Skip to main content
SpringerLink
Log in

Selective Reductive Transformations of Organic Nitro Compounds in Heterogeneous Photocatalytic Systems: A Review

  • Published:
Theoretical and Experimental Chemistry Aims and scope

The cutting-edge research on the photocatalytic selective reductive transformations of organic nitro compounds in heterogeneous systems on the basis of semiconductors of different nature, composites based on them, plasmonic photocatalysts, and other materials is considered. The reactions leading to amines, azo and azoxy compounds, imines, products of N-alkylation, N-formylation, as well as cyclization of quinolines, hydroquinolines, benzimidazoles, and indazoles, are analyzed. Possible ways of further research of selective photocatalysis are outlined.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.
Fig. 9.
Fig. 10.
Fig. 11.
Fig. 12.
Fig. 13.
Fig. 14.

Similar content being viewed by others

References

  1. B. E. Berkmak, Industrial Synthesis of Aromatic Nitro Compounds and Amines, [In Russian], Moscow, Khimiya, (1964).

    Google Scholar 

  2. T. Wirtanen, E. Rodrigo, and S. R. Waldvogel, Adv. Synth. Catal., 362, No. 11, 2088-2101 (2020).

    Article  Google Scholar 

  3. M. Valenzuela, E. Albiter, O. Rios-Berny, et al., J. Adv. Oxid. Technol., 3, No. 3, 321 (2010).

    Google Scholar 

  4. C. Han, S. Liu, Z.-R. Tang, and Y.-J. Xu, Curr. Org. Chem., 19, No. 6 , 484-497 (2015), https://doi.org/10.2174/1385272819666150115000922.

    Article  CAS  Google Scholar 

  5. X. Lang, X. Chen, and J. Zhao, Chem. Soc. Rev., 43, No. 1, 473-486 (2014), https://doi.org/10.1039/C3CS60188A.

    Article  CAS  PubMed  Google Scholar 

  6. J. Kou, C. Lu, J. Wang, et al., Chem. Rev., 117, No. 3, 1445-1517 (2017), https://doi.org/10.1021/acs.chemrev.6b00396.

    Article  CAS  PubMed  Google Scholar 

  7. J. Z. Bloh and R. Marschall, Eur. J. Org. Chem., No. 15, 2085-2094 (2017), https://doi.org/10.1002/ejoc.201601591.

  8. D. Friedmann, H. Hakki, H. Kim, et al., Green Chem., 18, No. 20, 5391-5411 (2016), https://doi.org/10.1039/C6GC01582D.

    Article  CAS  Google Scholar 

  9. Y. Shiraishi and T. Hirai, J. Photochem. Photobiol. C, No. 4, 157-170 (2008), https://doi.org/10.1016/j.jphotochemrev.2008.05.001.

  10. Y. Shiraishi and T. Hirai, J. Jpn. Petrol. Inst., 55, No. 5, 287-298 (2012), https://doi.org/10.1627/jpi.55.287.

    Article  CAS  Google Scholar 

  11. D. Ma, S. Zhai, Y. Wang, et al., Molecules, 24, No. 2, E330 (2019), https://doi.org/10.3390/molecules24020330.

  12. H. Miyabe and S.Kohtani, Sci. China Chem., 62, No. 11, 1439-1449 (2019), https://doi.org/10.1007/s11426-019-9626-9.

    Article  CAS  Google Scholar 

  13. M. Nasrollahzadeh, Z. Nezafat, M. G. Gorab, and M. Sajjadi, Mol. Catal., 484, 110758 (2020).

    Article  Google Scholar 

  14. Q. Xiao, E. Jaatinen, and H. Zhu, Chem. Asian J., 9, No. 11, 3046-3064 (2014), https://doi.org/10.1002/asia.201402310.

    Article  CAS  PubMed  Google Scholar 

  15. S. Sarina, E. R. Waclawik, and H. Zhu, Green Chem., 15, No. 7, 1814-1833 (2013), https://doi.org/10.1039/C3GC4045.

    Article  CAS  Google Scholar 

  16. H. Hao, L. Zhang, W. Wang, and S. Zeng, Catal. Sci. Technol., 8 , No. 5, 1229-1250 (2018), https://doi.org/10.1039/C3GC4045.

    Article  CAS  Google Scholar 

  17. S. Liu, N. Zhang, and Y.-J. Xu, Part. Part. Syst. Charact., 31, No. 5, 540-556 (2014), https://doi.org/10.1002/ppsc.201300235.

    Article  CAS  Google Scholar 

  18. J. Song, Z.-F. Huang, L. Pan, et al., Appl. Catal. B, 227, 386-408 (2018), https://doi.org/10.1016/j.apcatb.2018.01.052.

    Article  CAS  Google Scholar 

  19. J. L. Ferry and W. H. Glaze, Langmuir, 14, No. 13, 3551-3555 (1998).

    Article  CAS  Google Scholar 

  20. S. O. Flores, O. Rios-Bernij, M. A. Valenzuela, et al., Top. Catal., 44, No. 4, 507-511 (2007), 1022-5528/07/0700–0507/0.

  21. F. Mahdavi, T. C. Bruton, and Y. Li, J. Org. Chem., 58, No. 3, 744-746 (1993), https://doi.org/10.1021/jo00055a033.

    Article  CAS  Google Scholar 

  22. O. Rios-Berny, S. O. Flores, I. Cordova, and M. A. Valenzuela, Tetrahedron Lett., 51, No. 20, 2730-2733 (2010), https://doi.org/10.1016/j.tetlet.2010.03.054.

    Article  CAS  Google Scholar 

  23. Z. Zand, F. Kazemi, and S. Hosseini, Tetrahedron Lett., 55, No. 2, 338-341 (2014), https://doi.org/10.1016/j.tetlet.2013.11.023.

    Article  CAS  Google Scholar 

  24. V. Brezova, A. Blazkova, I. Surina, and B. Havlinova, J. Photochem. Photobiol. A, 107, 233-237 (1997), https://doi.org/10.1016/S1010-6030(96)04577-7.

    Article  CAS  Google Scholar 

  25. J. Kaur and B. Pal, Catal. Commun., 53, 25-28 (2014), https://doi.org/10.1016/j.catcom.2014.04.019.

    Article  CAS  Google Scholar 

  26. J. Kaur, S. Singh, and P. Pal, J. Mol. Catal. A, 397, 99-105 (2015), https://doi.org/10.1016/j.molcata.2014.11.007.

    Article  CAS  Google Scholar 

  27. W. Wu, L. Wen, L. Shen, et al., Appl. Catal. B, 130-131, 163-167 (2013), https://doi.org/10.1016/j.apcatb.2012.10.025.

    Article  CAS  Google Scholar 

  28. Y. Shiraishi, Y. Togawa, D. Tsukamoto, et al., ACS Catal., 2, No. 12, 2475-2481 (2012), https://doi.org/10.1021/cs300500p.

    Article  CAS  Google Scholar 

  29. Y. Shiraishi, H. Hirakawa, Y. Togawa, et al., ACS Catal., 3, No. 10, 2318-2326 (2013), https://doi.org/10.1021/cs400532p.

    Article  CAS  Google Scholar 

  30. K. Imamura, T. Yoshikawa, K. Hashimoto, and H. Kominami, Appl. Catal. B, 134-135, 193-197 (2013), https://doi.org/10.1016/j.apcatb.2013.01.015.

    Article  CAS  Google Scholar 

  31. A. Hakki, R. Dillert, and D. W. Bahnemann, Phys. Chem. Chem. Phys., 15, No. 8 , 2992-3002 (2013), https://doi.org/10.1039/C2CP44153E.

    Article  CAS  PubMed  Google Scholar 

  32. T. Zhang, L. You, and Y. Zhang, Dyes Pigments,6 8 , 95-100 (2006), https://doi.org/10.1016/j.dyepig.2005.01.003.

  33. H. M. El-Hosainy, S. M. El-Sheikh, A. A. Ismail, et al., Catalysts, 8 , No. 12, 641 (2018), https://doi.org/10.3390/catal8120641.

    Article  CAS  Google Scholar 

  34. L. Liu, X. Gu, Z. Ji, et al., J. Phys. Chem. C, 117, No. 36, 18578-18587 (2013), https://doi.org/10.1021/jp4064774.

    Article  CAS  Google Scholar 

  35. S. Challagulla, K. Tarafder, R. Ganesan, and S. Roy, Sci. Reports, 7, No. 1, 8783 (2017), https://doi.org/10.1038/s41598-017-08599-2.

  36. S. Singh, R. Prajapat, R. A. Rather, and B. Pal, Arab. J. Chem., 13, No. 1, 2171-2182 (2020), https://doi.org/10.1016/j.arabjc.2018.04.002.

    Article  CAS  Google Scholar 

  37. T. Zhang, L. You, and Y. Zhang, Dyes Pigments,6 8 , 95-100 (2006), https://doi.org/10.1016/j.dyepig.2005.01.003.

  38. O. Mekasuwandumrong, S. Chaitaworn, and J. Panpranot, Catalysts, 9, No. 4, 329 (2019), https://doi.org/10.3390/catal9040329.

    Article  CAS  Google Scholar 

  39. A. Molinari, M. Mazzanti, and M. Fogagnolo, Catal. Lett., 150, No. 4, 1072-1080 (2020), https://doi.org/10.1007/s10562-019-02993-3.

    Article  CAS  Google Scholar 

  40. H. Kominami, S. Iwasaki, T. Maeda, et al., Chem. Lett., 38, No. 5, 410-411 (2009), https://doi.org/10.1246/cl.2009.410.

    Article  CAS  Google Scholar 

  41. M. Ramdar, F. Kazemi, and B. Kaboudin, Chem. Papers, 71, No. 6 , 1155-1163 (2017), https://doi.org/10.1007/s11696-016-0106-3.

    Article  CAS  Google Scholar 

  42. K. Imamura, K. Hashimoto, and H. Kominami, Chem. Commun., 48, No. 36, 4356-4358 (2012), https://doi.org/10.1039/c2cc31524f.

    Article  CAS  Google Scholar 

  43. K. Imamura, K. Nakanishi, K. Hashimoto, and H. Kominami, Tetrahedron, 70, No. 36, 6134-6139 (2014), https://doi.org/10.1016/j.tet.2014.04.067.

    Article  CAS  Google Scholar 

  44. K. Imamura, S. Iwasaki, and T. Maeda, Phys. Chem. Chem. Phys., 13, No. 11, 5114-5119 (2011), https://doi.org/10.1039/c0cp02279a.

    Article  CAS  PubMed  Google Scholar 

  45. M. Fukui, W. Koshida, A. Tanaka, et al., Appl. Catal. B, 268, 118446 (2020), https://doi.org/10.1016/j.apcatb.2019.118446.

    Article  CAS  Google Scholar 

  46. A. Maldotti, L. Andreotti, A. Molinari, et al., J. Photochem. Photobiol. A, 133, Nos. 1-2, 129-133 (2000), https://doi.org/10.1016/S1010-6030(00)00212-4.

    Article  CAS  Google Scholar 

  47. H. Wang, J. Yan, W. Chang, and Z. Zhang, Catal. Commun., 10, No. 6 , 989-994 (2009), https://doi.org/10.1016/j.catcom.2008.12.045.

    Article  CAS  Google Scholar 

  48. H. Huang, J. Zhou, H. Liu, et al., J. Hazard. Mater., 178, Nos. 1-3, 994-998 (2010), doi: 69. https://doi.org/10.1016/j.jhazmat.2010.02.037.

  49. W.-Y. Ahn, S. A. Sheeley, T. Rajh, and D. M. Cropek, Appl. Catal. B, 74, Nos. 1-2, 103-110 (2007), https://doi.org/10.1016/j.apcatb.2007.01.016.

    Article  CAS  Google Scholar 

  50. O. V. Makarova, T. Rajh, M. C. Thurnauer, et al., Environ. Sci. Technol., 34, No. 22, 4797-4803 (2000), https://doi.org/10.1021/es001109+.

    Article  CAS  Google Scholar 

  51. S. Hosseini and A. Amoozadeh, J. Photochem. Photobiol. A, 364, 516-523 (2018), https://doi.org/10.1016/jophotochem.2018.06.035.

  52. M. A. Kakroudi, F. Kazemi, and B. Kaboudin, RSC Adv., 4, No. 95, 52762-52769 (2014), https://doi.org/10.1039/C4RA08059A.

    Article  CAS  Google Scholar 

  53. Y. Yamamoto, M. Fukui, A. Tanaka, et al., Catal. Sci. Technol., 9, No. 4, 966-973 (2019), https://doi.org/10.1039/C8CY02135J.

    Article  CAS  Google Scholar 

  54. S. Fuldner, R. Mild, H. I. Siegmund, et al., Green Chem., 12, No. 3, 400-406 (2010), https://doi.org/10.1039/B918140G.

    Article  Google Scholar 

  55. Q. Li, Y. Xia, C. Yang, et al., Chem. Eng. J., 349, 287-296 (2018), https://doi.org/10.1016/j.cej.2018.05.094.

    Article  CAS  Google Scholar 

  56. P. Wang, X. Li, J. Fang, et al., Appl. Catal. B, 181, 838-847 (2016), https://doi.org/10.1016/j.apcatb.2015.08.046.

    Article  CAS  Google Scholar 

  57. Z. Hu, Q. Quan, Z. Chen, et al., Photochem. Photobiol. Sci., 17, 51-59 (2018), https://doi.org/10.1039/C7PP00256D.

    Article  CAS  PubMed  Google Scholar 

  58. S. R. Amanchi, K. V. A. Kumar, B. Lakshminarayana, et al., New J. Chem., 43, No. 2, 748-754 (2019), https://doi.org/10.1039/C8NJ05260C.

    Article  CAS  Google Scholar 

  59. C. Xu, Y. Yuan, R. Yuan, and X. Fu, RSC Adv., 3, No. 39, 18002-18008 (2013), https://doi.org/10.1039/C3RA42579G.

    Article  CAS  Google Scholar 

  60. C. Xu, X. He, C. Wang, et al., RSC Adv., 6 , No. 87, 84068-84073 (2016), https://doi.org/10.1039/C6RA17603H.

    Article  CAS  Google Scholar 

  61. X. Pan, M.-Q. Yang, Z.-R. Tang, and Y.-J. Xu, J. Phys. Chem. C, 118, No. 47, 27325-27335 (2014), https://doi.org/10.1021/jp507173a.

    Article  CAS  Google Scholar 

  62. H. Tada, T. Ishida, A. Takao, and S. Ito, Langmuir, 20, No. 19, 7898-7900 (2004), https://doi.org/10.1021/la049167m.

    Article  CAS  PubMed  Google Scholar 

  63. H. Tada, T. Ishida, A. Takao, et al., ChemPhysChem., 6 , No. 8 , 1537-1543 (2005), https://doi.org/10.1002/cphc.200500031.

    Article  CAS  PubMed  Google Scholar 

  64. K. Selvam, H. Sakamoto, Y. Shiraishi, and T. Hirai, New J. Chem., 39, No. 4, 2467-2473 (2015), https://doi.org/10.1039/C4NJ01851F.

    Article  CAS  Google Scholar 

  65. W. Wu, G. Liu, Q. Xie, et al., Green Chem., 14, No. 6 , 1705-1709 (2012), https://doi.org/10.1039/C2GC35231A.

    Article  CAS  Google Scholar 

  66. S. Ya. Kuchmii, S. V., A. I. Kryukov, Theor. Exp. Chem., 25, No. 5, 509-514 (1989).

  67. S. V. Kulik, A. V. Korzhak, S. Ya. Kuchmii, and A. I. Kryukov, Theor. Exp. Chem., 30, No. 4, 171-175 (1994).

  68. A. Hernandez-Gordillo, A. G. Romero, F. Tzompantzi, et al., J. Photochem. Photobiol. A, 257, 44-49 (2013), https://doi.org/10.1016/j.jphotochem.2013.02.016.

    Article  CAS  Google Scholar 

  69. A. Hernandez-Gordillo, P. Acevedo-Pena, M. Bizarro, et al., J. Mater. Sci. Mater. Electron., 29, No. 9, 7345-7355 (2018), https://doi.org/10.1007/s10854-018-8724-x.

    Article  CAS  Google Scholar 

  70. R. Singh and B. Pal, J. Mol. Catal. A, 371, 77-85 (2013), https://doi.org/10.1016/j.molcata.2013.01.024.

    Article  CAS  Google Scholar 

  71. R. Singh and B. Pal, J. Mol. Catal. A, 378, 246-254 (2013), https://doi.org/10.1016/j.molcata.2013.06.017.

    Article  CAS  Google Scholar 

  72. A. A. Safari and F. Kazemi, Chem. Papers, 70, No. 5, 531-537 (2016), https://doi.org/10.1515/chempap-2015-0231.

    Article  CAS  Google Scholar 

  73. P. Eskandari, F. Kazemi, and Z. Zand, J. Photochem. Photobiol. A, 274, 7-12 (2014), https://doi.org/10.1016/j.jphotochem.2013.09.011.

    Article  CAS  Google Scholar 

  74. W. Z. Gao, Y. Xu, Y. Chen, and W. F. Fu, Chem. Commun., 51, No. 67, 13217-13220 (2015), https://doi.org/10.1039/C5CC04030B.

    Article  CAS  Google Scholar 

  75. Z.-Y. Liang, M.-H. Huang, S.-Y. Guo, et al, Catal. Sci. Technol., 9, No. 3, 672-687 (2019), https://doi.org/10.1039/C8CY02283F.

    Article  CAS  Google Scholar 

  76. B. Han, S. Liu, Z.-R. Tang, and Y.-J. Xu, J. Energy Chem., 24, No. 2, 145-156 (2015), https://doi.org/10.1016/S2095-4956(15)60295-9.

    Article  Google Scholar 

  77. W. Han, L. Chen, W. Song, et al., Appl. Catal.B, 236, 212-221 (2018), https://doi.org/10.1016/j.apcatb.2018.05.021.

  78. Z. Chen, S. Liu, M.-Q. Yang, and Y.-J Xu, ACS Appl. Mater. Interfaces, 5, No. 10, 4309-4319 (2013), https://doi.org/10.1021/am4010286.

    Article  CAS  Google Scholar 

  79. S. Liu, Z. Chen, N. Zhang, et al., J. Phys. Chem. C, 117, No. 16, 8251-8261 (2013), https://doi.org/10.1021/jp400550t.

    Article  CAS  Google Scholar 

  80. B. Weng, S. Liu, N. Zhang, et al., J. Catal., 309, 146-155 (2014), https://doi.org/10.1016/j.jcat.2013.09.013.

    Article  CAS  Google Scholar 

  81. S. Liu, B. Weng, Z.-R. Tang, and Y.-J. Xu, Nanoscale, 7, No. 3, 861-866 (2015), https://doi.org/10.1039/C4NR04229H.

    Article  CAS  PubMed  Google Scholar 

  82. C. Han, Z. Chen, N. Zhang, et al., Adv. Funct. Mater., 25, No. 2, 221-229 (2015), https://doi.org/10.1002/adfm.201402443.

    Article  CAS  Google Scholar 

  83. S. Liu, M.-Q. Yang, N. Zhang, and Y.-J. Xu, J. Energy Chem., 23, No. 2, 145-155 (2014), https://doi.org/10.1016/S2095-4956(14)60129-7.

    Article  CAS  Google Scholar 

  84. C. Han, M.-Q. Yang, N. Zhang, and Y.-J. Xu, J. Mater. Chem. A, 2, No. 45, 19156-19166 (2014), https://doi.org/10.1039/C4TA04151H.

    Article  CAS  Google Scholar 

  85. N. Zhang, M.-Q. Yang, Z.-R. Tang, and Y.-J. Xu, ACS Nano, 8, No. 1, 623-633 (2014), https://doi.org/10.1021/nn405242t.

    Article  CAS  PubMed  Google Scholar 

  86. F.-X. Xiao, J. Miao, and B. Liu, J. Am. Chem. Soc., 136,No. 4, 1559-1569 (2014), https://doi.org/10.1021/ja411651e.

    Article  CAS  PubMed  Google Scholar 

  87. W.-C. Peng, Y. Chen, and X.-Y. Li, J. Hazard. Mater., 309, 173-179 (2016), https://doi.org/10.1016/j.jhazmat.2016.02.021.

    Article  CAS  Google Scholar 

  88. H. Wei, H. Jiang, Z. Zheng, et al., Mater. Res. Bull., 48, No. 4, 1352-1356 (2013), https://doi.org/10.1016/j.materresbull.2012.11.070.

    Article  CAS  Google Scholar 

  89. S. Zhang, W. Huang, X. Fu, X. Zheng, et al., Appl. Catal. B, 233, 1-10 (2018), https://doi.org/10.1016/j.apcatb.2018.03.084.

    Article  CAS  Google Scholar 

  90. B. Wang, Z. Deng, and Z. Li, J. Catal., 389, 241-246 (2020), https://doi.org/10.1016/j.jcat.2020.05.041.

    Article  CAS  Google Scholar 

  91. H.-J. Lin, Q.-L. Mo, S. Xu, et al., J. Catal., 391, 485-496 (2020), https://doi.org/10.1016/j.jcat.2020.09.011.

    Article  CAS  Google Scholar 

  92. M.-Q. Yang, B. Weng, and Y.-J. Xu, Langmuir, 29, No. 33, 10549-10558 (2013), https://doi.org/10.1021/la4020493.

    Article  CAS  PubMed  Google Scholar 

  93. L. Yuan, M.-Q. Yang, and Y.-J. Xu, J. Mater. Chem. A, 2, No. 35, 14401-14412 (2014), https://doi.org/10.1039/C4TA02670E.

    Article  CAS  Google Scholar 

  94. B. Ma, Y. Wang, X. Tong, et al., Catal. Sci. Technol., 7, No. 13, 2805-2812 (2017), https://doi.org/10.1039/C7CY00356K.

    Article  CAS  Google Scholar 

  95. M.-H. Huang, Y.-B. Li, T. Li, et al., Chem. Commun., 55, No. 71, 10591-10594 (2019), https://doi.org/10.1039/C9CC04562G.

    Article  CAS  Google Scholar 

  96. G. Xiao, P. Li, Y. Zhao, et al., Chem. Asian J., 13, No. 15, 1950-1955 (2018), https://doi.org/10.1002/asia.201800515.

    Article  CAS  Google Scholar 

  97. M. Zheng, T. Yuan, J. Shi, et al., ACS Catal., 9, No. 9, 8068-8072 (2019), https://doi.org/10.1021/acscatal.9b02550.

    Article  CAS  Google Scholar 

  98. Y. Markushyna, A. Vulkel, A. Savateev, et al., J. Catal., 380, 186-194 (2019), https://doi.org/10.1016/j.jcat.2019.10.010.

    Article  CAS  Google Scholar 

  99. X. Dai, M. Xie, S. Meng, et al., Appl. Catal. B, 158-159, 382-390 (2014), https://doi.org/10.1016/j.apcatb.2014.04.035.

    Article  CAS  Google Scholar 

  100. W. Chen, Y.-X. Hua, Y. Wang, et al., J. Catal., 349, 8-18 (2017), https://doi.org/10.1016/j.jcat.2017.01.005.

    Article  CAS  Google Scholar 

  101. L. Zhang, X. He, X. Xu, et al., Appl. Catal. B, 203, 1-8 (2017), https://doi.org/10.1016/j.apcatb.2016.10.003.

    Article  CAS  Google Scholar 

  102. P. Sharma and Y. Sasson, Green Chem., 21, No. 2, 261-268 (2019), https://doi.org/10.1039/C8GC02221F.

    Article  CAS  Google Scholar 

  103. P. Sharma and Y. Sasson, Catal. Commun., 102, 48-52 (2017), https://doi.org/10.1016/j.catcom.2017.08.019.

    Article  CAS  Google Scholar 

  104. A. Kumar, P. Kumar, C. Joshi, et al., Nanomaterials, 6 , No. 4, 59 (2016), https://doi.org/10.3390/nano6040059.

  105. D. V. Thuan, N. T. Khoa, S.-W. Kim, et al., Catal. Lett., 147, No. 9, 2440-2447 (2017), https://doi.org/10.1007/s10562-017-2142-1.

    Article  CAS  Google Scholar 

  106. P. Roy, A. P. Periasamy, C.-T. Liang, and H.-T. Chang, Environ. Sci. Technol., 47, No. 12, 6688-6695 (2013), 6688-6695. https://doi.org/10.1021/es400422k.

  107. S. H. Ahmed, M. Bakiro, F. I. A. Aljasmi, et al., Mol. Catal., 486, 110874 (2020), https://doi.org/10.1016/j.mcat.2020.110874.

    Article  CAS  Google Scholar 

  108. X. Li, C. Wang, B. Li, et al., Phys. Chem. Chem. Phys., 18, No. 40, 27848-27857 (2016), https://doi.org/10.1039/c6cp04929.

    Article  CAS  PubMed  Google Scholar 

  109. S. Fuldner, P. Pohla, H. Bartling, et al., Green Chem., 13, No. 3, 640-643 (2011), https://doi.org/10.1039/C0GC00857E.

    Article  Google Scholar 

  110. Y. Xie, X. Shang, D. Liu, et al., Appl. Catal. B, 259, 118087 (2019), https://doi.org/10.1016/j.apcatb.2019.118087.

    Article  CAS  Google Scholar 

  111. J. Yang, X. Wang, X. Zhao, et al., J. Phys. Chem. C, 119, No. 6 , 3068-3078 (2015), https://doi.org/10.1021/jp510041x.

    Article  CAS  Google Scholar 

  112. E. K. Piggott, T. O. Hope, B. W. Crabbe, et al., Catal. Sci. Technol., 7, No. 23, 5758-5765 (2017), https://doi.org/10.1039/C7CY01820G.

    Article  CAS  Google Scholar 

  113. J. Wang, Z. Ge, L. Pei, et al., Catal. Sci. Technol., 9, No. 23, 6681-6690 (2019), https://doi.org/10.1039/C9CY01257E.

    Article  Google Scholar 

  114. W. Wu, S. Liang, Y. Chen, et al., Catal. Commun., 39-42 (2012), https://doi.org/10.1016/j.catcom.2011.10.012.

  115. W. Wu, G. Liu, S. Liang, et al., J. Catal., 290, 13-17 (2012), https://doi.org/10.1016/j.jcat.2012.02.005.

    Article  CAS  Google Scholar 

  116. A. Tanaka, Y., S., et al., Chem. Commun., 49, No. 25, 2551-2553 (2013), https://doi.org/10.1039/C3CC39096A.

  117. Q. Xiao, S. Sarina, E. R. Waclawik, et al., ACS Catal., 6 , No. 3, 1744-1753 (2016), https://doi.org/10.1021/acscatal.5b02643.

    Article  CAS  Google Scholar 

  118. P. Verma, Y. Kuwahara, K. Mori, and H. Yamashita, Catal. Today, 355, 620-626 (2020), https://doi.org/10.1016/j.cattod.2019.03.058.

    Article  CAS  Google Scholar 

  119. J. Wu, J. Wang, T. Wang, et al., Appl. Surf. Sci., 466, 342-351 (2019), https://doi.org/10.1016/j.apsusc.2018.09.222.

    Article  CAS  Google Scholar 

  120. P. Verma, Y. Kuwahara, K. Mori, and H. Yamashita, Catal. Sci. Technol., 7, No. 12, 2551-2558 (2017), https://doi.org/10.1039/C7CY00321H.

    Article  CAS  Google Scholar 

  121. Ken Tsutsumi, Fumito Uchikawa, Kentaro Sakai, and Kenji Tabata, ACS Catal., 6 , No. 7, 4394-4398 (2016), https://doi.org/10.1021/acscatal.6b00886.

    Article  CAS  Google Scholar 

  122. R. Liang, F. Jing, G. Yan, and L. Wu, Appl. Catal. B, 218, 452-459 (2017), https://doi.org/10.1016/j.apcatb.2017.06.075.

    Article  CAS  Google Scholar 

  123. Y. Dai, C. Li, Y. Shen, et al., Nat. Commun., 9, 60 (2018), https://doi.org/10.1038/s41467-017-02527-8.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  124. B. Pal, T. Torimoto, K.-I. Okazaki, and B. Ohtani, Chem. Commun., 5, No. 5, 483-485 (2007), https://doi.org/10.1039/B616178B.

    Article  Google Scholar 

  125. X. Ke, X. Zhang, J. Zhao, et al., Green Chem., 15, No. 1, 236-244 (2013), https://doi.org/10.1039/C2GC36542A.

    Article  CAS  Google Scholar 

  126. H. Y. Zhu, X. B. Ke, X. Z. Yang, et al., Angew. Chem. Int. Ed., 49, No. 50, 9657-9661 (2010), https://doi.org/10.1002/anie.201003908.

    Article  CAS  Google Scholar 

  127. Z. Liu, Y. Huang, Q. Xiao, and H. Zhu, Green Chem., 18, No. 3, 817-825 (2016), https://doi.org/10.1039/C5GC01726B.

    Article  CAS  Google Scholar 

  128. Q. Xiao, Z. Liu, F. Wang, et al., Appl. Catal. B, 209, 69-79 (2017), https://doi.org/10.1016/j.apcatb.2017.03.002.

    Article  CAS  Google Scholar 

  129. X. Guo, C. Hao, G. Jin, et al., Angew. Chem. Int. Ed., 53, No. 7, 1973-1977 (2014), https://doi.org/10.1002/anie.201309482.

    Article  CAS  Google Scholar 

  130. S. Peiris, S. Sarina, C. Han, et al., Dalton Trans., 46, No. 32, 10665-10672 (2017), https://doi.org/10.1039/C7DT00418D.

    Article  CAS  PubMed  Google Scholar 

  131. G.-J. Chen, W.-L. Xin, J.-S. Wang, et al., Chem. Commun., 55, No. 25, 3586-3589 (2019), https://doi.org/10.1039/C8CC10078K.

    Article  CAS  Google Scholar 

  132. H. Hirakawa, M. Katayama, Y. Shiraishi, et al., ACS Appl. Mater. Interfaces, 7, No. 6 , 3797-3806 (2015), https://doi.org/10.1021/am508769x.

    Article  CAS  PubMed  Google Scholar 

  133. H. Cheng, X. Long, F. Bian, et al., J. Catal., 389, 121-131 (2020), https://doi.org/10.1016/j.jcat.2020.05.033.

    Article  CAS  Google Scholar 

  134. B. Ohtani, H. Osaki, S. Nishimoto, and T. Kagiya, J. Am. Chem. Soc., 108, No. 2, 308-310 (1986), https://doi.org/10.1021/ja00262a028.

    Article  CAS  Google Scholar 

  135. A. Hakki, R. Dillert, and D. Bahnemann, Catal. Today, 144, Nos. 1-2, 154-159 (2009), https://doi.org/10.1016/j.cattod.2009.01.029.

    Article  CAS  Google Scholar 

  136. A. Hakki, R. Dillert, and D. Bahnemann, ACS Catal., 3, No. 4, 565-572 (2013), https://doi.org/10.1021/cs300736x.

    Article  CAS  Google Scholar 

  137. K. H. Park, H. S. Joo, K. Ahn, and K. Jun, Tetrahedron Lett., 36, No. 33, 5943-5946 (1995), https://doi.org/10.1016/0040-4039(95)01204-U.

  138. K. Selvam and M. Swaminathan, Arab. J. Chem., 10, Suppl. 1, S28-S34 (2017), https://doi.org/10.1016/j.arabjc.2012.07.001.

  139. K. Selvam and M. Swaminathan, Bull. Chem. Soc. Jpn., 84, No. 9, 953-959 (2011), https://doi.org/10.1246/bcsj.20110091.

    Article  CAS  Google Scholar 

  140. K. Selvam and M. Swaminathan, J. Mol. Catal. A, 351, 52-61 (2011), https://doi.org/10.1016/j.molcata.2011.09.014.

    Article  CAS  Google Scholar 

  141. K. Selvam and M. Swaminathan, Catal. Commun., 12, No. 6 , 389-393 (2011), https://doi.org/10.1016/j.catcom.2010.11.004.

    Article  CAS  Google Scholar 

  142. K. Selvam and M. Swaminathan, RSC Adv., 2, No. 7, 2848-2855 (2012), https://doi.org/10.1039/C2RA01178F.

    Article  CAS  Google Scholar 

  143. H. Wang, R. E. Partch, and Y. Li, J. Org. Chem., 62, No. 15, 5222-5225 (1997), https://doi.org/10.1021/jo970253j.

    Article  CAS  Google Scholar 

  144. M. Annadhasan, K. Selvam, and M. Swaminathan, Synth. Commun., 42, No. 10, 1500-1508 (2012), https://doi.org/10.1080/00397911.2010.541587.

    Article  CAS  Google Scholar 

  145. K. Selvam and M. Swaminathan, Tetrahedron Lett., 52, No. 26, 3386-3392 (2011), https://doi.org/10.1016/j.tetlet.2011.04.090.

    Article  CAS  Google Scholar 

  146. K. Selvam, B. Krishnakumar, R. Velmurugan, and M. Swaminathan, Catal. Commun., 11, No. 4, 280-284 (2009), https://doi.org/10.1016/j.catcom.2009.10.015.

    Article  CAS  Google Scholar 

  147. J. Patzsch, B. Berg, and J. Z. Bloh, Front. Chem., 7, 289 (2019), https://doi.org/10.3389/fchem.2019.00289.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. L. V. Pysarzhevsky Institute of Physical Chemistry, NAS of Ukraine, Kyiv, Ukraine

    S. Ya. Kuchmiy & O. L. Stroyuk

  2. Forschungszentrum Jülich GmbH, Helmholtz-Institut Erlangen Nürnberg fur Erneuerbare Energien (HI ERN), Erlangen, Germany

    O. L. Stroyuk

Authors
  1. S. Ya. Kuchmiy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. L. Stroyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. Ya. Kuchmiy.

Additional information

Translated from Teoretychna ta Eksperymentalna Khimiya, Vol. 57, No. 1, pp. 3-25, January-February, 2021.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kuchmiy, S.Y., Stroyuk, O.L. Selective Reductive Transformations of Organic Nitro Compounds in Heterogeneous Photocatalytic Systems: A Review. Theor Exp Chem 57, 1–29 (2021). https://doi.org/10.1007/s11237-021-09673-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11237-021-09673-7

Keywords

Search

Navigation