Citation: Shehla Khalid, Muhammad Bilal, Nasir Rasool, Muhammad Imran. Photochemical reactions as synthetic tool for pharmaceutical industries[J]. Chinese Chemical Letters, ;2024, 35(9): 109498. doi: 10.1016/j.cclet.2024.109498 shu

Photochemical reactions as synthetic tool for pharmaceutical industries

a.
Department of Chemistry, Government College University, Faisalabad 38000, Pakistan
b.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China
c.
Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia

Author Bio: Shehla Khalid received her Bachelor's degree from Government College University, Faisalabad. She completed her master's degree under the supervision of Prof. Nasir Rasool from the same institute. Her research interest focuses on transition metal catalyzed reactions, chemistry of heterocycles, photo/electrochemical reactions, bio-active molecules synthesis, coupling reactions, inert bonds activation and functionalization
Muhammad Bilal received his Bachelor's and Master's degrees from Government College University, Faisalabad, under the supervision of Prof. Nasir Rasool. Then, he joined Higher Education Department Pakistan as a Lecturer of Chemistry. Now, he is doing Ph.D. as a CSC fellow under the supervision of Prof. Yu-Feng Liang at Shandong University, China. Currently, his doctoral research focuses on cross coupling reactions using electrochemistry or earth-abundant transition metals and ring-opening reactions
Nasir Rasool was born in Chichawatni, Sahiwal, Pakistan. He received his MSc. degree from Bahauddin Zakariya University Multan. Later he joined Prof Dr Peter Langer at the institute of Chemistry, University of Rostock, Germany as PhD research fellow. Then he joined Government College University Faisalabad as an Assistant Professor. He has published more than 200 research articles and supervised number of graduate, post graduate and PhD students. He received research productivity awards from Pakistan council of science and technology several times. His-current research focuses on synthesis of small drug molecules, cross-coupling reactions and synthesis of organic solar cells and theoretical studies. Now, he is working as a Professor of Chemistry at Department of Chemistry GC University, Faisalabad, Pakistan
Muhammad Imran completed his graduation in Chemistry from the University of Agriculture, Faisalabad, Pakistan and obtained his PhD degree from International Center for Chemical and Biological Science, University of Karachi, Pakistan in 2009. Then he joined Higher Education Department Lahore, Pakistan as Assistant Professor in 2009. He worked as a post-doc researcher at University of Sao Paulo Brazil in 2011 and at University of Bristol UK in 2017. His-research interest focused on biologically active natural, synthetic products, functional nanomaterials, and first principle investigations. At present, he is working as Associate professor of organic chemistry at King Khalid University, Abha, Saudi Arabia

nasirrasool@gcuf.edu.pk

Received Date: 1 October 2023
Revised Date: 22 December 2023
Accepted Date: 2 January 2024
Available Online: 6 January 2024

Figures(55)

In the quest for new agrochemicals and pharmaceuticals, chemists seek access to reliable and mild synthetic techniques to allow for the systematic modification of chemical structures, exploration of unexplored chemical space, and facilitation of practical synthesis in their search for novel agrochemicals and pharmaceuticals. In this regard, photocatalytic reactions enabled the synthesis of intricate and more functionalized compounds. This review overviews the developed synthetic methodologies and their utility in the chemical synthesis of pharmaceuticals. This review also offers in-depth insights into contemporary photoredox reactions such as allylic additions, cyclization, reductive cross-coupling, CH activation, ring opening, oxidative cross-coupling, dehydrogenation, desulphonation, and decarboxylation. It provides a positive outlook for the promising future of this field.
- Photocatalyst,
- Photochemical reactions,
- Drugs,
- Natural products,
- Late-stage functionalization
1. [1]
  C.K. Prier, D.A. Rankic, D.W. MacMillan, Chem. Rev. 113 (2013) 5322–5363. doi: 10.1021/cr300503r
2. [2]
  K. Kalyanasundaram, Coord. Chem. Rev. 46 (1982) 159–244. doi: 10.1016/0010-8545(82)85003-0
3. [3]
  A. Juris, V. Balzani, F. Barigelletti, et al., Coordin. Chem. Rev. 84 (1988) 85–277. doi: 10.1016/0010-8545(88)80032-8
4. [4]
  K.L. Wang, H.T. Ji, L.J. Ou, W.M. He, Eur. J. Org. Chem. 26 (2023) e202300752.
5. [5]
  G. Ciamician, P. Silber, Chem. Lichtwirkungen, Ber. Dtsch. Chem. Ges. 41 (1908) 1071–1080. doi: 10.1002/cber.190804101211
6. [6]
  A. Albini, M. Fagnoni, Green Chem. 6 (2004) 1–6. doi: 10.1039/b309592d
7. [7]
  M.H. Shaw, J. Twilton, D.W. MacMillan, J. Org. Chem. 81 (2016) 6898–6926. doi: 10.1021/acs.joc.6b01449
8. [8]
  V. Srivastava, P.K. Singh, S. Tivari, P.P. Singh, Org. Chem. Front. 9 (2022) 1485–1507. doi: 10.1039/D1QO01602D
9. [9]
  B. Dam, A.K. Sahoo, B.K. Patel, Green Chem. 24 (2022) 7122–7130. doi: 10.1039/D2GC02254K
10. [10]
  Y. Zhou, Y. Qin, Q. Wang, Z. Zhang, G. Zhu, Angew. Chem. 134 (2022) e202110864. doi: 10.1002/ange.202110864
11. [11]
  P.P. Singh, P.K. Singh, V. Srivastava, Org. Chem. Front. 10 (2023) 216–236. doi: 10.1039/D2QO01582J
12. [12]
  M.P. Wiesenfeldt, J.A. Rossi-Ashton, I.B. Perry, et al., Nature 618 (2023) 513–518. doi: 10.1038/s41586-023-06021-8
13. [13]
  D. Yang, Q. Yan, E. Zhu, J. Lv, W.M. He, Chin. Chem. Lett. 33 (2022) 1798–1816. doi: 10.1016/j.cclet.2021.09.068
14. [14]
  L. Wang, P. Bao, W. Liu, et al., Chin. J. Org. Chem. 38 (2018) 3189. doi: 10.6023/cjoc201807014
15. [15]
  L. Zheng, X. Zhuo, Y. Wang, et al., Org. Chem. Front. 9 (2022) 3012–3021. doi: 10.1039/D2QO00253A
16. [16]
  W.B. He, L.Q. Gao, X.J. Chen, Chin. Chem. Lett. 31 (2020) 1895–1898. doi: 10.1016/j.cclet.2020.02.011
17. [17]
  Z. Guo, X. Liu, R. Bai, et al., Inorg. Chem. 60 (2021) 8672–8681. doi: 10.1021/acs.inorgchem.1c00642
18. [18]
  K. Sun, G. Li, Y. Li, et al., Adv. Synth. Catal. 362 (2020) 1947–1954. doi: 10.1002/adsc.202000040
19. [19]
  M.T. Pirnot, D.A. Rankic, D.B. Martin, D.W. MacMillan, Science 339 (2013) 1593–1596. doi: 10.1126/science.1232993
20. [20]
  M. González-Esguevillas, J. Miró, J.L. Jeffrey, D.W. MacMillan, Tetrahedron 141 (2023) 133494. doi: 10.1016/j.tet.2023.133494
21. [21]
  J.H. Shen, M. Shi, Y. Wei, Chem. Eur. J. 29 (2023) e202301157. doi: 10.1002/chem.202301157
22. [22]
  P. Chuentragool, D. Yadagiri, T. Morita, et al., Angew. Chem. 131 (2019) 1808–1812. doi: 10.1002/ange.201812398
23. [23]
  N. Kvasovs, V. Gevorgyan, Chem. Soc. Rev. 50 (2021) 2244–2259. doi: 10.1039/D0CS00589D
24. [24]
  M. Rivas, V. Palchykov, X. Jia, V. Gevorgyan, Nat. Rev. Chem. 6 (2022) 544–561. doi: 10.1038/s41570-022-00403-8
25. [25]
  D.A. Nicewicz, D.W. MacMillan, Science 322 (2008) 77–80. doi: 10.1126/science.1161976
26. [26]
  L. Shi, W. Xia, Chem. Soc. Rev. 41 (2012) 7687–7697. doi: 10.1039/c2cs35203f
27. [27]
  J.M. Narayanam, C.R. Stephenson, Chem. Soc. Rev. 40 (2011) 102–113. doi: 10.1039/B913880N
28. [28]
  T.P. Yoon, M.A. Ischay, J. Du, Nat. Chem. 2 (2010) 527–532. doi: 10.1038/nchem.687
29. [29]
  D.M. Schultz, T.P. Yoon, Science 343 (2014) 1239176. doi: 10.1126/science.1239176
30. [30]
  M.W. Johnson, K.I. Hannoun, Y. Tan, G.C. Fu, J.C. Peters, Chem. Sci. 7 (2016) 4091–4100. doi: 10.1039/C5SC04709A
31. [31]
  P. Marquetand, Chem. Rev. 122 (2022) 15996–15997. doi: 10.1021/acs.chemrev.2c00703
32. [32]
  Y.M. Tian, X.N. Guo, H. Braunschweig, U. Radius, T.B. Marder, Chem. Rev. 121 (2021) 3561–3597. doi: 10.1021/acs.chemrev.0c01236
33. [33]
  M. Fagnoni, D. Dondi, D. Ravelli, Chem. Rev. 107 (2007) 2725–2756. doi: 10.1021/cr068352x
34. [34]
  M.J. Genzink, J.B. Kidd, W.B. Swords, T.P. Yoon, Chem. Rev. 122 (2021) 1654–1716.
35. [35]
  K.L. Skubi, T.R. Blum, T.P. Yoon, Chem. Rev. 116 (2016) 10035–10074. doi: 10.1021/acs.chemrev.6b00018
36. [36]
  T. Nevesely, M. Wienhold, J.J. Molloy, R. Gilmour, Chem. Rev. 122 (2021) 2650–2694.
37. [37]
  D.C. Blakemore, L. Castro, I. Churcher, et al., Nat. Chem. 10 (2018) 383–394. doi: 10.1038/s41557-018-0021-z
38. [38]
  K.R. Campos, P.J. Coleman, J.C. Alvarez, et al., Science 363 (2019) eaat0805. doi: 10.1126/science.aat0805
39. [39]
  K.D.C. Lisa Candish, G.C. Cook, J.J. Douglas, et al., Chem. Rev. 122 (2022) 2907–2980. doi: 10.1021/acs.chemrev.1c00416
40. [40]
  T. Cernak, K.D. Dykstra, S. Tyagarajan, P. Vachal, S.W. Krska, Chem. Soc. Rev. 45 (2016) 546–576. doi: 10.1039/C5CS00628G
41. [41]
  M. Moir, J.J. Danon, T.A. Reekie, M. Kassiou, Expert Opin. Drug Discov. 14 (2019) 1137–1149. doi: 10.1080/17460441.2019.1653850
42. [42]
  L. Capaldo, L.L. Quadri, D. Ravelli, Green Chem. 22 (2020) 3376–3396. doi: 10.1039/D0GC01035A
43. [43]
  R. Cannalire, S. Pelliccia, L. Sancineto, et al., Chem. Soc. Rev. 50 (2021) 766–897. doi: 10.1039/D0CS00493F
44. [44]
  P. Bellotti, H.M. Huang, T. Faber, F. Glorius, Chem. Rev. 123 (2023) 4237–4352. doi: 10.1021/acs.chemrev.2c00478
45. [45]
  A. Trowbridge, D. Reich, M.J. Gaunt, Nature 561 (2018) 522–527. doi: 10.1038/s41586-018-0537-9
46. [46]
  M.D. Eastgate, M.A. Schmidt, K.R. Fandrick, Nat. Rev. Chem. 1 (2017) 0016. doi: 10.1038/s41570-017-0016
47. [47]
  R.W. Hoffmann, Chem. Soc. Rev. 45 (2016) 577–583. doi: 10.1039/C5CS00423C
48. [48]
  A.G. Csákÿ, G. de la Herrán, M.C. Murcia, Chem. Soc. Rev. 39 (2010) 4080–4102. doi: 10.1039/b924486g
49. [49]
  J. Zhao, J.L. Brosmer, Q. Tang, et al., J. Am. Chem. Soc. 139 (2017) 9807–9810. doi: 10.1021/jacs.7b05277
50. [50]
  M. Ikeda, K. Ohno, S.I. Mohri, M. Takahashi, Y. Tamura, J. Chem. Soc., Perkin Trans. 1 (1984) 405–412.
51. [51]
  M. Teders, C. Henkel, L. Anhäuser, et al., Nat. Chem. 10 (2018) 981–988. doi: 10.1038/s41557-018-0102-z
52. [52]
  C. Palomo, M. Oiarbide, J.M. García, Chem. Soc. Rev. 33 (2004) 65–75. doi: 10.1039/B202901D
53. [53]
  J. Xu, C. Boyer, Macromolecules 48 (2015) 520–529. doi: 10.1021/ma502460t
54. [54]
  T. Rossolini, J.A. Leitch, R. Grainger, D.J. Dixon, Org. Lett. 20 (2018) 6794–6798. doi: 10.1021/acs.orglett.8b02923
55. [55]
  J.S. Wang, K. Wu, C. Yin, et al., Nat. Commun. 11 (2020) 4675. doi: 10.1038/s41467-020-18487-5
56. [56]
  S. Vijayakrishnan, J.W. Ward, A.I. Cooper, ACS Catal. 12 (2022) 10057–10064. doi: 10.1021/acscatal.2c02743
57. [57]
  F. Denes, M. Pichowicz, G. Povie, P. Renaud, Chem. Rev. 114 (2014) 2587–2693. doi: 10.1021/cr400441m
58. [58]
  G. Ciamician, Science 36 (1912) 385–394. doi: 10.1126/science.36.926.385
59. [59]
  J. Metternich, R. Gilmour, Synlett 27 (2016) 2541–2552. doi: 10.1055/s-0036-1588621
60. [60]
  Z. Lu, T.P. Yoon, Angew. Chem. 124 (2012) 10475–10478. doi: 10.1002/ange.201204835
61. [61]
  T.R. Blum, Z.D. Miller, D.M. Bates, I.A. Guzei, T.P. Yoon, Science 354 (2016) 1391–1395. doi: 10.1126/science.aai8228
62. [62]
  E.R. Welin, C. Le, D.M. Arias-Rotondo, J.K. McCusker, D.W. MacMillan, Science 355 (2017) 380–385. doi: 10.1126/science.aal2490
63. [63]
  J. Mayol-Llinas, A. Nelson, W. Farnaby, A. Ayscough, Drug Discov. Today 22 (2017) 965–969. doi: 10.1016/j.drudis.2017.01.008
64. [64]
  V. Lahmy, R. Long, D. Morin, V. Villard, T. Maurice, Front. Cell. Neurosci. 8 (2015) 463.
65. [65]
  D.P. Marciano, M.R. Chang, C.A. Corzo, et al., Cell Metab. 19 (2014) 193–208. doi: 10.1016/j.cmet.2013.12.009
66. [66]
  P. Ruiz-Castillo, S.L. Buchwald, Chem. Rev. 116 (2016) 12564–12649. doi: 10.1021/acs.chemrev.6b00512
67. [67]
  S.B. Herzon, J.F. Hartwig, J. Am. Chem. Soc. 130 (2008) 14940–14941. doi: 10.1021/ja806367e
68. [68]
  L. Huang, M. Arndt, K. t. Gooßen, H. Heydt, L.J. Goossen, Chem. Rev. 115 (2015) 2596–2697. doi: 10.1021/cr300389u
69. [69]
  P. Kalck, M. Urrutigoity, Chem. Rev. 118 (2018) 3833–3861. doi: 10.1021/acs.chemrev.7b00667
70. [70]
  F. Perez, S. Oda, L.M. Geary, M.J. Krische, Top. Curr. Chem. 374 (2016) 365–387.
71. [71]
  M. Chilamari, J.R. Immel, S. Bloom, ACS Catal. 10 (2020) 12727–12737. doi: 10.1021/acscatal.0c03422
72. [72]
  G. Wuitschik, E.M. Carreira, B. r. Wagner, et al., J. Med. Chem. 53 (2010) 3227–3246. doi: 10.1021/jm9018788
73. [73]
  D. Ravelli, M. Zoccolillo, M. Mella, M. Fagnoni, Adv. Synth. Catal. 356 (2014) 2781–2786. doi: 10.1002/adsc.201400027
74. [74]
  S.H. Oh, Y.R. Malpani, N. Ha, Y.S. Jung, S.B. Han, Org. Lett. 16 (2014) 1310–1313. doi: 10.1021/ol403716t
75. [75]
  J. Yang, Z. Sun, K. Yan, et al., Green Chem. 23 (2021) 2756–2762. doi: 10.1039/D1GC00379H
76. [76]
  Y.H. Lu, C. Wu, J.C. Hou, et al., ACS Catal. 13 (2023) 13071–13076. doi: 10.1021/acscatal.3c02268
77. [77]
  H.T. Ji, K.L. Wang, W.T. Ouyang, et al., Green Chem. 25 (2023) 7983–7987. doi: 10.1039/D3GC02575F
78. [78]
  P.V. Fish, A.D. Brown, E. Evrard, L.R. Roberts, Bioorg. Med. Chem. Lett. 19 (2009) 1871–1875. doi: 10.1016/j.bmcl.2009.02.071
79. [79]
  A. Brown, T.B. Brown, A. Calabrese, et al., Bioorg. Med. Chem. Lett. 20 (2010) 516–520. doi: 10.1016/j.bmcl.2009.11.097
80. [80]
  M. Maetani, J. Zoller, B. Melillo, et al., J. Am. Chem. Soc. 139 (2017) 11300–11306. doi: 10.1021/jacs.7b06994
81. [81]
  M.R. Becker, E.R. Wearing, C.S. Schindler, Nat. Chem. 12 (2020) 898–905. doi: 10.1038/s41557-020-0541-1
82. [82]
  F. Wang, C. Chen, G. Deng, C. Xi, J. Org. Chem. 77 (2012) 4148–4151. doi: 10.1021/jo300250x
83. [83]
  F. Ke, Y. Qu, Z. Jiang, et al., Org. Lett. 13 (2011) 454–457. doi: 10.1021/ol102784c
84. [84]
  Z. Chen, Q. Yan, Z. Liu, Y. Zhang, Chem. Eur. J. 20 (2014) 17635–17639. doi: 10.1002/chem.201405057
85. [85]
  M.E. Daub, M. Ehrenshaft, Annu. Rev. Phytopathol. 38 (2000) 461–490. doi: 10.1146/annurev.phyto.38.1.461
86. [86]
  Y. Zhang, Y. Cao, L. Lu, et al., J. Org. Chem. 84 (2019) 7711–7721. doi: 10.1021/acs.joc.9b00545
87. [87]
  J.B. Metternich, R. Gilmour, J. Org. Chem. 138 (2016) 1040–1045.
88. [88]
  G.K. Jana, S. Paul, S. Sinha, Org. Prep. Proc. Int. 43 (2011) 541–573. doi: 10.1080/00304948.2011.629563
89. [89]
  X.Y. Liu, Y. Qin, Acc. Chem. Res. 52 (2019) 1877–1891. doi: 10.1021/acs.accounts.9b00246
90. [90]
  Z. Zhang, D. Yi, M. Zhang, et al., ACS Catal. 10 (2020) 10149–10156. doi: 10.1021/acscatal.0c01841
91. [91]
  M.S. Oderinde, J. Kempson, D. Smith, et al., Eur. J. Org. Chem. 2020 (2020) 41–46. doi: 10.1002/ejoc.201901482
92. [92]
  Y. Bansal, O.J.B. Silakari, Bioorg. Med. Chem. 20 (2012) 6208–6236. doi: 10.1016/j.bmc.2012.09.013
93. [93]
  P.A. Renhowe, S. Pecchi, C.M. Shafer, et al., J. Med. Chem. 52 (2009) 278–292. doi: 10.1021/jm800790t
94. [94]
  C. Zhang, B. Zhong, S. Yang, et al., Bioorg. Med. Chem. 23 (2015) 3774–3780. doi: 10.1016/j.bmc.2015.03.085
95. [95]
  P.D. Verdouw, J.M. Hartog, D.J. Duncker, W. Roth, P.R. Saxena, Eur. J. Pharmacol. 126 (1986) 21–30. doi: 10.1016/0014-2999(86)90733-8
96. [96]
  R. Mocharla, H. Mocharla, M.E. Hodes, Nucleic Acids Res. 15 (1987) 10589. doi: 10.1093/nar/15.24.10589
97. [97]
  Y. Kim, M.R. Kumar, N. Park, Y. Heo, S. Lee, J. Org. Chem. 76 (2011) 9577–9583. doi: 10.1021/jo2019416
98. [98]
  K. Bahrami, M.M. Khodaei, F. Naali, J. Org. Chem. 73 (2008) 6835–6837. doi: 10.1021/jo8010232
99. [99]
  J. Kovvuri, B. Nagaraju, A. Kamal, A.K. Srivastava, ACS Comb. Sci. 18 (2016) 644–650. doi: 10.1021/acscombsci.6b00107
100. [100]
  J.W. Tucker, J.M. Narayanam, S.W. Krabbe, C.R. Stephenson, Org. Lett. 12 (2010) 368–371. doi: 10.1021/ol902703k
101. [101]
  H. Huang, M. Yu, X. Su, et al., J. Org. Chem. 83 (2018) 2425–2437. doi: 10.1021/acs.joc.7b03017
102. [102]
  P.D. Bass, D.A. Gubler, T.C. Judd, R.M. Williams, Chem. Rev. 113 (2013) 6816–6863. doi: 10.1021/cr3001059
103. [103]
  T. Sasase, H. Morinaga, T. Abe, et al., Diabet. Obes. Metab. 11 (2009) 1084–1087. doi: 10.1111/j.1463-1326.2009.01082.x
104. [104]
  V.M. Dembitsky, J. Nat. Med. 62 (2008) 1–33.
105. [105]
  S. Ren, F. Pan, W. Zhang, G.W. Rao, Curr. Med. Chem. 29 (2022) 4113–4135. doi: 10.2174/0929867329666220105120722
106. [106]
  E. Lee-Ruff, G. Mladenova, Chem. Rev. 103 (2003) 1449–1484. doi: 10.1021/cr010013a
107. [107]
  Y. Xu, M.L. Conner, M.K. Brown, Angew. Chem. Int. Ed. 54 (2015) 11918–11928. doi: 10.1002/anie.201502815
108. [108]
  T. Sravanthi, S. Manju, Eur. J. Pharm. Sci. 91 (2016) 1–10. doi: 10.1016/j.ejps.2016.05.025
109. [109]
  N. Chadha, O. Silakari, Eur. J. Med. Chem. 134 (2017) 159–184. doi: 10.1016/j.ejmech.2017.04.003
110. [110]
  M.S. Oderinde, A. Ramirez, T.M. Dhar, et al., J. Org. Chem. 86 (2020) 1730–1747.
111. [111]
  L.R. Orgren, E.E. Maverick, C.C. Marvin, J. Org. Chem. 80 (2015) 12635–12640. doi: 10.1021/acs.joc.5b02199
112. [112]
  A. Brossi, L. Chopard-dit-Jean, O. Schnider, Helv. Chim. Acta 41 (1958) 1793–1806. doi: 10.1002/hlca.19580410634
113. [113]
  B. Giese, B. Kopping, T. Göbel, et al., Org. React. 48 (2004) 301–856.
114. [114]
  Y. Liu, M. Zhang, C.H. Tung, Y. Wang, ACS Catal. 6 (2016) 8389–8394. doi: 10.1021/acscatal.6b03076
115. [115]
  Z. Li, H. Song, R. Guo, et al., Green Chem. 21 (2019) 3602–3605. doi: 10.1039/C9GC01359H
116. [116]
  X. Zhuang, X. Shi, R. Zhu, et al., Org. Chem. Front. 8 (2021) 736–742. doi: 10.1039/D0QO01188F
117. [117]
  S. Özden, D. Atabey, S. Yıldız, H. Göker, Bioorg. Med. Chem. 13 (2005) 1587–1597. doi: 10.1016/j.bmc.2004.12.025
118. [118]
  J.Y. Chai, B.K. Jung, S.J. Hong, Korean J. Parasitol. 59 (2021) 189. doi: 10.3347/kjp.2021.59.3.189
119. [119]
  S.M. Sondhi, S. Rajvanshi, M. Johar, et al., Eur. J. Med. Chem. 37 (2002) 835–843. doi: 10.1016/S0223-5234(02)01403-4
120. [120]
  X.Z. Guo, L. Shi, R. Wang, et al., Bioorg. Med. Chem. 16 (2008) 10301–10310. doi: 10.1016/j.bmc.2008.10.040
121. [121]
  A. Chimirri, A. De Sarro, G. De Sarro, R. Gitto, M. Zappala, Farmaco 56 (2001) 821–826. doi: 10.1016/S0014-827X(01)01147-8
122. [122]
  A. Lee-Dutra, K.L. Arienti, D.J. Buzard, et al., Bioorg. Med. Chem. Lett. 16 (2006) 6043–6048. doi: 10.1016/j.bmcl.2006.08.117
123. [123]
  M.J. O'Neil, M. Smith, P. Heckelman, The Merck Index, 13th Edition, Merck and Co, Inc NJ, 2001, p. 1785.
124. [124]
  I. Siddiqui, F. Ibad, A. Ibad, M.A. Waseem, G. Watal, Tetrahedron Lett. 57 (2016) 5–10. doi: 10.1016/j.tetlet.2015.10.042
125. [125]
  A. Armstrong, J.C. Collins, Angew. Chem. Int. Ed. 49 (2010) 2282–2285. doi: 10.1002/anie.200906750
126. [126]
  A. Gauld, STEPS: suvorexant (Belsomra) for insomnia, Am. Fam. Phys. 93 (2016) 1016.
127. [127]
  V.S. Patil, D.V. Patil, S.S. Potdar, Org. Commun. 15 (2022) 71–80.
128. [128]
  V.K. Yadav, V.P. Srivastava, L.D.S. Yadav, Tetrahedron Lett. 57 (2016) 155–158. doi: 10.1016/j.tetlet.2015.11.089
129. [129]
  S. Zykova, S. Shurov, V. Talismanov, et al., J. Pharm. Sci. Res. 10 (2018) 947–949.
130. [130]
  Z.P. Ye, Y.Z. Hu, J.P. Guan, et al., Org. Lett. 23 (2021) 4754–4758. doi: 10.1021/acs.orglett.1c01477
131. [131]
  G. Zhou, X. Deng, C. Pan, et al., Chem. Comm. 56 (2020) 12546–12549. doi: 10.1039/D0CC04471G
132. [132]
  C. Russo, R. Cannalire, P. Luciano, et al., Synthesis 53 (2021) 4419–4427. doi: 10.1055/a-1543-3924
133. [133]
  G.E. Crisenza, P. Melchiorre, Nat. Commun. 11 (2020) 1–4. doi: 10.1038/s41467-019-13993-7
134. [134]
  V.R. Solomon, H. Lee, Curr. Med. Chem. 18 (2011) 1488–1508. doi: 10.2174/092986711795328382
135. [135]
  J.X. Xu, N.L. Pan, J.X. Chen, J.W. Zhao, J. Org. Chem. 86 (2021) 10747–10754. doi: 10.1021/acs.joc.1c01386
136. [136]
  J. Ma, F. Schäfers, C. Daniliuc, et al., Angew. Chem. 132 (2020) 9726–9732. doi: 10.1002/ange.202001200
137. [137]
  C.E. Knappke, S. Grupe, D. Gärtner, et al., Chem. Eur. J. 20 (2014) 6828–6842. doi: 10.1002/chem.201402302
138. [138]
  D.A. Everson, D.J. Weix, J. Org. Chem. 79 (2014) 4793–4798. doi: 10.1021/jo500507s
139. [139]
  P.J. Xia, Z.P. Ye, D. Song, et al., Chem. Comm. 55 (2019) 2712–2715. doi: 10.1039/C8CC09385G
140. [140]
  X. Tian, Y. Guo, W. An, et al., Nat. Commun. 13 (2022) 6186. doi: 10.1038/s41467-022-33778-9
141. [141]
  S. Tripathi, L.D.S. Yadav, New J. Chem. 42 (2018) 3765–3769. doi: 10.1039/C7NJ04578F
142. [142]
  R.W. Gantt, P. Peltier-Pain, J.S. Thorson, Nat. Prod. Rep. 28 (2011) 1811–1853. doi: 10.1039/c1np00045d
143. [143]
  Y. Yang, B. Yu, Chem. Rev. 117 (2017) 12281–12356. doi: 10.1021/acs.chemrev.7b00234
144. [144]
  Q. Wu, J.G. Cho, D.S. Lee, et al., Carbohydr. Res. 372 (2013) 9–14. doi: 10.1016/j.carres.2012.09.015
145. [145]
  W. Disadee, C. Mahidol, P. Sahakitpichan, et al., Phytochemistry 74 (2012) 115–122. doi: 10.1016/j.phytochem.2011.11.001
146. [146]
  T. Kawamata, M. Nagatomo, M. Inoue, J. Am. Chem. Soc. 139 (2017) 1814–1817. doi: 10.1021/jacs.6b13263
147. [147]
  S.O. Badir, A. Dumoulin, J.K. Matsui, G.A. Molander, Angew. Chem. Int. Ed. 57 (2018) 6610–6613. doi: 10.1002/anie.201800701
148. [148]
  X. Wang, J. Dong, Y. Liu, H. Song, Q. Wang, Chin. Chem. Lett. 32 (2021) 3027–3030. doi: 10.1016/j.cclet.2021.03.070
149. [149]
  M.P. DeMartino, K. Chen, P.S. Baran, J. Am. Chem. Soc. 130 (2008) 11546–11560. doi: 10.1021/ja804159y
150. [150]
  Y. Kuang, K. Wang, X. Shi, et al., Angew. Chem. 131 (2019) 17015–17019. doi: 10.1002/ange.201910414
151. [151]
  S. Li, P.W. Davies, W. Shu, Chem. Sci. 13 (2022) 6636–6641. doi: 10.1039/D2SC01905A
152. [152]
  N.A. Romero, K.A. Margrey, N.E. Tay, D.A. Nicewicz, Science 349 (2015) 1326–1330. doi: 10.1126/science.aac9895
153. [153]
  J.K. Matsui, D.N. Primer, G.A. Molander, Chem. Sci. 8 (2017) 3512–3522. doi: 10.1039/C7SC00283A
154. [154]
  H. Liu, L. Ge, D.X. Wang, N. Chen, C. Feng, Angew. Chem. 131 (2019) 3958–3962. doi: 10.1002/ange.201814308
155. [155]
  M.A. Miranda, M.L. Marin, Curr. Opin. Green Sustain. Chem. 6 (2017) 139–149. doi: 10.1016/j.cogsc.2017.05.001
156. [156]
  L. Guillemard, N. Kaplaneris, L. Ackermann, M.J. Johansson, Nat. Rev. Chem. 5 (2021) 522–545. doi: 10.1038/s41570-021-00300-6
157. [157]
  B. Liu, L. Yang, P. Li, F. Wang, X. Li, Org. Chem. Front. 8 (2021) 1085–1101. doi: 10.1039/D0QO01159B
158. [158]
  K.J. Jiao, Y.K. Xing, Q.L. Yang, H. Qiu, T.S. Mei, Acc. Chem. Res. 53 (2020) 300–310. doi: 10.1021/acs.accounts.9b00603
159. [159]
  S. Vidyacharan, B.T. Ramanjaneyulu, S. Jang, D.P. Kim, ChemSusChem 12 (2019) 2581–2586. doi: 10.1002/cssc.201900736
160. [160]
  C. Hou, S. Sun, Z. Liu, et al., Adv. Synth. Catal. 363 (2021) 2806–2812. doi: 10.1002/adsc.202100168
161. [161]
  H.Y. Song, F. Xiao, J. Jiang, et al., Chin. Chem. Lett. (2023) 108509.
162. [162]
  H. Xu, X. Li, J. Ma, et al., Chin. Chem. Lett. (2023) 108403.
163. [163]
  H. Cerecetto, A. Gerpe, M. Gonzalez, V.J. Aran, C.O. de Ocariz, Mini-Rev. Med. Chem. 5 (2005) 869–878. doi: 10.2174/138955705774329564
164. [164]
  X. Li, S. Chu, V.A. Feher, et al., J. Med. Chem. 46 (2003) 5663–5673. doi: 10.1021/jm0302039
165. [165]
  G. Picciola, F. Ravenna, G. Carenini, P. Gentili, M. Riva, Il Farmaco, Edizione Sci. 36 (1981) 1037–1056.
166. [166]
  W. Han, J.C. Pelletier, C.N. Hodge, Bioorg. Med. Chem. Lett. 8 (1998) 3615–3620. doi: 10.1016/S0960-894X(98)00659-3
167. [167]
  J. Liu, C. Qian, Y. Zhu, et al., Bioorg. Med. Chem. 26 (2018) 747–757. doi: 10.1016/j.bmc.2017.12.041
168. [168]
  S.V. Keisner, S.R. Shah, Drugs 71 (2011) 443–454.
169. [169]
  A. Unsinn, P. Knochel, Chem. Comm. 48 (2012) 2680–2682. doi: 10.1039/c2cc17804d
170. [170]
  S.A. Ohnmacht, A.J. Culshaw, M.F. Greaney, Org. Lett. 12 (2010) 224–226. doi: 10.1021/ol902537d
171. [171]
  X. Ding, J. Bai, H. Wang, et al., Tetrahedron 73 (2017) 172–178. doi: 10.1016/j.tet.2016.11.066
172. [172]
  G. Bogonda, H.Y. Kim, K. Oh, Org. Lett. 20 (2018) 2711–2715. doi: 10.1021/acs.orglett.8b00920
173. [173]
  W. Zhang, X.X. Xiang, J. Chen, et al., Nat. Commun. 11 (2020) 1–10. doi: 10.1038/s41467-019-13993-7
174. [174]
  P. Nuhant, M.S. Oderinde, J. Genovino, et al., Angew. Chem. Int. Ed. 56 (2017) 15309–15313. doi: 10.1002/anie.201707958
175. [175]
  Q.Q. Han, D.M. Chen, Z.L. Wang, et al., Chin. Chem. Lett. 32 (2021) 2559–2561. doi: 10.1016/j.cclet.2021.02.018
176. [176]
  M.D. Tzirakis, I.N. Lykakis, M. Orfanopoulos, Chem. Soc. Rev. 38 (2009) 2609–2621. doi: 10.1039/b812100c
177. [177]
  D. Mazzarella, A. Pulcinella, L. Bovy, R. Broersma, T. Noël, Angew. Chem. Int. Ed. 60 (2021) 21277–21282. doi: 10.1002/anie.202108987
178. [178]
  Y.W. Zheng, R. Narobe, K. Donabauer, S. Yakubov, B. König, ACS Catal. 10 (2020) 8582–8589. doi: 10.1021/acscatal.0c01924
179. [179]
  J.Y. Dong, H.P. He, Y.M. Shen, K.Q. Zhang, J. Nat. Prod. 68 (2005) 1510–1513. doi: 10.1021/np0502241
180. [180]
  C. Takahashi, A. Numata, E. Matsumura, et al., J. Antibiot. 47 (1994) 1242–1249. doi: 10.7164/antibiotics.47.1242
181. [181]
  C.J. Zheng, C.J. Kim, K.S. Bae, Y.H. Kim, W.G. Kim, J. Nat. Prod. 69 (2006) 1816–1819. doi: 10.1021/np060348t
182. [182]
  L. Furst, J.M. Narayanam, C.R. Stephenson, Angew. Chem. Int. Ed. 50 (2011) 9655. doi: 10.1002/anie.201103145
183. [183]
  D.A. Nagib, D.W. MacMillan, Nature 480 (2011) 224–228. doi: 10.1038/nature10647
184. [184]
  I.B. Seiple, S. Su, R.A. Rodriguez, et al., J. Am. Chem. Soc. 132 (2010) 13194–13196. doi: 10.1021/ja1066459
185. [185]
  R. Pschorr, Ber. Dtsch. Chem. Ges. 29 (1896) 496–501. doi: 10.1002/cber.18960290198
186. [186]
  D. Xue, Z.H. Jia, C.J. Zhao, et al., Chem. Eur. J. 20 (2014) 2960–2965. doi: 10.1002/chem.201304120
187. [187]
  E.R. Welin, A.A. Warkentin, J.C. Conrad, D.W. MacMillan, Angew. Chem. Int. Ed. 54 (2015) 9668–9672. doi: 10.1002/anie.201503789
188. [188]
  A. Singh, A. Arora, J.D. Weaver, Org. Lett. 15 (2013) 5390–5393. doi: 10.1021/ol402751j
189. [189]
  D.A. DiRocco, K. Dykstra, S. Krska, et al., Angew. Chem. Int. Ed. 53 (2014) 4802–4806. doi: 10.1002/anie.201402023
190. [190]
  G. Lei, M. Xu, R. Chang, I. Funes-Ardoiz, J. Ye, J. Am. Chem. Soc. 143 (2021) 11251–11261. doi: 10.1021/jacs.1c05852
191. [191]
  J.M. Mayer, Acc. Chem. Res. 44 (2011) 36–46. doi: 10.1021/ar100093z
192. [192]
  M. Costas, M. Bietti, Acc. Chem. Res. 51 (2018) 2601–2602. doi: 10.1021/acs.accounts.8b00525
193. [193]
  C.R. Stephenson, T.P. Yoon, D.W. MacMillan, Visible Light Photocatalysis In Organic Chemistry, John Wiley & Sons, 2018.
194. [194]
  D. Staveness, I. Bosque, C.R. Stephenson, Acc. Chem. Res. 49 (2016) 2295–2306. doi: 10.1021/acs.accounts.6b00270
195. [195]
  B.P. Roberts, Chem. Soc. Rev. 28 (1999) 25–35. doi: 10.1039/a804291h
196. [196]
  S. Cao, W. Hong, Z. Ye, L. Gong, Nat. Commun. 12 (2021) 2377. doi: 10.1038/s41467-021-22690-3
197. [197]
  H. Du, C. Fairbridge, H. Yang, Z. Ring, Appl. Catal. A: Gen. 294 (2005) 1–21. doi: 10.1016/j.apcata.2005.06.033
198. [198]
  W. Zhang, Y.L. Pan, C. Yang, X. Li, B. Wang, Org. Chem. Front. 6 (2019) 2765–2770. doi: 10.1039/C9QO00625G
199. [199]
  X. Zhu, X. Song, X. Li, et al., Adv. Synth. Catal. 364 (2022) 4384–4391. doi: 10.1002/adsc.202201143
200. [200]
  W. Ou, G. Zhang, J. Wu, C. Su, ACS Catal. 9 (2019) 5178–5183. doi: 10.1021/acscatal.9b00693
201. [201]
  X.Z. Fan, J.W. Rong, H.L. Wu, et al., Angew. Chem. 130 (2018) 8650–8654. doi: 10.1002/ange.201803220
202. [202]
  I. Funes-Ardoiz, F. Maseras, ACS Catal. 8 (2018) 1161–1172. doi: 10.1021/acscatal.7b02974
203. [203]
  H.Y. Song, J. Jiang, C. Wu, et al., Green Chem. 25 (2023) 3292–3296. doi: 10.1039/D2GC04843D
204. [204]
  J. Li, J. Chen, R. Sang, et al., Nat. Chem. 12 (2020) 56–62. doi: 10.1038/s41557-019-0353-3
205. [205]
  X. Sun, J. Chen, T. Ritter, Nat. Chem. 10 (2018) 1229–1233. doi: 10.1038/s41557-018-0142-4
206. [206]
  H.G. Yayla, F. Peng, I.K. Mangion, et al., Chem. Sci. 7 (2016) 2066–2073. doi: 10.1039/C5SC03350K
207. [207]
  J.J. Douglas, H. Albright, M.J. Sevrin, K.P. Cole, C.R. Stephenson, Angew. Chem. Int. Ed. 54 (2015) 14898–14902. doi: 10.1002/anie.201507369
208. [208]
  Y.F. Liang, M. Bilal, L.Y. Tang, et al., Chem. Rev. 123 (2023) 12313–12370. doi: 10.1021/acs.chemrev.3c00219
209. [209]
  C.C. Le, D.W. MacMillan, J. Am. Chem. Soc. 137 (2015) 11938–11941. doi: 10.1021/jacs.5b08304
210. [210]
  V.K. Soni, S. Lee, J. Kang, et al., ACS Catal. 9 (2019) 10454–10463. doi: 10.1021/acscatal.9b03435
211. [211]
  C. Ma, Z. Feng, J. Li, et al., Org. Chem. Front. 8 (2021) 3286–3291. doi: 10.1039/D1QO00064K
212. [212]
  X. Shu, R. Xu, S. Liao, Sci. China Chem. 64 (2021) 1756–1762. doi: 10.1007/s11426-021-1048-4
213. [213]
  R. Xu, T. Xu, M. Yang, T. Cao, S. Liao, Nat. Commun. 10 (2019) 3752. doi: 10.1038/s41467-019-11805-6
214. [214]
  K. Okada, K. Okamoto, M. Oda, J. Am. Chem. Soc. 110 (1988) 8736–8738. doi: 10.1021/ja00234a047
215. [215]
  D.M. Gale, W.J. Middleton, C.G. Krespan, J. Am. Chem. Soc. 88 (1966) 3617–3623. doi: 10.1021/ja00967a026
216. [216]
  D.H. Barton, J.C. Jaszberenyi, E.A. Theodorakis, J. Reibenspies, J. Am. Chem. Soc. 115 (1993) 8050–8059. doi: 10.1021/ja00071a017
1. [1]
  Xiaoming Fu , Haibo Huang , Guogang Tang , Jingmin Zhang , Junyue Sheng , Hua Tang . Recent advances in g-C3N4-based direct Z-scheme photocatalysts for environmental and energy applications. Chinese Journal of Structural Chemistry, 2024, 43(2): 100214-100214. doi: 10.1016/j.cjsc.2024.100214
2. [2]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
3. [3]
  Peng Chen , Lijuan Liang , Yufei Zhu , Zhimin Xing , Zhenhua Jia , Teck-Peng Loh . Strategies for constructing seven-membered rings: Applications in natural product synthesis. Chinese Chemical Letters, 2024, 35(6): 109229-. doi: 10.1016/j.cclet.2023.109229
4. [4]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
5. [5]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
6. [6]
  Yuan Zhang , Shenghao Gong , A.R. Mahammed Shaheer , Rong Cao , Tianfu Liu . Plasmon-enhanced photocatalytic oxidative coupling of amines in the air using a delicate Ag nanowire@NH₂-UiO-66 core-shell nanostructures. Chinese Chemical Letters, 2024, 35(4): 108587-. doi: 10.1016/j.cclet.2023.108587
7. [7]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
8. [8]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
9. [9]
  Deli Chen , Jiawen Li , Xudong Xu , Zhaocui Sun , Yun Yang , Minghui Xu , Hanqiao Liang , Junshan Yang , Hui Meng , Guoxu Ma , Jianhe Wei . Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus. Chinese Chemical Letters, 2024, 35(10): 109451-. doi: 10.1016/j.cclet.2023.109451
10. [10]
  Chenye An , Abiduweili Sikandaier , Xue Guo , Yukun Zhu , Hua Tang , Dongjiang Yang . 红磷纳米颗粒嵌入花状CeO₂分级S型异质结高效光催化产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2405019-. doi: 10.3866/PKU.WHXB202405019
11. [11]
  Kun Tang , Yu-Wu Zhong . Water reduction by an organic single-chromophore photocatalyst. Chinese Journal of Structural Chemistry, 2024, 43(8): 100376-100376. doi: 10.1016/j.cjsc.2024.100376
12. [12]
  Haojie Song , Laiyu Luo , Siyu Wang , Guo Zhang , Baojiang Jiang . Advances in poly(heptazine imide)/poly(triazine imide) photocatalyst. Chinese Chemical Letters, 2024, 35(10): 109347-. doi: 10.1016/j.cclet.2023.109347
13. [13]
  Bicheng Zhu , Jingsan Xu . S-scheme heterojunction photocatalyst for H2 evolution coupled with organic oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100327-100327. doi: 10.1016/j.cjsc.2024.100327
14. [14]
  Zongyi Huang , Cheng Guo , Quanxing Zheng , Hongliang Lu , Pengfei Ma , Zhengzhong Fang , Pengfei Sun , Xiaodong Yi , Zhou Chen . Efficient photocatalytic biomass-alcohol conversion with simultaneous hydrogen evolution over ultrathin 2D NiS/Ni-CdS photocatalyst. Chinese Chemical Letters, 2024, 35(7): 109580-. doi: 10.1016/j.cclet.2024.109580
15. [15]
  Yuhao Ma , Yufei Zhou , Mingchuan Yu , Cheng Fang , Shaoxia Yang , Junfeng Niu . Covalently bonded ternary photocatalyst comprising MoSe₂/black phosphorus nanosheet/graphitic carbon nitride for efficient moxifloxacin degradation. Chinese Chemical Letters, 2024, 35(9): 109453-. doi: 10.1016/j.cclet.2023.109453
16. [16]
  Zhiwei Zhong , Yanbin Huang , Wantai Yang . A simple photochemical method for surface fluorination using perfluoroketones. Chinese Chemical Letters, 2024, 35(5): 109339-. doi: 10.1016/j.cclet.2023.109339
17. [17]
  Xiaoliu Liang , Chunliu Huang , Hui Liu , Hu Chen , Jiabao Shou , Hongwei Cheng , Gang Liu . Natural hydrogel dressings in wound care: Design, advances, and perspectives. Chinese Chemical Letters, 2024, 35(10): 109442-. doi: 10.1016/j.cclet.2023.109442
18. [18]
  Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
19. [19]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
20. [20]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(151)
HTML views(5)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142