REVIEWS

Developments in Visible Light Catalyzed Asymmetric Minisci Reactions

  • Wenya Li ,
  • Yu Wang ,
  • Jiangqi Chen ,
  • Dan Shi ,
  • Liang Zhang ,
  • Xiaochun Yu ,
  • Zheng-Jun Wang
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  • a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
    b Wenzhou Market Supervision Administration, Wenzhou Quality and Technical Testing Science Research Institute, Wenzhou, Zhejiang 325052
    c State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082

Received date: 2023-12-16

  Revised date: 2024-02-12

  Online published: 2024-03-28

Supported by

Open Project of State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University(20230767); Basic Scientific Research Projects in Wenzhou City(G20220020)

Abstract

N-Heterocyclic aromatics are among the most prevalent motifs in natural products, pharmaceuticals, and organic materials. Therefore, the selective functionalization of N-heterocyclic aromatics, represented by the Minisci reaction, has always been a hot topic for chemists. Meanwhile, in recent years, photocatalysis has sparked a new research trend as a green, safe, clean, and renewable catalytic method. Although a review has been conducted on photoinduced Minisci reactions in recent years, the exploration of asymmetric Minisci reactions is limited. The research progress on visible-light photocatalytic asymmetric Minisci reactions in recent years from the classification of free radical precursors and different reaction pathways is summarized. Furthermore, prospects for future development are also discussed.

Cite this article

Wenya Li , Yu Wang , Jiangqi Chen , Dan Shi , Liang Zhang , Xiaochun Yu , Zheng-Jun Wang . Developments in Visible Light Catalyzed Asymmetric Minisci Reactions[J]. Chinese Journal of Organic Chemistry, 2024 , 44(7) : 2110 -2123 . DOI: 10.6023/cjoc202312016

References

[1]
Welsch, M. E.; Snyder, S. A.; Stockwell, B. R.; Curr. Opin. Chem. Biol. 2010, 14, 347.
[2]
Bhutani, P.; Joshi, G.; Raja, N.; Bachhav, N.; Rajanna, P. K.; Bhutani, H; Paul, A. T.; Kumar, R. J. Med. Chem. 2021, 64, 2339.
[3]
DiRocco, D. A.; Dykstra, K.; Krska, S.; Vachal, P.; Conway D. V.; Tudge, M. Angew. Chem., Int. Ed. 2014, 53, 4802
[4]
Proctor Rupert, S. J.; Davis, H. J.; Phipps, R. J. Science 2018, 360, 419.
[5]
Antonchick, A. P.; Burgmann, L. Angew. Chem., Int. Ed. 2013, 52, 3267.
[6]
Matcha, K.; Antonchick, A. P.; Burgmann, L. Angew. Chem., Int. Ed. 2013, 52, 2082.
[7]
Siddaraju, Y.; Lamani, M.; Prabhu, K. R. J. Org. Chem. 2014, 79, 3856.
[8]
Minisci, F.; Bernardi, R.; Bertini, F.; Galli, R.; Perchinummo, M. Tetrahedron 1971, 27, 3575.
[9]
Yan, M.; Lo, C. J.; Edwards, T. J.; Baran, S. P. J. Am. Chem. Soc. 2016, 138, 12714.
[10]
Mai, D. N.; Baxter, R. D. Org. Lett. 2016, 18, 3738.
[11]
Murakami, K.; Yamada, S.; Kaneda, T.; Itami, K. Chem. Rev. 2017, 117, 9302.
[12]
Liu, X.-L..; Jiang, L.-B.; Luo, M.-P.; Ren, Z.; Wang, S.-G. Org. Chem. Front. 2022, 9, 265.
[13]
Dong, J.; Lyu, X.; Wang, Z.; Wang, X.; Song, H.; Liu, Y.; Wang, Q. Chem. Sci. 2019, 10, 976.
[14]
Zhidkov, M. E.; Kaminskii, V. A. Tetrahedron Lett. 2013, 54, 3530.
[15]
Jin, J.; Macmillan, D. W. C. Angew. Chem., Int. Ed. 2014, 54, 1565.
[16]
Liang, X.-A.; Niu, L.; Wang, S.; Liu, J.; Lei, A. Org. Lett. 2019, 21, 2441.
[17]
Chen, H.; Fan, W.; Yuan, X.-A.; Yu, S. Nat. Commun. 2019, 10, 4743.
[18]
Ji, X.; Liu, Q.; Wang, Z.; Wang, P.; Deng, G.-J.; Huang, H. Green Chem. 2020, 22, 8233.
[19]
Pan, Z.-T.; Shen, L-M.; Dagnaw, F. W.; Zhong, J.-J.; Jian, J.-X.; Tong, Q.-X. Chem. Commun. 2023, 59, 1637.
[20]
Gao, Y.-Y.; Wu, Z.-G.; Yu, L.; Wang, Y.; Pan, Y. Angew. Chem., Int. Ed. 2020, 59, 10859.
[21]
Río-Rodríguez, R. D.; Fragoso-Jarillo, L.; Garrido-Castro, A. F.; Maestro, M. C.; Fernández-Salas, J. A.; Alemán, J. Chem. Sci. 2022, 13, 6512.
[22]
Mo, Y.-M.; Lu, Z.-H.; Rughoobur, G.; Patil, P.; Gershenfeld, N.; Akinwande, A. I.; Buchwald, S. L.; Jensen, K. F. Science 2020, 368, 1352.
[23]
Wang, P.; Yang, Z.-L.; Wang, Z.-W.; Xu, C.-Y.; Huang, L.; Wang, S.-C.; Zhang, H.; Lei, A.-W. Angew. Chem., Int. Ed. 2019, 58, 15747.
[24]
Ding, H.; Xu, K.; Zeng, C.-C. J. Catal. 2020, 381, 38.
[25]
Xu, P.; Chen, P.-Y.; Xu, H.-C. Angew. Chem., Int. Ed. 2020, 59, 14275.
[26]
Tan, Z.; He, X.; Xu, K.; Zeng, C. ChemSusChem 2022, 15, e2021023.
[27]
Wang, Z.-J.; Zheng, S.; Matsui, J. K.; Lu, Z.-P.; Molander, G. A. Chem. Sci. 2019, 10, 4389.
[28]
Li, D.-S.; Liu, T.; Hong, Y.; Cao, C.-L.; Wu, J.; Deng, H.-P. ACS Catal. 2022, 12, 4473.
[29]
Calcaterra, A.; D’Acquarica, I. J. Pharm. Biomed. Anal. 2018, 147, 323.
[30]
Leonori, L. D.; Aggarwal, V. K. J. Am. Chem. Soc. 2015, 137, 10958.
[31]
Zuo, Z.; Cong, H.; Li, W.; Choi, J.; Fu, G. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 1832.
[32]
Baco?, P. D.; Lahdenper?, A. S. K.; Phipps, R. J. Acc. Chem. Res. 2023, 56, 2037.
[33]
Jin, J.; MacMillan, D. W. C. Nature 2015, 525, 87.
[34]
Jin, J.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 1565.
[35]
Zheng, D.; Studer, A. Angew. Chem., Int. Ed. 2019, 58, 15803.
[36]
Garza-Sanchez, R. A.; Tlahuext-Aca, A.; Tavakoli, G.; Glorius, F. ACS Catal. 2017, 7, 4057.
[37]
Li, G. X.; Morales-Rivera, C. A.; Wang, Y.; Gao, F.; He, G.; Liu, P.; Chen, G. Chem. Sci. 2016, 7, 6407.
[38]
Dong, J.; Wang, X.; Song, H.; Liu, Y.; Wang, Q. Adv. Synth. Catal. 2020, 362, 2155.
[39]
Cheng, W.-M.; Shang, R.; Fu, Y. ACS Catal. 2017, 7, 907.
[40]
Rupert, S. J.; Davis, H. J.; Phipps, R. J. Science 2018, 360, 419.
[41]
Liu, X.; Liu, Y.; Chai, G.; Qiao, B.; Zhao, X.; Jiang, Z. Org. Lett. 2018, 20, 6298.
[42]
Reid, J. P.; Rupert, S. J.; Sigman, M. S.; Phipps, R. J. J. Am. Chem. Soc. 2019, 141, 19178.
[43]
Fu, M.-C.; Shang, R.; Zhao, B.; Wang, B.; Fu, Y. Science 2019, 363, 1429.
[44]
Guo, J.; Xie, Y.; Lai, Z. -M.; Weng, J.; Chan, A. S. C.; Lu, G. ACS Catal. 2022, 12, 13065.
[45]
Liang, D.; Chen, J.-R.; Tan, L.-P.; He, Z.-W.; Xiao, W.-J. J. Am. Chem. Soc. 2022, 144, 6040.
[46]
Liang, D.; Xiao, W. J.; Lakhdar, S.; Chen, J. O. Green Synth. Catal. 2022, 3, 212.
[47]
Luo, M.-P.; Gua, Y.-J.; Wang, S.-G. Chem. Sci. 2023, 14, 251.
[48]
Huang, C.-Y.; Li, J.; Liu, W.; Li, C.-J. Chem. Sci. 2019, 10, 5018.
[49]
Rupert, S. J.; Chuentragool, P.; Colgan, A. C.; Phipps, R. J. J. Am. Chem. Soc. 2021, 143, 4928.
[50]
Li, C.; Chen, B.; Ma, X. D.; Mo, X. L.; Zhang, G. Z. Angew. Chem., Int. Ed. 2020, 60, 2130.
[51]
Niu, L.-B.; Liu, J.-M.; Liang, X.-A.; Wang, S.-C.; Lei, A.-W. Nat. Commun. 2019, 10, 467.
[52]
Colgan, A. C.; Rupert, S. J.; Gibson, D. C.; Chuentragool, P.; Lahdenper?, A. S. K.; Ermanis, K.; Phipps, R. J. Angew. Chem., Int. Ed. 2022, 61, e202200266.
[53]
Zheng, D. Q.; Studer, A. Angew. Chem., Int. Ed. 2019, 58, 15803.
[54]
Ma, C. R.; Shen, J. Y.; Qu, C. F.; Shao, T. J.; Cao, S. S.; Yin, Y. L.; Zhao, X. W.; Jiang, Z. Y. J. Am. Chem. Soc. 2023, 145, 36, 20141.
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