Citation: Yang Fanzhi, Zhang Han, Liu Xuri, Wang Bo, Ackermann Lutz. Transition Metal-Catalyzed Regio-selective Aromatic C—H Bond Oxidation for C—O Bond Formation[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 59-73. doi: 10.6023/cjoc201808017 shu

Transition Metal-Catalyzed Regio-selective Aromatic C—H Bond Oxidation for C—O Bond Formation

  • Corresponding author: Yang Fanzhi, yangfanzhi@bit.edu.cn Wang Bo, bowang@bit.edu.cn Ackermann Lutz, Lutz.Ackermann@chemie.uni-goettingen.de
  • Received Date: 16 August 2018
    Revised Date: 22 October 2018
    Available Online: 26 January 2018

    Fund Project: the National Natural Science Foundation of China 21801018the Beijing Institute of Technology Research Fund Program for Young Scholars 1230011181807Project supported by the National Natural Science Foundation of China (No. 21801018) and the Beijing Institute of Technology Research Fund Program for Young Scholars (No. 1230011181807)

Figures(31)

  • Recent years the great progress in transition metal-catalyzed direct aromatic C—H oxidation has been witnessed, which has been utilized in the preparation of various phenolic compounds. These transformations employ inter alia palladium, copper, ruthenium, iridium, etc. as the transition metal catalysts, and hypervalent iodine, persulfate, or oxygen as the oxidants. There have been several reviews in which the C—H oxidations with specific transition metal or oxidant was discussed. This review focuses specifically on transition metal-catalyzed aromatic C—H oxidations with ortho-, meta-, or para-selectivity, and rationalizes the possible generation mechanism of regio-selectivities, which might be controlled by the directing group via chelation-assistance, the ligand, or intrinsic properties of the substrate. The discussion section indicated the existing problems of transition metal-catalyzed aromatic C—H oxidations, as well as the possible limiting factors for the development and application of this strategy.
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    1. [1]

      (a) Rappoport, Z. The Chemistry of Phenols, Wiley-VCH, Weinheim, 2003.
      (b) Fiegel, H.; Voges, H. W.; Hamamoto, T.; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H. J.; Garbe, D.; Paulus, W. Phenol Derivatives in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, New York, 2002.
      (c) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1, Ed.: Negishi, E.-I., Wiley-Interscience, New York, 2002, p. 1097.
      (d) Tyman, J. H. P. Synthetic and Natural Phenols, Elsevier, New York, 1996.
      (e) Liao, S.; Zhang, G.; Cao, H.; Chen, B.; Li, W.; Wu, X.; Feng, Y. Chin. J. Org. Chem. 2018, 38, 1549.
      (f) Lin, W.; Cai, Q.; Zheng, C.; Huang, Z.; Shi, D. Chin. J. Org. Chem. 2017, 37, 2094.
      (g) Li, Z.; Kang, S.; Chen, L.; Wang, Y.; Li, J. Chin. J. Org. Chem. 2016, 36, 1143.

    2. [2]

      Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.  doi: 10.1021/cr900184e

    3. [3]

      Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912.  doi: 10.1039/c1cs15085e

    4. [4]

      Thirunavukkarasu, V. S.; Kozhushkov, S. I.; Ackermann, L. Chem. Commun. 2014, 50, 29.  doi: 10.1039/C3CC47028H

    5. [5]

      Newhouse, T.; Baran, P. S. Angew. Chem. Int. Ed. 2011, 50, 3362.  doi: 10.1002/anie.201006368

    6. [6]

      Liang, Y.-F.; Jiao, N. Acc. Chem. Res. 2017, 50, 1640.  doi: 10.1021/acs.accounts.7b00108

    7. [7]

      Mandal, S.; Bera, T.; Dubey, G.; Saha, J.; Laha, J. K. ACS Catal. 2018, 8, 5085.  doi: 10.1021/acscatal.8b00743

    8. [8]

      (a) Huang, Z.; Dong, G. Acc. Chem. Res. 2017, 50, 465.
      (b) Hartwig, J. F. Acc. Chem. Res. 2017, 50, 549.
      (c) Kozlowski, M. C. Acc. Chem. Res. 2017, 50, 638.

    9. [9]

      For selected recent examples, see:
      (a) Raghuvanshi, K.; Zell, D.; Ackermann, L. Org. Lett. 2017, 19, 1278.
      (b) Raghuvanshi, K.; Rauch, K.; Ackermann, L. Chem.-Eur. J. 2015, 21, 1790.
      (c) Hao, X.-Q.; Chen, L.-J.; Ren, B.; Li, L.-Y.; Yang, X.-Y.; Gong, J.-F.; Niu, J.-L.; Song M.-P. Org. Lett. 2014, 16, 1104.
      (d) Shi, S.; Kuang, C. J. Org. Chem. 2014, 79, 6105.
      (e) Zhang, C.; Sun, P. J. Org. Chem. 2014, 79, 8457.
      (f) Péron, F.; Fossey, C.; Sopkova-de Oliveira Santos, J.; Cailly, T.; Fabis, F. Chem.-Eur. J. 2014, 20, 7507.
      (g) Bhadra, S.; Dzik, W. I.; Gooßen, L. J. Angew. Chem., Int. Ed. 2013, 52, 2959.
      (h) Bhadra, S.; Matheis, C.; Katayev, D.; Gooßen, L. J. Angew. Chem., Int. Ed. 2013, 52, 9279.
      (i) Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797.
      (j) Roane, J.; Daugulis, O. Org. Lett. 2013, 15, 5842.
      (k) Eom, D.; Jeong, Y.; Kim, Y. R.; Lee, E.; Choi, W.; Lee, P. H. Org. Lett. 2013, 15, 5210.
      (l) Zhao, J.; Wang, Y.; He, Y.; Liu, L.; Zhu, Q. Org. Lett. 2012, 14, 1078.
      (m) Zhao, J.; Zhang, Q.; Liu, L.; He, Y.; Li, J.; Li, J.; Zhu, Q. Org. Lett. 2012, 14, 5362.
      (n) Li, W.; Sun, P. J. Org. Chem. 2012, 77, 8362.
      (o) Jiang, T.-S.; Wang, G.-W. J. Org. Chem. 2012, 77, 9504.
      (p) Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu L. J. Am. Chem. Soc. 2011, 133, 9250.
      (q) Anand, M.; Sunoj, R. B. Org. Lett. 2011, 13, 4802.
      (r) Wei, Y.; Yoshikai, N. Org. Lett. 2011, 13, 5504.
      (s) Wang, X.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203.
      (t) Wang, G.-W.; Yuan, T.-T. J. Org. Chem. 2010, 75, 476.

    10. [10]

      For selected reviews and recent examples, see:
      (a) Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27.
      (b) Tang, S.; Zeng, L.; Lei, A. J. Am. Chem. Soc. 2018, 140, 13128.
      (c) Ma, C.; Fang, P.; Mei, T.-S. ACS Catal. 2018, 8, 7179.
      (d) Sauermann, N.; Meyer, T. H.; Qiu, Y.; Ackermann, L. ACS Catal. 2018, 8, 7086.
      (e) Sauermann, N.; Meyer, T. H.; Ackermann, L. Chem.-Eur. J. 2018, 24, 16209.
      (f) Jiao, K.-J.; Li, Z.-M.; Xu, X.-T.; Zhang, L.-P.; Li, Y.-Q.; Zhang, K.; Mei, T.-S. Org. Chem. Front. 2018, 5, 2244.
      (g) Shao, A.; Li, N.; Gao, Y.; Zhan, J.; Chiang, C.-W.; Lei, A. Chin. J. Chem. 2018, 36, 619.
      (h) Yang, Q.-L.; Fang, P.; Mei, T.-S. Chin. J. Chem. 2018, 36, 338.
      (i) Jiao, K.-J.; Zhao, C.-Q.; Fang, P.; Mei, T.-S. Tetrahedron Lett. 2017, 58, 797.
      (j) Yuan, Y.; Chen, Y.; Tang, S.; Huang, Z.; Lei, A. Sci. Adv. 2018, 4, eaat5312.
      (k) Shrestha, A.; Lee, M.; Dunn, A. L.; Sanford, M. S. Org. Lett. 2018, 20, 204.
      (l) Sauermann, N.; Meyer, T. H.; Tian, C.; Ackermann, L. J. Am. Chem. Soc. 2017, 139, 18452.
      (m) Yang, Q.-L.; Li, Y.-Q.; Ma, C.; Fang, P.; Zhang, X.-J.; Mei, T.-S. J. Am. Chem. Soc. 2017, 139, 3293.
      (n) Li, Y.-Q.; Yang, Q.-L.; Fang, P.; Mei, T.-S.; Zhang, D. Org. Lett. 2017, 19, 2905.

    11. [11]

      A recent example: Zhang, Z.-J.; Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Org. Lett. 2014, 16, 3292.

    12. [12]

      (a) Jintoku, T.; Taniguchi, H.; Fujiwara, Y. Chem. Lett. 1987, 1865.
      (b) Jintoku, T.; Takaki, K.; Fujiwara, Y.; Fuchita Y.; Hiraki, K. Bull. Chem. Soc. Jpn. 1990, 63, 438.
      (c) Jintoku, T.; Nishimura, K.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1990, 1687.

    13. [13]

      Yamada, S.; Sakaguchi, S.; Ishii, Y. J. Mol. Catal. A Chem. 2007, 262, 48.  doi: 10.1016/j.molcata.2006.08.045

    14. [14]

      Yoneyama, T.; Crabtree, R. H. J. Mol. Catal. A: Chem. 1996, 108, 35.  doi: 10.1016/1381-1169(95)00289-8

    15. [15]

      Cook, A. K.; Sanford, M. S. J. Am. Chem. Soc. 2015, 137, 3109.  doi: 10.1021/jacs.5b00238

    16. [16]

      Gary, J. B.; Cook, A. K.; Sanford, M. S. ACS Catal. 2013, 3, 700.  doi: 10.1021/cs300786j

    17. [17]

      Shibahara, F.; Kinoshita, S.; Nozaki, K. Org. Lett. 2004, 6, 2437.  doi: 10.1021/ol049166l

    18. [18]

      Chen, C.-D.; Sheng, W.-B.; Shi, G.-J.; Guo, C.-C. J. Phys. Org. Chem. 2013, 26, 23.  doi: 10.1002/poc.v26.1

    19. [19]

      Casella, L.; Rigoni, L. J. Chem. Soc., Chem. Commun. 1985, 1668.
       

    20. [20]

      Réglier, M.; Amadeï, E.; Tadayoni, R.; Waegell, B. J. Chem. Soc., Chem. Commun. 1989, 447.
       

    21. [21]

      Cruse, R. W.; Kaderli, S.; Meyer, C. J.; Zuberbühler, A. D.; Karlin, K. D. J. Am. Chem. Soc. 1988, 110, 5020.  doi: 10.1021/ja00223a020

    22. [22]

      Reinaud, O.; Capdevielle, P.; Maumy, M. J. Chem. Soc., Chem. Commun. 1990, 566.
       

    23. [23]

      Takizawa, Y.; Tateishi, A.; Sugiyama, J.; Yoshida, H.; Yoshihara, N. J. Chem. Soc., Chem. Commun. 1991, 104.
       

    24. [24]

      Singh, B. K.; Jana, R. J. Org. Chem. 2016, 81, 831.  doi: 10.1021/acs.joc.5b02302

    25. [25]

      Chen, X.; Hao, X.-S.; Goodhue, C.-E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.  doi: 10.1021/ja061715q

    26. [26]

      (a) Valk, J.-M.; van Belzen, R.; Boersma, J.; Spek, A. L.; van Koten, G. J. Chem. Soc., Dalton Trans. 1994, 2293.
      (b) Valk, J.-M.; Boersma, J.; van Koten, G. Organometallics 1996, 15, 4366.

    27. [27]

      Zhang, Y.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654.  doi: 10.1021/ja907198n

    28. [28]

      Shan, G.; Yang, X.; Ma, L.; Rao, Y. Angew. Chem., Int. Ed. 2012, 51, 13070.  doi: 10.1002/anie.201207458

    29. [29]

      Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.  doi: 10.1021/ja031543m

    30. [30]

      Subba Reddy, B. V.; Umadevi, N.; Narasimhulu, G.; Yadav, J. S. Tetrahedron Lett. 2012, 53, 6091.  doi: 10.1016/j.tetlet.2012.08.124

    31. [31]

      Zhao, Q.; Poisson, T.; Pannecoucke, X.; Besset, T. Synthesis 2017, 49, 4808.  doi: 10.1055/s-0036-1590878

    32. [32]

      Gandeepan, P.; Ackermann, L. Chem 2018, 4, 199.  doi: 10.1016/j.chempr.2017.11.002

    33. [33]

      Chen, X.-Y.; Ozturk, S.; Sorensen, E. J. Org. Lett. 2017, 19, 6280.  doi: 10.1021/acs.orglett.7b02906

    34. [34]

      Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.  doi: 10.1021/ol0530272

    35. [35]

      Liang, Y.-F.; Wang, X.; Yuan, Y.; Liang, Y.; Li, X.; Jiao, N. ACS Catal. 2015, 5, 6148.  doi: 10.1021/acscatal.5b01700

    36. [36]

      Nguyen, T. H. L.; Gigant, N.; Delarue-Cochin, S.; Joseph, D. J. Org. Chem. 2016, 81, 1850.  doi: 10.1021/acs.joc.5b02614

    37. [37]

      Qian, C.; Lin, D.; Deng, Y.; Zhang, X.-Q.; Jiang, H.; Miao, G.; Tang, X.; Zeng, W. Org. Biomol. Chem. 2014, 12, 5866.  doi: 10.1039/C4OB00993B

    38. [38]

      Zhang, D.; Cui, X.; Yang, F.; Zhang, Q.; Zhu, Y.; Wu, Y. Org. Chem. Front. 2015, 2, 951.  doi: 10.1039/C5QO00120J

    39. [39]

      Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 4149.  doi: 10.1021/ol051486x

    40. [40]

      Irastorza, A.; Aizpurua, J. M.; Correa, A. Org. Lett. 2016, 18, 1080.  doi: 10.1021/acs.orglett.6b00195

    41. [41]

      Kim, S. H.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 5863.  doi: 10.1016/j.tetlet.2008.07.141

    42. [42]

      Dong, J.; Liu, P.; Sun, P. J. Org. Chem. 2015, 80, 2925.  doi: 10.1021/acs.joc.5b00167

    43. [43]

      Yamaguchi, T.; Yamaguchi, E.; Tada, N.; Itoh, A. Adv. Synth. Catal. 2015, 357, 2017.  doi: 10.1002/adsc.v357.9

    44. [44]

      Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790.  doi: 10.1021/ja0541940

    45. [45]

      Stowers, K. J.; Sanford, M. S. Org. Lett. 2009, 11, 4584.  doi: 10.1021/ol901820w

    46. [46]

      Powers, D. C.; Geibel, M. A. L.; Klein, J. E. M. N.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 17050.  doi: 10.1021/ja906935c

    47. [47]

      Powers, D. C.; Xiao, D. Y.; Geibel, M. A. L.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 14530.  doi: 10.1021/ja1054274

    48. [48]

      Yan, Y.; Feng, P.; Zheng, Q.-Z.; Liang, Y.-F.; Lu, J.-F.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 5827.  doi: 10.1002/anie.201300957

    49. [49]

      Desai, L. V; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285.  doi: 10.1021/ja8045519

    50. [50]

      Wang, G.-W.; Yuan, T.-T.; Wu, X.-L. J. Org. Chem. 2008, 73, 4717.  doi: 10.1021/jo8003088

    51. [51]

      Sun, Y.-H.; Sun, T.-Y.; Wu, Y.-D.; Zhang, X.; Rao, Y. Chem. Sci. 2016, 7, 2229.  doi: 10.1039/C5SC03905C

    52. [52]

      Yang, X.; Sun, Y.; Chen, Z.; Rao, Y. Adv. Synth. Catal. 2014, 356, 1625.  doi: 10.1002/adsc.v356.7

    53. [53]

      A review: Parasram, M.; Gevorgyan, V. Acc. Chem. Res. 2017, 50, 2038.

    54. [54]

      (a) Chernyak, N.; Dudnik, A. S.; Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 8270.
      (b) Huang, C.; Chernyak, N.; Dudnik, A. S.; Gevorgyan, V. Adv. Synth. Catal. 2011, 353, 1285.
      (c) Gulevich, A. V.; Melkonyan, F. S.; Sarkar, D.; Gevorgyan, V. J. Am. Chem. Soc. 2012, 134, 5528.

    55. [55]

      (a) Huang, C.; Ghavtadze, N.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 17630.
      (b) Huang, C.; Ghavtadze, N.; Godoi, B.; Gevorgyan, V. Chem.-Eur. J. 2012, 18, 9789.

    56. [56]

      Yang, Y.; Lin, Y.; Rao, Y. Org. Lett. 2012, 14, 2874.  doi: 10.1021/ol301104n

    57. [57]

      Ackermann, L.; Vicente, R.; Potukuchi, H. K.; Pirovano, V. Org. Lett. 2010, 12, 5032.  doi: 10.1021/ol102187e

    58. [58]

      Thirunavukkarasu, V. S.; Hubrich, J.; Ackermann, L. Org. Lett. 2012, 14, 4210.  doi: 10.1021/ol3018819

    59. [59]

      Yang, F.; Ackermann, L. Org. Lett. 2013, 15, 718.  doi: 10.1021/ol303520h

    60. [60]

      Thirunavukkarasu, V. S.; Ackermann, L. Org. Lett. 2012, 14, 6206.  doi: 10.1021/ol302956s

    61. [61]

      Shan, G.; Han, X.; Lin, Y.; Yu, S.; Rao, Y. Org. Biomol. Chem. 2013, 11, 2318.  doi: 10.1039/c3ob27457h

    62. [62]

      Kim, K.; Choe, H.; Jeong, Y.; Lee, J. H.; Hong, S. Org. Lett. 2015, 17, 2550.  doi: 10.1021/acs.orglett.5b01138

    63. [63]

      Yang, F.; Rauch, K.; Kettelhoit, K.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 11285.  doi: 10.1002/anie.201405647

    64. [64]

      Shome, S.; Singh, S. P. Tetrahedron Lett. 2017, 58, 3743.  doi: 10.1016/j.tetlet.2017.08.037

    65. [65]

      Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Org. Lett. 2012, 14, 728.  doi: 10.1021/ol203251s

    66. [66]

      Yang, X.; Shan, G.; Rao, Y. Org. Lett. 2013, 15, 2334.  doi: 10.1021/ol400437a

    67. [67]

      Liu, W.; Ackermann, L. Org. Lett. 2013, 15, 3484.  doi: 10.1021/ol401535k

    68. [68]

      Turlington, C. R.; Morris, J.; White, P. S.; Brennessel, W. W.; Jones, W. D.; Brookhart, M.; Templeton, J. L. Organometallics 2014, 33, 4442.  doi: 10.1021/om500660n

    69. [69]

      Wu, Q.; Yan, D.; Chen, Y.; Wang, T.; Xiong, F.; Wei, W.; Lu, Y.; Sun, W.-Y.; Li, J. J.; Zhao, J. Nat. Commun. 2017, 8, 14227.  doi: 10.1038/ncomms14227

    70. [70]

      Cook, A. K.; Emmert, M. H.; Sanford, M. S. Org. Lett. 2013, 15, 5428.  doi: 10.1021/ol4024248

    71. [71]

      For selected recent views on template-directed meta-selective C(sp2)—H functionalizations, see:
      (a) Mihai, M. T.; Genov, G. R.; Phipps, R. J. Chem. Soc. Rev. 2017, 47, 149.
      (b) Ping, L.; Chung, D. S.; Bouffard, J.; Lee, S.-G. Chem. Soc. Rev. 2017, 46, 4299.
      (c) Mihai, M. T.; Phipps, R. J. Synlett 2017, 28, 1011.
      (d) Dey, A.; Agasti, S.; Maiti, D. Org. Biomol. Chem. 2016, 14, 5440.
      (e) Yang, G.; Butt, N.; Zhang, W. Chin. J. Catal. 2016, 37, 98.
      (f) Yang, G.; Butt, N.; Zhang, W. Chin. J. Catal. 2016, 37, 98.
      (g) Ackermann, L.; Li, J. Nat. Chem. 2015, 7, 686.
      (h) Yang, J. Org. Biomol. Chem. 2015, 13, 1930.

    72. [72]

      (a) Bera, M.; Sahoo, S. K.; Maiti, D. ACS Catal. 2016, 6, 3575.
      (b) Maji, A.; Bhaskararao, B.; Singha, S.; Sunoj, R. B.; Maiti, D. Chem. Sci. 2016, 7, 3147.

    73. [73]

      Bag, S.; Patra, T.; Modak, A.; Deb, A.; Maity, S.; Dutta, U.; Dey, A.; Kancherla, R.; Maji, A.; Hazra, A.; Bera, M.; Maiti, D. J. Am. Chem. Soc. 2015, 137, 11888.  doi: 10.1021/jacs.5b06793

    74. [74]

      A review on template-directed para-selective C(sp2)–H functionalizations: Dey, A.; Maity, S.; Maiti, D. Chem. Commun. 2016, 52, 12398.

  • 加载中
    1. [1]

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    2. [2]

      Mengying XU , Wen LI , Junzhong MEI , Cheng ZHANG , Kannan Palanisamy , Lei LU , Lianpeng ZHANG , Peng WANG . Manganese-doped poly(1,5-diaminonaphthalene) based high-performance supercapacitors. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 387-397. doi: 10.11862/CJIC.20250211

    3. [3]

      Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543

    4. [4]

      Xinghao Cai , Chen Ma , Ying Kang , Yuqiang Ren , Xue Meng , Wei Lu , Shiming Fan , Shouxin Liu . Nickel-catalyzed C(sp2)–H alkynylation of free α-substituted benzylamines using a transient directing group. Chinese Chemical Letters, 2025, 36(10): 110901-. doi: 10.1016/j.cclet.2025.110901

    5. [5]

      Gaorong Wu , Tao Ma . Recent advanced in C–H borylation using BX3 with different directing group auxiliary. Chinese Chemical Letters, 2026, 37(3): 111739-. doi: 10.1016/j.cclet.2025.111739

    6. [6]

      Xiao Tang , Erik V. Van der Eycken , Liangliang Song . Transition metal-catalyzed C-H activation/annulation for the construction of unnatural amino acids and peptides. Chinese Chemical Letters, 2026, 37(2): 111678-. doi: 10.1016/j.cclet.2025.111678

    7. [7]

      Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007

    8. [8]

      Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361

    9. [9]

      Yajun Gao ,  Xinyu Yang ,  Jian Su ,  Zhizhong Li . A stable scandium(III) metal-organic framework with introduced nitrate ions for enhancing C2H6/C2H4 selectivity in the separation of MTO products. Chinese Journal of Structural Chemistry, 2025, 44(6): 100576-100576. doi: 10.1016/j.cjsc.2025.100576

    10. [10]

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    11. [11]

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