ARTICLES

β-H Regioselective Trifluoromethyl Sulfonylation of Aryl Ethylene

  • Linlin Xu ,
  • Meijun Lan ,
  • Muyu Zhang ,
  • Yongqi Zhang ,
  • Yuhao Feng ,
  • Liangce Rong ,
  • Jinpeng Zhang
Expand
  • aSchool of Public Health, Key Laboratory of Human Genetics and Environmental Medicine, Xuzhou Medical University, Xuzhou 221004
    bSchool of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116

Received date: 2022-02-11

  Revised date: 2022-04-06

  Online published: 2022-04-15

Supported by

Natural Science Foundation of the Jiangsu Higher Education Institutions of China(18KJA150004); Undergraduate Innovation and Entrepreneurship Training Program and the Brand Major of Universities in Jiangsu Province

Abstract

In the presence of cerium ammonium nitrate, the β-H radical sulfonation reaction of aryl ethylene with sodium trifluoromethanesulfinate was reported to give highly regioselective trans-alkene. The advantages of this method were cheap and easy to obtain reaction reagents, mild reaction conditions and simple operation. Moreover, the reaction had a high regioselective and configurational selectivity.

Cite this article

Linlin Xu , Meijun Lan , Muyu Zhang , Yongqi Zhang , Yuhao Feng , Liangce Rong , Jinpeng Zhang . β-H Regioselective Trifluoromethyl Sulfonylation of Aryl Ethylene[J]. Chinese Journal of Organic Chemistry, 2022 , 42(7) : 2134 -2139 . DOI: 10.6023/cjoc202202014

References

[1]
(a) He, S.; Yan, S.; Guo, W.; Zhai, G.; Zhang, W. Chin. J. Org. Chem. 2020, 40, 2094. (in Chinese)
[1]
何淑旺, 颜世强, 郭伟, 翟光喜, 张伟, 有机化学, 2020, 40, 2092).
[1]
(b) Wang, J.-Y.; Ma, L.; Li, Y.; Wang, X.-S. Chin. J. Org. Chem. 2019, 39, 232. (in Chinese)
[1]
( 王建勇, 马岚, 李彦, 王细胜, 有机化学, 2019, 39, 232)
[2]
(a) Prabhakar, P.; Parul, G..; Anand, S. Asian J. Org. Chem. 2018, 7, 111.
[2]
(b) Wolfgang, J. C.; Oliver;, K.; David, C. Chem.-Eur. J. 2018, 24, 17234.
[2]
(c) Shi, X.-K.; Ren, X.-Y.; Ren, Z.-Y.; Li, J.; Wang, Y.-L.; Yang, S.-Z.; Gu, J.-X.; Gao, Q.; Huang, G.-S. Eur. J. Org. Chem. 2014, 5083.
[2]
(d) Liu, K.; Li, D.-P.; Zhou, S.-F.; Pan, X.-Q.; Shoberu, A.; Zou, J.-P. Tetrahedron 2015, 71, 4031.
[2]
(e) Wang, H.-M.; Lu, Q.-Q.; Qian, C.-H.; Liu, C.; Liu, K.; Chen, K.; Lei, A. Angew. Chem., nt. Ed. 2016, 55, 1094.
[3]
(a) Hofman, K.; Liu, N.-W.; Manolikakes, G. Chem.-Eur. J. 2018, 24, 11852.
[3]
(b) Mampuys, P.; McElroy, C. R.; Clark, J. H.; Orru, R. V. A.; Maes, B. U. W. Adv. Synth. Catal. 2020, 362, 3.
[3]
(c) Xu, Z.; Zhai, R.; Liang, T.; Zhang, L. Chem.-Eur. J. 2017, 23, 14133.
[4]
(a) Devendar, P.; Yang, G. F. Sulfur Chemistry, Springer, Cham, 2019, pp. 35-78.
[4]
(b) Waldman, A. J.; Ng, T. L.; Wang, P.; Balskus, E. P. Chem. Rev. 2017, 117, 5784.
[4]
(c) Feng, M.; Tang, B.; H. Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.
[4]
(d) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.
[5]
(a) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.
[5]
(b) Kirsch, P.; Bremer, M. Angew. Chem., Int. Ed. 2000, 39, 4216.
[6]
(a) Hui, R.; Zhang, S.; Tan, Z.; Wu, X.; Feng, B. Chin. J. Org. Chem. 2017, 37, 3060. (in Chinese)
[6]
惠人杰, 张士伟, 谭政, 吴小培, 冯柏年, 有机化学, 2017, 37, 3060).
[7]
Li, M.; Kang, H.; Xue, X.-S.; Cheng, J.-P. Acta Chim. Sinica 2018, 76, 988. (in Chinese)
[7]
( 李曼, 康会英, 薛小松, 程津培, 化学学报, 2018, 76, 988.)
[8]
Hua, L. N.; Li, H.; Qing, F. L.; Huang, Y. G.; Xu, X. H. Org. Biomol. Chem. 2016, 14, 8443.
[9]
(a) Chen, W.; Guo, R.; Gong, J.; Yang, Z. Chin. J. Org. Chem. 2019, 39, 238. (in Chinese)
[9]
陈伟, 郭人予, 龚建贤, 杨震, 有机化学, 2019, 39, 238).
[9]
(b) Reddy, C. R.; Ajaykumar, U.; Kolgave, D. H. J. Org. Chem. 2020, 85, 15521.
Outlines

/