SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 1: 186 - 194

DOI: https://doi.org/10.6023/cjoc202207012

Electrochemical Oxidative C(sp3)—H Sulfonylation of Xanthenes with Sodium Sulfinates

  • Bin Wei ,
  • Zilong Zhou ,
  • Jinghao Qin ,
  • Zeyu Yan ,
  • Jiacheng Guo ,
  • Shu Lei ,
  • Yexiang Xie ,
  • Xuanhui Ouyang ,
  • Renjie Song
Expand
  • Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063
† These authors contributed equally to this work.
* Corresponding authors. E-mail: ;
;

Received date: 2022-07-05

  Revised date: 2022-07-29

  Online published: 2022-09-15

Supported by

National Natural Science Foundation of China(51878326); National Natural Science Foundation of China(21861027); National Natural Science Foundation of China(22161030); National Natural Science Foundation of China(21901100); Natural Science Foundation of Jiangxi Province(20212ACB203007); Natural Science Foundation of Jiangxi Province(20204BCJ23010); Natural Science Foundation of Jiangxi Province(20202ACBL216017); Natural Science Foundation of Jiangxi Province(20212AEI91002); Natural Science Foundation of Jiangxi Province(20202ACB203002); Natural Science Foundation of Jiangxi Provincial Education Department(GJJ210906); Natural Science Foundation of Jiangxi Provincial Education Department(GJJ210909)

Fold

Abstract

A direct electrochemical sulfonylation of C(sp3)—H bonds of xanthenes with sodium sulfinates was studied. A wide variety of 9-(arylsulfonyl)-9H-xanthenes and 9-(alkylsulfonyl)-9H-xanthenes were constructed in a single step at room temperature. This reaction proceeded through a radical pathway and a new C—S bond was formed under this electrochemical sulfonylation transformation. The significant advantages of this strategy include transition metal- and additional oxidant-free, mild reaction conditions, operational simplicity, broad substrate scope and excellent functional group tolerance.

Key words： electrooxidation; sulfonylation; xanthene; sodium sulfinate

Cite this article

Bin Wei , Zilong Zhou , Jinghao Qin , Zeyu Yan , Jiacheng Guo , Shu Lei , Yexiang Xie , Xuanhui Ouyang , Renjie Song . Electrochemical Oxidative C(sp3)—H Sulfonylation of Xanthenes with Sodium Sulfinates[J]. Chinese Journal of Organic Chemistry, 2023 , 43(1) : 186 -194 . DOI: 10.6023/cjoc202207012

References

[1]
(a) Lin, X.-Y.; Yang, Y.-Y.; Zhao, Y.-H.; Fu, Q.-L. Ecotoxicology 2012, 21, 1281.
[1]
(b) Foote, K. M.; Blades, K.; Cronin, A.; Fillery, S.; Guichard, S. S.; Hassall, L.; Hickson, I.; Jacq, X.; Jewsbury, P. J.; McGuire, T. M.; Nissink, J. W. M.; Odedra, R.; Page, K.; Perkins, P.; Suleman, A.; Tam, K.; Thommes, P.; Broadhurst, R.; Wood, C. J. Med. Chem. 2013, 56, 2125.
[1]
(c) Navada, S. C.; Silverman, L. R. Expert Rev. Anticancer Ther. 2016, 16, 805.
[1]
(d) Takeda, Y.; Kuroki, K.; Chinen, T.; Kitagawa, D. Cell Struct. Funct. 2020, 45, 57.
[2]
(a) Wang, M.; Zhao, J.-Y.; Jiang, X.-F. ChemSusChem 2019, 12, 3064.
[2]
(b) Ye, S.-Q.; Zheng, D.-Q.; Wu, J.; Qiu, G. Chem. Commun. 2019, 55, 2214.
[2]
(c) Zhang, J.; Xie, W.-L.; Ye, S.-Q.; Wu, J. Org. Chem. Front. 2019, 6, 2254.
[2]
(d) Chen, S.-H.; Li, Y.-P.; Wang, M.; Jiang, X.-F. Green Chem. 2020, 22, 322.
[2]
(e) Meng, Y.-Y.; Wang, M.; Jiang, X.-F. Angew. Chem., Int. Ed. 2020, 59, 1346.
[2]
(f) Ye, S.-Q.; Zhou, K.-D.; Rojsitthisak, P.; Wu, J. Org. Chem. Front. 2020, 7, 14.
[3]
(a) Wang, N.-Z.; Saidhareddy, P.; Jiang, X.-F. Nat. Prod. Rep. 2020, 37, 246.
[3]
(b) Wei, B.; Li, K.-W.; Wu, Y.-C.; Tong, S.-Q.; Song, R.-J. Synthesis 2020, 52, 3855.
[3]
(c) Ye, S.-Q.; Li, X.-F.; Xie, W.-L.; Wu, J. Eur. J. Org. Chem. 2020, 2020, 1274.
[3]
(d) Tong, S.-Q.; Li, K.-W.; Ouyang, X.-H.; Song, R.-J.; Li, J.-H. Green Synth. Catal. 2021, 2, 145.
[4]
(a) Yamamoto, H.; Nakata, K. Eur. J. Org. Chem. 2019, 2019, 4906.
[4]
(b) Kanyiva, K. S.; Uchida, K.; Shibata, T. Bull. Chem. Soc. Jpn. 2021, 94, 1377.
[4]
(c) Wang, X.-L.; Bai, X.; Wu, C.-F.; Dong, Y.-X.; Zhang, M.; Fan, L.-L.; Tang, L.; Yang, Y.-Y.; Zhang, J.-Q. Asian J. Org. Chem. 2021, 10, 386.
[5]
(a) Wei, W.-T.; Zhou, M.-B.; Fan, J.-H.; Liu, W.; Song, R.-J.; Liu, Y.; Hu, M.; Xie, P.; Li, J.-H. Angew. Chem., Int. Ed. 2013, 52, 3638.
[5]
(b) Zuo, Z.-W.; Ahneman, D. T.; Chu, L.-L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
[5]
(c) Tang, S.; Xu, Z.-H.; Liu, T.; Wang, S.-W.; Yu, J.; Liu, J.; Hong, Y.; Chen, S.-L.; He, J.; Li, J.-H. Angew. Chem., Int. Ed. 2021, 60, 21360.
[6]
(a) Lin, M.-Y.; Xu, K.; Jiang, Y.-Y.; Liu, Y.-G.; Sun, B.-G.; Zeng, C.-C. Adv. Synth. Catal. 2018, 360, 1665.
[6]
(b) Li, K.-J.; Jiang, Y.-Y.; Xu, K.; Zeng, C.-C.; Sun, B.-G. Green Chem. 2019, 21, 4412.
[6]
(c) Yang, Y.-Z.; Song, R.-J.; Li, J.-H. Org. Lett. 2019, 21, 3228.
[6]
(d) Yang, Y.-Z.; Wu, Y.-C.; Song, R.-J.; Li, J.-H. Chem. Commun. 2020, 56, 7585.
[6]
(e) Wei, B.; Qin, J.-H.; Yang, Y.-Z.; Xie, Y.-X.; Ouyang, X.-H.; Song, R.-J. Org. Chem. Front. 2022, 9, 816.
[7]
(a) Xie, Y.-Y.; Wang, Y.-C.; He, Y.; Hu, D.-C.; Wang, H.-S.; Pan, Y.-M. Green Chem. 2017, 19, 656.
[7]
(b) Wang, Y.-C.; Liu, L.-Q.; Wang, G.-M.; Ouyang, H.; Li, Y.-J. Green Chem. 2018, 20, 604.
[7]
(c) Wu, Y.-C.; Jiang, S.-S.; Song, R.-J.; Li, J.-H. Chem. Commun. 2019, 55, 4371.
[7]
(d) Qin, J.-H.; Luo, M.-J.; An, D.-L.; Li, J.-H. Angew. Chem., Int. Ed. 2020, 60, 1861.
[7]
(e) Li, J.; Zhang, S.; Xu, K. Chin. Chem. Lett. 2021, 32, 2729.
[8]
Wei, W.-J.; Zhong, Y.-J.; Feng, Y.-F.; Gao, L.; Tang, H.-T.; Pan, Y.-M.; Ma, X.-L.; Mo, Z.-Y. Adv. Synth. Catal. 2022, 364, 726.
[9]
CCDC 2131087 (3aa) contain the supplementary crystallo-graphic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
[10]
(a) Luo, M.-J.; Liu, B.; Li, Y.; Hu, M.; Li, J.-H. Adv. Synth. Catal. 2019, 361, 1538.
[10]
(b) Wu, Y.-C.; Jiang, S.-S.; Luo, S.-Z.; Song, R.-J.; Li, J.-H. Chem. Commun. 2019, 55, 8995.
Options
Outlines

/

〈 〉