REVIEWS

Radical Cascade Cyclization Involving C(sp3)—H Functionalization of Unactivated Cycloalkanes

  • Rongnan Yi ,
  • Jiaozhe Li ,
  • Dongkai Wang ,
  • Wenting Wei
Expand
  • a Criminal Technology Department, Hunan Police Academy, Changsha 410138
    b School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211

Received date: 2022-08-01

  Revised date: 2022-09-08

  Online published: 2022-09-23

Supported by

Research Project of Education Department of Hunan Province(21A0605); Scientific Research Project of Hunan Police Academy(2021KYQD05)

Abstract

Unactivated cycloalkane is one of the most extensive natural resources, and it is of great significance to develop mild and efficient strategies to achieve C(sp3)—H of unactivated cycloalkanes. At the same time, the preparation of ring compounds is one of the hotspots in organic synthesis and medicinal chemistry. Because of the advantages of mild conditions and high reactivity, radical cascade cyclization involving C(sp3)—H functionalization of unactivated cycloalkanes can simultaneously meet the above requirements and synthesize cyclic molecules with potential applications in high atomic- and step- economy manner. In this review, from the point of view of iron catalysis, copper catalysis, and metal-catalyst-free systems, the advances in radical cascade cyclization involving C(sp3)—H functionalization of unactivated cycloalkanes in recent ten years are summarized.

Cite this article

Rongnan Yi , Jiaozhe Li , Dongkai Wang , Wenting Wei . Radical Cascade Cyclization Involving C(sp3)—H Functionalization of Unactivated Cycloalkanes[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4111 -4121 . DOI: 10.6023/cjoc202208001

References

[1]
Teng, F.; Cheng, J. Chin. J. Chem. 2017, 35, 289.
[2]
(a) Cui, Z.; Shang, X.; Shao, X.-F.; Liu, Z.-Q. Chem. Sci. 2012, 3, 2853.
[2]
(b) Liu, D.; Liu, C.; Li, H.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 4453.
[2]
(c) Tang, R.-Y.; Xie, Y.-X.; Xie, Y.-L.; Xiang, J.-N.; Li, J.-H. Chem. Commun. 2011, 47, 12867.
[2]
(d) Xie, Z.; Cai, Y.; Hu, H.; Lin, C.; Jiang, J.; Chen, Z.; Wang, L.; Pan, Y. Org. Lett. 2013, 15, 4600.
[2]
(e) Xu, Z.; Hang, Z.; Liu, Z.-Q. Org. Lett. 2016, 18, 4470.
[3]
(a) Chen, Z.; Rong, M.-Y.; Nie, J.; Zhu, X.-F.; Shi, B.-F.; Ma, J.-A. Chem. Soc. Rev. 2019, 48, 4921.
[3]
(b) Liu, B.; Romine, A. M.; Rubel, C. Z.; Engle, K. M.; Shi, B.-F. Chem. Rev. 2021, 121, 14957.
[3]
(c) Xue, X.-S.; Ji, P.; Zhou, B.; Cheng, J.-P. Chem. Rev. 2017, 117, 8622.
[3]
(d) Li, J.-Z.; Zhang, W.-K.; Ge, G.-P.; Zheng, H. X. Wei, W.-T. Org. Biomol. Chem. 2021, 19, 7333.
[4]
(a) Daugulis, O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053.
[4]
(b) Davies, H. M.; Manning, J. R. Nature 2008, 451, 417.
[4]
(c) Lapuh, M. I.; Mazeh, S.; Besset, T. ACS Catal. 2020, 10, 12898.
[5]
Xu, Y.; Dong, G. Chem. Sci. 2018, 9, 1424.
[6]
(a) Mondal, S.; Dumur, F.; Gigmes, D.; Sibi, M.; Bertrand, M.; Nechab, M. Chem. Rev. 2022, 122, 5842.
[6]
(b) Péter, á.; Agasti, S.; Knowles, O.; Pyea, E.; Procter, D. Chem. Soc. Rev. 2021, 50, 5349.
[6]
(c) Sumida, Y.; Ohmiya, H. Chem. Soc. Rev. 2021, 50, 6320.
[6]
(d) Tang, C.; Qiu, X.; Cheng, Z.; Jiao, N. Chem. Soc. Rev. 2021, 50, 8067.
[6]
(e) Li, J. B.; Huang, C.-Y.; Li, C.-J. Trends Chem. 2022, 4, 479.
[6]
(f) Huang, C.-Y.; Li, J. B.; Li, C.-J. Nat. Commun. 2021, 12, 4010.
[6]
(g) Huang, C.-Y.; Li, J. B.; Liu, W. B.; Li, C.-J. Chem. Sci. 2019, 10, 5018.
[7]
(a) Li, M.; Li, Y. K.; Jia, W.-Y.; Sun, G.-Q.; Gao, F.; Zhao, G.-X.; Qiu, Y.-F.; Wang, X.-C.; Liang, Y.-M.; Quan, Z.-J. Org. Lett. 2022, 24, 2738.
[7]
(b) Andrew, J. C. Eur. J. Org. Chem. 2016, 2016, 2231.
[7]
(c) Guo, J.; Hao, Y.; Li, G.; Wang, Z.; Liu, Y.; Li, Y.; Wang, Q. Org. Biomol. Chem. 2020, 18, 1994.
[7]
(d) Hu, X.; Tao, M. L.; Ma, Z. X.; Zhang, Y.; Li, Y. N.; Liang, D. Q. Adv. Synth. Catal. 2022, 364, 2163.
[7]
(e) Kong, R.; Fu, T. F.; Yang, R. H.; Chen, D. N.; Liang, D. Q.; Dong, Y.; Li, W. L.; Wang, B. L. ChemCatChem 2021, 13, 2952.
[7]
(f) Li, Y.; Zhang, X.; Liang, D. Q.; Li, Y. N.; Gao, S. L.; Li, X. G.; Dong, Y.; Wang, B. L.; Ma, Y. H. Asian J. Org. Chem. 2021, 10, 642.
[7]
(g) Yang, W.-C.; Wei, K.; Sun, X.; Zhu, J.; Wu, L. Org. Lett. 2018, 20, 3144.
[8]
(a) Zhang, Z. X.; Chen, P. H.; Liu, G. S. Chem. Soc. Rev. 2022, 51, 1640.
[8]
(b) Yi, H.; Zhang, G. T.; Wang, H. M.; Huang, Z. Y.; Wang, J.; Singh, A. K.; Lei, A. W. Chem. Rev. 2017, 117, 9016.
[9]
(a) Nidheesh, P. V. RSC Adv. 2015, 5, 40552.
[9]
(b) Zhang, W.; Luo, M. Chem. Commun. 2016, 52, 2980.
[9]
(c) Lübkena, D.; Saxarraa, M.; Kalesse, M. Synthesis 2019, 51, 161.
[9]
(d) Wang, D.-K.; Li, L.-B.; Liu, F.-L.; Qiu, H.; Li, J.-Z.; Zhang, J.-F.; Deng, C.; Wei, W.-T. ACS Cent. Sci. 2022, 8, 1028.
[10]
(a) Dadashi-Silab, S.; Matyjaszewski, K. Molecules 2020, 25, 1648.
[10]
(b) Kyne, S. H.; Lefèvre, G.; Ollivier, C.; Petit, M.; Claderac, V.-A. R.; Fensterbank, L. Chem. Soc. Rev. 2020, 49, 8501.
[10]
(c) Khan, S.; Baire, B. Chem. Rec. 2021, 21, 3662.
[10]
(d) Wang, J.; Tang, J. J. Mol. Liq. 2021, 332, 115755.
[11]
Qiu, J.-K.; Jiang, B.; Zhu, Y.-L.; Hao, W.-J.; Wang, D.-C.; Sun, J.; Wei, P.; Tu, S.-J.; Li, G. J. Am. Chem. Soc. 2015, 137, 8928.
[12]
Jiang, B.; Li, J.; Pan, Y.; Hao, W.; Li, G.; Tu, S. Chin. J. Chem. 2017, 35, 323.
[13]
Hu, M.; Guo, L.-Y.; Han, Y.; Tan, F.-L.; Song, R.-J.; Li, J.-H. Chem. Commun. 2017, 53, 6081.
[14]
Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
[15]
(a) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968.
[15]
(b) Alagiri, K.; Kumara, G. S.; Prabhu, K. R. Chem. Commun. 2011, 47, 11787.
[15]
(c) Zheng, Y.-N.; Liu, Y.; Cai, X.-E.; Wu, H.-L.; Huang, X.-J.; Liu, Y.-L.; Wei, W.-T. Asian J. Org. Chem. 2022, 11, e202200183.
[16]
Li, Z.; Zhang, Y.; Zhang, L.; Liu, Z.-Q. Org. Lett. 2014, 16, 382.
[17]
Li, Z. J.; Fan, F. H.; Yang, J.; Liu, Z.-Q. Org. Lett. 2014, 16, 3396.
[18]
Liang, D.; Huo, B.; Dong, Y.; Wang, Y.; Dong, Y.; Wang, B.; Ma, Y. Chem. - Asian J. 2019, 14, 1932.
[19]
Ouyang, X.-H.; Song, R.-J.; Liu, B.; Li, J.-H. Chem. Commun. 2016, 52, 2573.
[20]
Ma, D.; Pan, J.; Yin, L.; Xu, P.; Gao, Y.; Yin, Y.; Zhao, Y. Org. Lett. 2018, 20, 3455.
[21]
Xia, D.; Duan, X.-F. Org. Lett. 2021, 23, 2548.
[22]
Xia, D.; Duan, X.-F. Chem. Commun. 2021, 57, 13570.
[23]
Wang, J.; Sang, R.; Chong, X.; Zhao, Y.; Fan, W.; Li, Z.; Zhao, J. Chem. Commun. 2017, 53, 7961.
[24]
Yang, J.-C.; Zhang, J.-J.; Guo, L.-N. Org. Biomol. Chem. 2016, 14, 9806.
[25]
Yadav, A. K.; Yadav, L. D. Org. Biomol. Chem. 2015, 13, 2606.
[26]
(a) Liu, L.; Zhu, Y.-P.; Su, M.; Yuan, Z.-Y. ChemCatChem 2015, 7, 2765.
[26]
(b) Fang, Y.; Wang, X. Angew. Chem., Int. Ed. 2017, 56, 15506.
[26]
(c) Roscales, S.; Csaky, A. G. Chem. Soc. Rev. 2020, 49, 5159.
[27]
(a) Rueping, M.; Dufour, J.; Schoepke, F. R. Green. Chem. 2011, 13, 1084.
[27]
(b) Khan, I.; Zaib, S.; Ibrar, A. Org. Chem. Front. 2020, 7, 3734.
[27]
(c) Yu, X.-C.; Zheng, Y.-N.; Zhang, J.-H.; Zhang, J.; Liu, F.-L.; Tang, K.; Li, T.; Wei, W.-T. ACS Sustainable Chem. Eng. 2022, 10, 6057.
[27]
(d) Li, L.; Li, J.-Z.; Sun, Y. B.; Luo, C. M.; Qiu, H.; Tang, K.; Liu, H.; Wei, W.-T. Org. Lett. 2022, 24, 4704.
[28]
Zhang, H.; Gu, Z.; Xu, P.; Hu, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2016, 52, 477.
[29]
Qian, P.; Du, B.; Jiao, W.; Mei, H.; Han, J.; Pan, Y. Beilstein J. Org. Chem. 2016, 12, 301.
[30]
Xia, W.-J.; Xin, Y.; Zhao, Z.-W.; Chen, X.; Wang, X.-X.; Li, Y.; Wang, G.; Li, Y.-M. Org. Chem. Front. 2020, 7, 1997.
[31]
Li, J.-Z.; Mei, L.; Cai, X.-E.; Zhang, C.-C.; Cao, T.-T.; Huang, X.-J.; Liu, Y.-L.; Wei, W.-T. Adv. Synth. Catal. 2022, 364, 2080.
[32]
Ji, L.; Deng, Q.; Liu, P.; Sun, P. Org. Biomol. Chem. 2019, 17, 7715.
[33]
Zhang, W.-K.; Li, J.-Z.; Zhang, C.-C.; Zhang, J.; Zheng, Y.-N.; Hu, Y.; Li, T.; Wei, W.-T. Eur. J. Org. Chem. 2022, 35, e202200523.
[34]
Shao, L.; Xue, D.; Xue, Y.; Yu, H. Synthesis 2018, 51, 874.
[35]
Sha, W.; Yu, J. T.; Jiang, Y.; Yang, H.; Cheng, J. Chem. Commun. 2014, 50, 9179.
[36]
Pan, C.; Huang, B.; Hu, W.; Feng, X.; Yu, J. T. J. Org. Chem. 2016, 81, 2087.
Outlines

/