827.
[11]
(j) Gong, X.; Yang, M.; Liu, J. B.; He, F. S.; Wu, J. Org. Chem. Fron. 2020, 7, 938.
[12]
(a) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Acc. Chem. Res. 2016, 49, 1911.
[12]
(b) Zhou, Q. Q.; Zou, Y. Q.; Lu, L. Q.; Xiao, W. J. Angew. Chem.. Int. Ed. 2019, 58, 1586.
[13]
Wang, X.; Li, X.; Tian, B.; Xiao, H.; Chen, W.; Wu, H.; Jia, J. Arabian J. Chem. 2022, 15, 103708.
[14]
(a) Zhang, L.; Wei, C.; Wu, J.; Liu, D.; Yao, Y.; Chen Z.; Liu, J, ; Yao, C.-J.; Li, D.; Yang, R.; Xia, Z. Chem. Sci. 2022, 13, 7475.
[14]
(b) Amos, S. G. E.; Cavalli, D.; Vaillant, F. L.; Waser, J. Angew. Chem.. Int. Ed. 2021, 60, 23827.
[15]
(a) Fang, Z; Zhang, Y.; Zhang, Z.; Song, Q.; Wu, Y.; Liu, Z.; Ning, Y. Org. Lett. 2022, 6374.
[15]
(b) Aleti, R. R.; Festa, A. A.; Storozhenko, O. A.; Bondarev, V. L.; Segida, O. O.; Paveliev, S. A.; Rybakov, V. B.; Varlamov, A. V.; Voskressensky, L. G. Org. Lett. 2022, 24, 9337.
[15]
(c) Wang, Y.; Tang, K.; Liu, Z.; Ning, Y. Chem. Commun. 2020, 56, 13141.
[16]
Chen, P.; Zhu, C.; Zhu, R.; Wu, W.; Jiang, H. Chem. Asian J. 2017, 12, 1875.
Options
Outlines

/

〈 〉