Research Advances on Radical Reactions in Aqueous Phase

doi:10.6023/cjoc202512028

Abstract

Free radicals always serve as significant reaction intermediates for constructing complex molecular frameworks,which characterized by high reactivity and special selectivity in organic synthesis. However,traditional radical reactions heavily rely on toxic,volatile and inflammable organic solvents. Meanwhile,taking advantage of the properties of water,such as non-toxic,non-flammable,cheap,accessible and eco-friendly,developing aqueous phase radical reactions offers an excellent solution to overcome these limitations. The above is the frontier focus in green chemistry currently. This review mainly summarizes the research advances on radical reactions in aqueous phase between 2020 and 2025, which are categorized into: (1)C-H /C-C bond oxidation reactions; (2) coupling reactions; (3) radical additions to alkenes/alkynes; (4) other reactions.

Key words: aqueous reactions, radicals, green chemistry

Cite this article

Xiaoman Wang, Ze Wang, Jie Wu, Yi Hu, Shengqing Ye. Research Advances on Radical Reactions in Aqueous Phase[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202512028.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Gomberg, M. J. Am. Chem. Soc.1900, 22, 757.
[2] Yan M.; Lo J. C.; Edwards J. T.; Baran, P. S. J. Am. Chem. Soc.2016, 138, 12692.
[3] (a) Gao, S.-H.; Qiu, Y.-Y. Sci China Chem, 2016, 59, 1093.
(b) Xia, Q.; Dong, J.-Y.; Song, H.-J.; Wang, Q.-M. Chem. Eur. J. 2019, 25, 2949.
(c) Zhao, J.-P.; Ding, L.-J.; Wang, P.-C.; Liu, Y.; Huang, M.-J.; Zhou, X.-L.; Lu, M. Adv. Synth. Catal. 2020, 362, 5036.
(d) Hou, L.-Z.; Zhou, Y.-Q.; Yu, H.; Zhan, T.-Y.; Cao, W.-D.; Feng, X.-M. J. Am. Chem. Soc. 2022, 144, 22140.
(e) Ren, L.-Q.; Li, N.; Ke, J.; He, C. Org. Chem. Front. 2022, 9, 6400.
(f) Hu, Z.-B.; Cheng, Z.-R.; Jiao, N. Chin. J. Chem. 2024, 42, 1157.
(g) Zhang, J.-H.; Wang, J.-J.; Cheng, Q. Chin. J. Chem. 2024, 42, 1009.
(h) Xiao, W.; C, J.-Q.; W. J. Chem. Soc. Rev. 2025, 54, 6832.
[4] Nanda B.; Sailu M. S.; Priyaranjan P. M.; Ranjan P. K. P.; Nanda, B. B. Materials Today: Proceedings.2021, 47, 1234.
[5] Anastas P. T.;Warner J. C.Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998.
[6] Breslow, R. Acc. Chem. Res. 1991, 24, 159.
[7] (a) Li, C.-J. Chem. Rev. 1993, 93, 2023.
(b) Lindström, U. M. Chem. Rev. 2002, 102, 2751.
(c) Breslow, R. Acc. Chem. Res. 2004, 37, 471.
(d) Li, C.-J. Chem. Rev. 2005, 105, 3095.
(e) Levin, E.; Ivry, E.; Diesendruck, C. E.; Lemcoff, N.G. Chem. Rev. 2015, 115, 4607.
(f) Sun, K.; Lv, Q.-Y.; Chen, X.-L.; Qu, L.-B.; Yu, B. Green Chem. 2021, 23, 232.
(g) Barata-Vallejo, S.; Yerien, D. E.; Postigo, A. ACS Sustainable Chem. Eng. 2021, 9, 10016.
(h) Russo, C.; Brunelli, F.; Tron, G. C.; Giustiniano, M. J. Org. Chem. 2023, 88, 6284.
(i) Yang, C.-R.; Wang, H.-H.; Xie, P. ChemSusChem. 2025, 18, e202401915.
[8] (a) Li, S.-L.; Zhu, B.; Lee, R.; Qiao, B.-K.; Jiang. Z.-Y. Org. Chem. Front. 2018, 5, 380.
(b) Zhu, X.-J.; Liu, Y.; Liu, C.; Yang, H.-J.; Fu, H. Green Chem. 2020, 22, 4357.
(c) Hosseini-Sarvari, M.; Dehghani, A. New J. Chem. 2020, 44, 16776.
(d) Li, W.-J.; Li, S.; Luo, L.-H.; Ge, Y.-C.; Xu, J.-Q.; Zheng, X.-L.; Yuan, M.-L.; Li, R.- X.; Chen H.; Fu, H.-Y. Green Chem. 2021, 23, 3649.
(e) Zhao, J.-N.; Sun, H.-N.; Lu, Y.; Li, J.-N.; Yu, Z.-Y.; Zhu, H.-F.; Ma, C.-F.; Meng, Q.-W.; Peng, X.-J. Green Chem. 2022, 24, 8503.
[9] Xie P.; Xue C.; Shi S.-S.; Du D.-D. ChemSusChem.2021, 14, 2689.
[10] Bo C.-B.; Bu Q.-Q.; Liu J.-C.; Dai B.; Liu, N. ACS Sustainable Chem. Eng.2022, 10, 1822.
[11] (a) Hirashima, S.-i.; Nobuta, T.; Tada, N.; Miura, T.; Itoh, A. Org. Lett. 2010, 12, 3645.
(b) Nobuta, T.; Fujiya, A.; Hirashima, S.-i.; Tada, N.; Miura, T.; Itoh, A. Tetrahedron Lett. 2012, 53, 5306.
(c) Tripathi, S.; Singh, S. N.; Yadav, L. D. S. RSC Adv. 2016, 6, 14547.
(d) Yunusova, S. N.; Bolotin, D. S.; Vovk, M. A.; Tolstoy, P. M.; Kukushkin, V. Y. Eur. J. Org. Chem. 2020, 2020, 6763.
(e) Kumar, S.; Shah, T. A.; Punniyamurthy, T. Org. Chem. Front. 2021, 8, 4288.
(f) Tu, M.; Chen, B.-J.; Rukhsana, Cui, W.-Y.; Fu, W.-T.; Shen, C.-S.; Shen, Y.-M. New J. Chem. 2022, 46, 23276.
[12] (a) Nishina, Y.; Ohtani, B.; Kikushima, K. Beilstein J. Org. Chem. 2013, 9, 1663.
(b) Talukdar, R. Org. Biomol. Chem. 2020, 18, 8294.
(c) He, X.; Yao, X.-Y.; Cai, S.-F.; Li, H.-R.; He, L.-N. Chem. Commun. 2022, 58, 5845.
[13] Bo C.-B.; Li M.; Chen F.; Liu J.-C.; Dai B.; Liu N. ChemSusChem.2024, 17, e202301015.
[14] (a) Wang A.-Z.; Jiang, H.-F. J. Org. Chem.2010, 75, 2321.
(b) Tang Q.-H.; Wang Y.-Y.; Zhang J.; Qiao R.; Xie X.-P.; Wang Y.; Yang, Y.-H. Appl. Organomet. Chem.2016, 30, 435.
(c) Amaya, T.; Fujimoto, H. Tetrahedron Lett. 2018, 59, 2657.
[15] Xie P.; Xue C.; Luo J.-F.; Shi S.-S.; Du D.-D. Green Chem.2021, 23, 5936.
[16] Zhang Y.-L.; Yue X.-G.; Liang C.-F.; Zhao J.-M.; Yu W.-B.; Zhang P.-F. Tetrahedron Lett.2021, 80, 153321.
[17] (a) Wang, D.-H.; Wang, F.; Chen, P.-H.; Lin, Z.-Y.; Liu, G.-S.Angew. Chem. Int. Ed. 2017, 56, 2054.
(b) Hazra S.; Kaur G.; Handa, S. ACS Sustainable Chem. Eng.2021, 9, 5513.
(c) Shee, M.; Singh, N.D.P. Chem. Soc. Rev. 2022, 51, 2255.
[18] Yue X.-G.; Ouyang Y.-N.; Zhu J.-S.; Yue J.-F.; Peng J.-H.; Li, W.-M. Asian J. Org. Chem.2023, 12, e202300124.
[19] Li, W.-J.; Liu, C.-Y.; Liang, L.-L.; Zhang, J.; Miao, Y.-Q.; Org. Chem. Front. 2024, 11, 5429.
[20] Gu J.-Y.; Yang H.; Deng J.-F.; Jiang D.-B.; Lv K.-Z.; Wang T.; Yao Q.-L.Org. Chem. Front. 2024, 11, 1910.
[21] (a) Song, J. J.; Reeves, J. T.; Gallou, F.; Tan, Z.-L.; Yee, N. K.; Senanayake, C. H. Chem. Soc. Rev. 2007, 36, 1120.
(b) Baraldi, P. G.; Tabrizi, M. A.; Gessi, S.; Borea, P. A. Chem. Rev. 2008, 108, 238.
(c) Archna, Pathania, S.; Chawla, P. A. Bioorg. Chem. 2020, 101, 104026.
(d) Feng, Y.-D.; Zhang, Z.-Y.; Fu, Q.; Yao, Q.-H.; Huang, J.-H.; Shen, H.-B.; Cui, X.-L. Chin. Chem. Lett. 2020, 31, 58.
(e) Yang, H.-Y.; Wang, Y.-F.; Wang, Y.; Zhang, Z.-Y.; Ma, H.-L.; Yamauchi, Y.; Ling, K.-J.; Zhao, Y.; Cai, S.-Z.; An, Z.-F.; Huang, W. Adv. Mater. 2025, 37, e03550.
[22] (a) Matcha, K.; Antonchick, A. P. Angew. Chem. Int. Ed. 2013, 52, 2082.
(b) Garza-Sanchez, R. A.; Tlahuext-Aca, A.; Tavakoli, G.; Glorius, F. ACS Catal. 2017, 7, 4057.
(c) Candish, L.; Freitag, M.; Gensch, T.; Glorius, F. Chem. Sci. 2017, 8, 3618.
(d) Cheng, W.-M.; Shang, R.; Fu, Y. ACS Catal. 2017, 7, 907.
(e) Galloway, J. D.; Mai, D. N.; Baxter, R. D. Org. Lett. 2017, 19, 5772.
[23] (a) Ries, U. J.; Priepke, H. W. M.; Hauel, N. H.; Handschuh, S.; Mihm, G.; Stassen, J. M.; Wienen, W.; Nar, H. Bioorg. Med. Chem. Lett. 2003, 13, 2297.
(b) Liu, R.; Huang, Z.-H.; Murray, M. G.; Guo, X.-Y.; Liu, G. J. Med. Chem. 2011, 54, 5747.
(c) Hussain, S.; Parveen, S.; Hao, X.; Zhang, S.-Z.; Wang, W.; Qin, X.-Y.; Yang, Y.-C.; Chen, X.; Zhu, S.-J.; Zhu, C.-J.; Ma, B. Eur. J. Med. Chem. 2014, 80, 383.
(d) Ke, Q.-M.; Yan, G.-M.; Yu, J.; Wu, X.-M. Org. Biomol. Chem. 2019, 17, 5863.
[24] Gao Y.-H.; Zhao L.-L.; Xiang T.-Y.; Li P.-H.; Wang L. RSC Adv.2020, 10, 10559.
[25] Hong G.-F.; Yuan J.-W.; Fu J.-H.; Pan G.-Y.; Wang Z.-W.; Yang L.-R.; Xiao Y.-M.; Mao P.; Zhang, X.-M. Org. Chem. Front.2019, 6, 1173.
[26] Zhou J.-D.; Ren Q.-L.; Xu N.; Wang C.-D.; Song S.-J.; Chen Z.; Li J.-J. Green Chem.2021, 23, 5753.
[27] Yang Z.-L.; Cao K.; Peng X.-Y.; Lin L.; Fan D.-C.; Li J.-L.; Wang J.-X.; Zhang X.-B.; Jiang H.-Z.; Li J.-H.Chin. J. Chem. 2021, 39, 3347.
[28] Ma C.-H.; Zhao L.; He X.; Jiang Y.-Q.; Yu, B. Org. Chem. Front.2022, 9, 1445.
[29] (a) Jin, J.; MacMillan, D. W. Angew. Chem. Int. Ed. 2015, 54, 1565.
(b) Quattrini, M. C.; Fujii, S.; Yamada, K.; Fukuyama, T.; Ravelli, D.; Fagnoni, M.; Ryu, I. Chem. Commun. 2017, 53, 2335.
(c) Xu, P.; Chen, P.-Y.; Xu, H.-C. Angew. Chem., Int. Ed. 2020, 59, 14275.
(d)Huang, H.; Strater, Z. M.; Lambert, T. H. J. Am. Chem. Soc. 2020, 142, 1698.
(e)Liu, Y.-C.; Shi, B.-Y.; Liu, Z.; Gao, R.-F.; Huang, C.-L.; Alhumade, H.; Wang, S.-C.; Qi, X.-T.; Lei, A.-W. J. Am. Chem. Soc. 2021, 143, 20863.
[30] Yang J.-F.; Liu Y.-F.; Wei L.-L.; Qiao K.-K.; Zhao Y.-Q.; Shi, L. J. Org. Chem.2024, 89, 4249.
[31] Liu A.-D.; Wang Z.-L.; Liu L.; Cheng, L. J. Org. Chem.2021, 86, 16434.
[32] (a) Yi H.; Zhang G.-Y.; Wang H.-M.; Huang Z.-Y.; Wang J.; Singh A. K.; Lei A.-W. Chem. Rev.2017, 117, 9016.
(b) Xie J.; Jin H.-M.; Hashmi, A. S. K. Chem. Soc. Rev.2017, 46, 5193.
(c) Sun, J.-W.; He, J.-Y.; Massaro, L.; Cagan, D. A.; Tsien, J.; Wang, Y.; Attard, F. C.; Smith, J. E.; Lee, J. S.; Kawamata, Y.; Baran, P. S. Nature. 2025, 642, 85.
[33] Xu Y.-W.; Xu X.-Z.; Wu B.; Gan C.-L.; Lin X.-Y.; Wang J.; Ke, F. Asian J. Org. Chem.2020, 9, 1032.
[34] Li X.-H.; Cui W.-W.; Deng Q.-R.; Song X.-Y.; Lv J.; Yang D.-S. Green Chem.2022, 24, 1302.
[35] Zhen J.-S.; Li Y.-H.; Yuan H.; Xu X.-H.; Du X.; Li X.-Q.; Luo, Y. Org. Chem. Front.2023, 10, 404.
[36] Hui X.; Zhang D.; Wu C.-Y.; Ma Y.-F.; Zhou H.-H.; Zhu Y.-B. Green Chem.2023, 25, 2274.
[37] Li M.-F.; Cheng X. Nat Commun.2024, 15, 7540.
[38] (a) Jiang H.; Studer, A. Chem. Soc. Rev.2020, 49, 1790.
(b) Yang H.-F.; Wang Y.-R.; Wang L.-C.; Wu X.-F. EES Catal.2024, 2, 1247.
(c) Ma, B.; Zhao, Z.; Ma, M.; Zhang, R.; Yang, J.-Y. Org. Chem. Front. 2025, 12, 3636., 7681.
(d) Gu, L.-J.; Xu, R.-Y.; Huan, W.-W.; Zhang, Y. Org. Biomol. Chem. 2025, 23, 7681.
[39] Liu J.-K.; Yao H.; Li X.-N.; Wu H.-Y.; Lin A.-J.; Yao H.-Q.; Xu J.-Y.; Xu, S.-T. Org. Chem. Front.2020, 7, 1314.
[40] Lin L.; Yang Z.-L.; Liu J.-C.; Wang J.-X.; Zheng J.-L.; Li J.-L.; Zhang X.-B.; Liu X.-W.; Jiang H.-Z.; Li J.-H. Green Chem.2021, 23, 5467.
[41] Sun B.; Tang X.-L.; Zhuang X.-H.; Ling L.; Huang P.-Y.; Wang J.-Y.; Jin, C. Adv. Synth. Catal.2023, 365, 1020.
[42] Wang Z.-K.; Wang L.-X.; Lin H.; Qiu B.; Ma Y.-C.; Xiao J.; An X.-D. Green Chem.2025, 27, 4565.
[43] Renzi P.; Rusconi M.; Ghigo G.; Deagostinoa A.Adv. Synth. Catal. 2023, 365, 4623.
[44] Zhu B.-F.; Ponnam D.; Li M.-Z.; Li G.-K.; Fan R.-F.; Chen J.-C.; Fan, B.-M. J. Org. Chem.2025, 90, 7738.
[45] Yan K.-C.; He H.; Li J.-L.; Luo Y.; Lai R.-Z.; Guo L.; Wu, Y. Chin. Chem. Lett.2021, 32, 3984.
[46] Xu P.; Huang P.-Y.; Jiang Y.; Lv C.; Li P.-X.; Wang J.-Y.; Sun B.; Jin C. Green Chem.2023, 25, 8741.
[47] (a) Duddeck H.; Bradenahl R.; Stefaniak L.; Jazwinski J.;Kamienski, B. Magn. Reson. Chem.2001, 39, 709.
(b) Liu, J.; Xu, S.-J.; Huang, C.; Shen, J.-T.; Yu, S.; Yu, Y.-Z.; Sun, Q.-Y.; Dai, Q.-Y. Bioorg. Med. Chem. Lett. 2022, 73, 128913.
[48] Hasan C.; Hunter R. F.J. Chem. Soc. 1935, 1762.
[49] Ji H.-T.; Wang K.-L.; Ouyang W.-T.; Luo Q.-X.; Li H.-X.; He W.-M. Green Chem.2023, 25, 7983.
[50] (a) Olack G.; Morrison, H. J. Org. Chem.1991, 56, 4969.
(b) Guanti G.; Banfi L.; Powles K.; Rasparini M.; Scolastico C.; Fossati N. Tetrahedron: Asymmetry.2001, 12, 271.
(c) Christoffers, J.; Werner, T.; Frey, W.; Baro, A. Chem. Eur. J. 2004, 10, 1042.
[51] (a) Liang Y.-F.; Jiao, N. Angew. Chem. Int. Ed.2014, 53, 548.
(b) Chaudhari, M. B.; Sutar, Y.; Malpathak, S.; Hazra, A.; Gnanaprakasam, B. Org. Lett. 2017, 19, 3628.
(c) Wang Y.-T.; Lu R.; Yao J.; Li, H.-R. Angew. Chem. Int. Ed. 2021, 60,6631.
(d) He, Y.-J.; Yin, H.; Wang, Y.-F.; Chu, M.-M.; Li, Y.-M.RSC Adv. 2023, 13, 7843.
[52] Wang Y.; Wang Z.-J.; Luo H.; Wang G.-H.; Shi, Z.-D. Ma Y.-F.; Wu J.-L.; Li D.-J.; Yang, J.-H. Org. Chem. Front.2024, 11, 5524.
[53] (a) Sauer, G. S.; Lin, S. ACS Catal. 2018, 8, 5175.
(b) Xiong, P.; Long, H.; Song, J.-S.; Wang, Y.-H.; Li, J.-F.; Xu, H.-C. J. Am. Chem. Soc. 2018, 140, 16387.
(c) Zhang, W.; Lin, S. J. Am. Chem. Soc. 2020, 142, 20661.
(d) Song, L.; Fu, N.-K.; Ernst, B. G.; Lee, W.-H.; Frederick, M. O.; DiStasio, R. A.; Lin, S. Nat. Chem. 2020, 12, 747.
(e) Siu, J. C.; Fu, N.-K.; Lin, S. Acc. Chem. Res. 2020, 53, 547.
(f) Wang, Y.-L.; Dana, S.; Long, H.; Xu, Y.; Li, Y.-J.; Kaplaneris, N.; Ackermann, L. Chem. Rev. 2023, 123, 11269.
[54] Li M.-F.; Pu T.-F.; Cheng X.Synthesis. 2025, 57, 2063.

水相中的自由基反应研究进展