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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 12: 4639 - 4650

DOI: https://doi.org/10.6023/cjoc202107022

REVIEWS

Recent Advances in Arylations and Sulfonylations of Arylazo Sulfones

  • Na Meng ,
  • Qishun Liu ,
  • Ruisheng Liu ,
  • Yufen Lü ,
  • Xiaohui Zhao ,
  • Wei Wei
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  • a School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
    b Key Laboratory of Tibetan Medicine Research, Chinese Academy of Sciences, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, Qinghai 810008
† These authors contributed equally to this work.
* Corresponding authors. E-mail: ;
;

Received date: 2021-07-07

  Revised date: 2021-07-29

  Online published: 2021-08-10

Supported by

Youth Innovation and Technology Project of Higher School in Shandong Province(2019KJC021); 2018 CAS "Light of West China" Program

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Abstract

Aromatic ring- and sulfone-containing compounds are widely used in the fields of synthetic chemistry, medicinal chemistry and material chemistry. Therefore, it is of great significance to develop a simple, green and efficient method to construct aryl and sulfonyl compounds. Arylazo sulfones can be used as arylation or sulfonylation reagents to access aryl and sulfonyl compounds via hemolytic cleavage of C—N and N—S bonds to generate aryl radical and sulfonyl radical. In this review, the recent research progress of arylations and sulfonylations using arylazo sulfones is summarized. The synthetic methods and the related reaction mechanisms are highlighted, and an outlook of this research field is also given.

Key words： arylazo sulfones; photocatalysis; electrocatalytic; arylations; sulfonylations

Cite this article

Na Meng , Qishun Liu , Ruisheng Liu , Yufen Lü , Xiaohui Zhao , Wei Wei . Recent Advances in Arylations and Sulfonylations of Arylazo Sulfones[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4639 -4650 . DOI: 10.6023/cjoc202107022

References

[1]
(a) Hanson, J. R. Nat. Prod. Rep. 1995, 12, 381.
[1]
(b) Tietze, L. F.; Raschke, T. Synlett 1995, 597.
[2]
(a) Shiotani, S.; Kometani, T.; Mitsuhashi, K.; Nozawa, T.; Kurobe, A.; Futsukaichi, O. J. Med. Chem. 1976, 19, 803.
[2]
(b) Smethurst, P. W. R.; Forrest, W. H.; Hayden, J. Br. J. Anaesth. 1971, 43, 1129.
[3]
(a) Roll, D. M.; Scheuer, P. J.; Matsumoto, G. K.; Clardy, J. J. Am. Chem. Soc. 1983, 105, 6177.
[3]
(b) Yano, H.; Nakanishi, S. J. Biol. Chem. 1993, 268, 25846.
[4]
Yuan, Z. Z.; Dai, Q.; Qiao, L.; Zhao, Y. Y.; Zhang, H. M.; Li, X. F. J. Membr. Sci. 2017, 541, 465.
[5]
(a) Mack, D. J.; Njardarson, J. T. Angew. Chem., Int. Ed. 2013, 52, 1543.
[5]
(b) Wang, N. Z.; Saidhareddy, P.; Jiang, X. F. Nat. Prod. Rep. 2020, 37, 246.
[6]
Yazdanyar, S.; Boer, J.; Ingvarsson, G.; Szepietowski, J. C.; Jemec, G. B. E. Dermatology 2011, 222, 342.
[7]
Li, P.; Hu, D. Y.; Xie, D. D.; Chen, J. X.; Jin, L. H.; Song, B. A. J. Agric. Food Chem. 2018, 66, 3093.
[8]
(a) Williams, T. M.; Ciccarone, T. M.; MacTough, S. C.; Rooney, C. S.; Balani, S. K.; Condra, J. H.; Emini, E. A.; Goldman, M. E.; Greenlee, W. J. J. Med. Chem. 1993, 36, 1291.
[8]
(b) Artico, M.; Silvestri, R.; Massa, S.; Loi, A. G.; Corrias, S.; Piras, G.; Colla, P. L. J. Med. Chem. 1996, 39, 522.
[9]
Kamigta, N.; Kobayashi, M. Sulfur Rep. 1982, 2, 87.
[10]
(a) Kice, J. L.; Gabrielsen, R. S. J. Org. Chem. 1970, 35, 1004.
[10]
(b) Kobayashi, M.; Gotoh, M.; Minato, H. J. Org. Chem. 1975, 40, 140.
[10]
(c) Evers, M. J.; Christiaens, L. E.; Guillaume, M. R.; Renson, M. J. J. Org. Chem. 1985, 50, 1779.
[10]
(d) Sapountzis, I.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 897.
[10]
(e) Qiu, D.; Lian, C.; Mao, J.; Fagnoni, M.; Protti, S. J. Org. Chem. 2020, 85, 12813.
[11]
(a) Gaikwad, D. S.; Pore, D. M. Synlett 2012, 23, 2631.
[11]
(b) Wang, L.; Bao, P.; Liu, W.; Liu, S.; Hu, C.; Yue, H.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189. (in Chinese)
[11]
( 王雷雷, 鲍鹏丽, 刘维伟, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.)
[12]
(a) Shen, Q. L.; Ogata, T.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 6586.
[12]
(b) Arockiam, P. B.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. Green Chem. 2013, 15, 67.
[12]
(c) Prades, A.; Poyatos, M.; Peris, E. Adv. Synth. Catal. 2010, 352, 1155.
[13]
(a) Rao Volla, C. M.; Vogel, P. Angew. Chem., Int. Ed. 2008, 47, 1305.
[13]
(b) Zeng, X. M.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 17638.
[14]
(a) Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 463.
[14]
(b) Vásquez-Céspedes, S.; Holtkamp, M.; Karst, U.; Glorius, F. Synlett 2017, 28, 2759.
[15]
(a) Kumar, M. R.; Park, K.; Lee, S. Adv. Synth. Catal. 2010, 352, 3255.
[15]
(b) Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2003, 5, 2911.
[16]
(a) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45, 2044.
[16]
(b) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506.
[16]
(c) He, W.-B.; Gao, L.-Q.; Chen, X.-J.; Wu, Z.-L.; Huang, Y.; Cao, Z.; Xu, X.-H.; He, W.-M. Chin. Chem. Lett. 2020, 31, 1895.
[16]
(d) Liu, Q.; Wang, L.; Yue, H.; Li, J.-S.; Luo, Z.; Wei, W. Green Chem. 2019, 21, 1609.
[16]
(e) Gan, Z.; Li, G.; Yang, X.; Yan, Q.; Xu, G.; Li, G.; Jiang, Y.-Y.; Yang, D. Sci. China: Chem. 2020, 63, 1652.
[16]
(f) Chen, J.-R.; Yan, D.-M.; Wei, Q.; Xiao, W.-J. ChemPhotoChem 2017, 1, 148.
[16]
(g) Liu, R.; Liu, Q.; Meng, H.; Ding, H.; Hao, J.; Ji, Z.; Yue, H.; Wei, W. Org. Chem. Front. 2021, 8, 1970.
[16]
(h) Ye, H.; Xiao, C.; Lu, L. Chin. J. Org. Chem. 2018, 38, 1897. (in Chinese)
[16]
( 叶辉, 肖聪, 陆良秋, 有机化学, 2018, 38, 1897.)
[17]
Crespi, S.; Protti, S.; Fagnoni, M. J. Org. Chem. 2016, 81, 9612.
[18]
Dossena, A.; Sampaolesi, S.; Palmieri, A.; Protti, S.; Fagnoni, M. J. Org. Chem. 2017, 82, 10687.
[19]
Sauer, C.; Liu, Y.; Nisi, A. D.; Protti, S.; Fagnoni, M.; Bandini, M. ChemCatChem 2017, 9, 4456.
[20]
Malacarne, M.; Protti, S.; Fagnoni, M. Adv. Synth. Catal. 2017, 359, 3826.
[21]
Onuigbo, L.; Raviola, C.; Fonzo, A. D.; Protti, S.; Fagnoni, M. Eur. J. Org. Chem. 2018, 2018, 5297.
[22]
Xu, Y. L.; Yang, X. Y.; Fang, H. J. Org. Chem. 2018, 83, 12831.
[23]
(a) Lawrence, D. S.; Copper, J. E.; Smith, C. D. J. Med. Chem. 2001, 44, 594.
[23]
(b) Willardsen, J. A.; Dudley, D. A.; Cody, W. L.; Chi, L.; McClanahan, T. B.; Mertz, T. E.; Potoczak, R. E.; Narasimhan, L. S.; Holland, D. R.; Rapundalo, S. T.; Edmunds, J. J. J. Med. Chem. 2004, 47, 4089.
[23]
(c) Galal, S. A.; Khairat, S. H. M.; Ragab, F. A. F.; Abdelsamie, A. S.; Ali, M. M.; Soliman, S. M.; Mortier, J.; Wolber, G.; El Diwani, H. I. Eur. J. Med. Chem. 2014, 86, 122.
[24]
(a) Yuan, J.; Zhu, J.; Fu, J.; Yang, L.; Xiao, Y.; Mao, P.; Dua, X.; Qu, L. Org. Chem. Front. 2019, 6, 925.
[24]
(b) Wei, W.; Wang, L.; Bao, P.; Shao, Y.; Yue, H.; Yang, D.; Yang, X.; Zhao, X.; Wang, H. Org. Lett. 2018, 20, 7125.
[24]
(d) Meng, N.; Lü, Y.; Liu, Q.; Liu, R.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2021, 32, 258.
[24]
(e) Bao, P.; Liu, F.; Lü, Y.; Yue, H.; Li, J.-S.; Wei, W. Org. Chem. Front. 2020, 7, 492.
[24]
(h) Shi, J.; Wei, W. Chin. J. Org. Chem. 2020, 40, 2170. (in Chinese)
[24]
( 时建伟, 魏伟, 有机化学, 2020, 40, 2170.)
[25]
Jung, H. I.; Lee, J. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2018, 39, 1003.
[26]
Lian, C.; Yue, G. L.; Mao, J. S.; Liu, D. Y.; Ding, Y.; Liu, Z. R.; Qiu, D.; Zhao, X.; Lu, K.; Fagnoni, M.; Protti, S. Org. Lett. 2019, 21, 5187.
[27]
Qiu, D.; Lian, C.; Mao, J. S.; Ding, Y.; Liu, Z. R.; Wei, L. Y.; Fagnoni, M.; Protti, S. Adv. Synth. Catal. 2019, 361, 5239.
[28]
Liu, Q. S.; Wang, L. L.; Yue, H. L.; Li, J. S.; Luo, Z. D.; Wei, W. Green Chem. 2019, 21, 1609.
[29]
(a) Zhang, L.; Niu, C.; Yang, X.; Qin, H.; Yang, J.; Wen, J.; Wang, H. Chin. J. Org. Chem. 2020, 40, 1117. (in Chinese)
[29]
( 张龙菲, 牛聪, 杨晓婷, 秦宏云, 杨建静, 文江伟, 王桦, 有机化学, 2020, 40, 1117.)
[29]
(b) Feng, E.; Hou, Z.; Xu, H. Chin. J. Org. Chem. 2019, 39, 1424. (in Chinese)
[29]
( 冯恩祺, 侯中伟, 徐海超, 有机化学, 2019, 39, 1424.)
[29]
(c) Li, M.; Wang, R.; Hao, W.; Jiang, B. Chin. J. Org. Chem. 2020, 40, 1540. (in Chinese)
[29]
( 李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2019, 39, 1540.)
[29]
(d) Meng, W.; Xu, K.; Guo, B.; Zeng, C. Chin. J. Org. Chem. 2021, 41, 2621. (in Chinese)
[29]
( 孟薇, 徐坤, 郭兵兵, 曾程初, 有机化学, 2021, 41, 2621.)
[29]
(e) Wu, Y.; Chen, J.-Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W.-M. Green Chem. 2021, 23, 3950.
[29]
(f) Chen, J.-Y.; Zhong, C.-T.; Gui, Q.-W.; Zhou, Y.-M.; Fang, Y.-Y.; Liu, K.-J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 475.
[30]
Wang, R. K.; Chen, F. M.; Jiang, L. Q.; Yi, W. B. Adv. Synth. Catal. 2020, 363, 1904.
[31]
(a) Li, Y.; Wan, J.-P. Chin. J. Org. Chem. 2020, 40, 3889. (in Chinese)
[31]
( 李毅, 万结平, 有机化学, 2020, 40, 3889.)
[31]
(b) Liu, Q.; Lü, Y.; Liu, R.; Zhao, X.; Wang, J.; Wei, W. Chin. Chem. Lett. 2021, 32, 136.
[31]
(c) Bao, W.-H.; Wang, Z.; Tang, X.; Zhang, Y.-F.; Tan, J.-X.; Zhu, Q.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2259.
[31]
(d) Lia, G.-H.; Han, Q.-Q.; Sun, Y.-Y.; Chen, D.-M.; Wang, Z.-L.; Xu, X.-M.; Yu, X.-Y. Chin. Chem. Lett. 2020, 31, 3255.
[31]
(e) Wang, L.; Zhang, M.; Zhang, Y.; Liu, Q.; Zhao, X.; Li, J.-S.; Luo, Z.; Wei, W. Chin. Chem. Lett. 2020, 31, 67.
[32]
Wei, W.; Liu, C.; Yang, D.; Wen, J.; You, J.; Suo, Y.; Wang, H. Chem. Commun. 2013, 49, 10239.
[33]
Liu, Q. S.; Liu, F.; Yue, H. L.; Zhao, X. H.; Li, J. S.; Wei, W. Adv. Synth. Catal. 2019, 361, 5277.
[34]
Lü, Y. F.; Liu, Q. S.; Liu, F.; Yue, H. L.; Li, J. S.; Wei, W. Tetrahedron Lett. 2020, 61, 151335.
[35]
Chawla, R.; Jaiswal, S.; Dutta, P. K.; Yadav, L. D. S. Tetrahedron Lett. 2020, 61, 151898.
[36]
Liu, Q. S.; Lü, Y. F.; Liu, R. S.; Zhao, X. H.; Wang, J. W.; Wei, W. Chin. Chem. Lett. 2021, 32, 136.
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