Citation: Mao Pu, Zhu Junliang, Yuan Jinwei, Yang Liangru, Xiao Yongmei, Zhang Changsen. Recent Advances on the Catalytic Functionalization of Quinoxalin- 2(1H)-ones via C-H Bond Activation[J]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1529-1547. doi: 10.6023/cjoc201904025 shu

Recent Advances on the Catalytic Functionalization of Quinoxalin- 2(1H)-ones via C-H Bond Activation

  • Corresponding author: Yuan Jinwei, yuanjinweigs@126.com
  • Received Date: 10 April 2019
    Revised Date: 24 April 2019
    Available Online: 6 June 2019

    Fund Project: the Project of Youth Backbone Teachers of Henan University of Technology 2016003the Department of Henan Province Natural Science and Technology Foundation 172102210225the Program for Innovative Research Team from Zhengzhou 131PCXTD605Project supported by the Department of Henan Province Natural Science and Technology Foundation (Nos.172102210225 and 182102310675), the Natural Science Foundation in Henan Province Department of Education (No.17A150005), the Program for Innovative Research Team from Zhengzhou (No. 131PCXTD605), and the Project of Youth Backbone Teachers of Henan University of Technology (No.2016003)the Department of Henan Province Natural Science and Technology Foundation 182102310675the Natural Science Foundation in Henan Province Department of Education 17A150005

Figures(50)

  • Quinoxalin-2(1H)-ones are very important N-heterocyclic moieties found in natural products and pharmaceuticals, and exhibit an amazingly wide spectrum of biological properties. Numerous efforts have been devoted to the development of efficient approaches for the C-H bond activation and functionalization of quinoxalin-2(1H)-ones in recent years, including alkylation, benzylation, acylation, arylation, amination, amidation, phosphonation, and fluoroalkylation. The recent advances in this area are summarized and their reaction mechanisms are discussed.
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    1. [1]

      (a) Shi, L.; Zhou, H.; Wu, J.; Li, X. Mini-Rev. Org. Chem. 2015, 12, 96.
      (b) Pereira, J. A.; Pessoa, A. M.; Cordeiro, M. N. D. S.; Fernandes, R.; Prudêncio, C.; Noronha, J. P.; Vieira, M. Eur. J. Med. Chem. 2015, 97, 664.
      (c) Willardsen, J. A.; Dudley, D. A.; Cody, W. L.; Chi, L.; McClanahan, T. B.; Mertz, T. E.; Potoczak, R. E.; Narasimhan, L. S.; Holland, D. R.; Rapundalo, S. T.; Edmunds, J. J. J. Med. Chem. 2004, 47, 4089.

    2. [2]

      (a) Wagle, S.; Adhikari, A. V.; Kumari, N. S. Ind. J. Chem. 2008, 47, 439.
      (b) Badran, M. M.; Abouzid, K. A. M.; Hussein, M. H. M. Arch. Pharm. Res. 2003, 26, 107.
      (c) TenBrink, R. E.; Im, W. B.; Sethy, V. H.; Tang, A. H.; Carter, D. B. J. Med. Chem. 1994, 37, 758.

    3. [3]

      (a) Poulsen, T. B.; Jø rgensen, K. A. Chem. Rev. 2008, 108, 2903.
      (b) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550.

    4. [4]

      (a) Chen, X.; Li, J. J.; Hao, X. S.; Goodhu, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 78.
      (b) Chen, X.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 12634.
      (c) Zhang, Y.; Feng, J.; Li, C. J. J. Am. Chem. Soc. 2008, 130, 2900.
      (d) He, T.; Yu, L.; Zhang, L.; Wang, L.; Wang, M. Org. Lett. 2011, 13, 5016.
      (e) Guo, S.; Kumar, P. S.; Yang, M. Adv. Synth. Catal. 2017, 359, 2.
      (f) Jafarpour, F.; Darvishmolla, M. Org. Biomol. Chem. 2018, 16, 3396.

    5. [5]

      Nikam, S. S.; Sahasrabudhe, A. D.; Shastri, R. K.; Ramanathan, S. Synthesis 1983, 145.
       

    6. [6]

      (a) Velaparthi, S.; Brunsteiner, M.; Uddin, R.; Wan, B.; Franzblau, S. G.; Petukhov, P. A. J. Med. Chem. 2008, 51, 1999.
      (b) Wang, A.; Li, X.; Chen, C.; Wu, H.; Qi, Z.; Hu, C.; Yu, K.; Wu, J.; Liu, J.; Liu, X.; Hu, Z.; Wang, W.; Wang, W.; Wang, W.; Wang, L.; Wang, B.; Liu, Q.; Li, L.; Ge, J.; Ren, T.; Zhang, S.; Xia, R.; Liu, J.; Liu, Q. J. Med. Chem. 2017, 60, 8407.
      (c) Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207.

    7. [7]

      (a) Fujiwara, T.; O'Hagan, D. J. Fluorine Chem. 2014, 167, 16.
      (b) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.
      (c) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
      (d) Meanwell, N. A. J. Med. Chem. 2018, 61, 5822.

    8. [8]

      Liu, S.; Huang, Y.; Qing, F. L.; Xu, X. H. Org. Lett. 2018, 20, 5497.  doi: 10.1021/acs.orglett.8b02451

    9. [9]

      (a) Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597.
      (b) Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. J. Med. Chem. 2010, 53, 7902.
      (c) May, E. L.; Jacobson, A. E.; Mattson, M. V.; Traynor, J. R.; Woods, J. H.; Harris, L. S.; Bowman, E. R.; Aceto, M. D. J. Med. Chem. 2000, 43, 5030.
      (d) Fleming, F. F.; Zhang, Z. Y. Tetrahedron 2005, 61, 747.
      (e) López, R.; Palomo, C. Angew. Chem., Int. Ed. 2015, 54, 13170.

    10. [10]

      Yang, L.; Gao, P.; Duan, X. H.; Gu, Y. R.; Guo, L. N. Org. Lett. 2018, 20, 1034.  doi: 10.1021/acs.orglett.7b03984

    11. [11]

      (a) Martinez, C.; Alvarez R.; Aurrecoechea, J. M. Org. Lett. 2009, 11, 1083.
      (b) Ackermann, L.; Lygin A. V.; Hofmann, N. Angew Chem., Int. Ed. 2011, 123, 6503.
      (c) Zhou, B.; Yang Y.; Li, Y. Chem. Commun. 2012, 48, 5163.
      (d) Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew Chem., Int. Ed. 2009, 48, 5094.

    12. [12]

      Yuan, J.; Fu, J.; Yin, J.; Dong, Z.; Xiao, Y.; Mao, P.; Qu, L. Org. Chem. Front. 2018, 5, 2820.  doi: 10.1039/C8QO00731D

    13. [13]

      (a) Zou, Y. Q.; Chen, J. R.; Liu, X. P.; Lu, L. Q.; Davis, R. L.; Jø rgensen, K. A.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 784.
      (b) Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97.
      (c) Zhang, L.; Yi, H.; Wang, J.; Lei, A. Green Chem. 2016, 18, 5122.
      (d) Shi, Q.; Li, P.; Zhu, X.; Wang, L. Green Chem. 2016, 18, 4916.
      (e) Li, X.; Fang, X.; Zhuang, S.; Liu, P.; Sun, P. Org. Lett. 2017, 19, 3580.

    14. [14]

      Wei, W.; Wang, L.; Yue, H.; Bao, P.; Liu, W.; Hu, C.; Yang, D.; Wang, H. ACS Sustainable Chem. Eng. 2018, 6, 17252.  doi: 10.1021/acssuschemeng.8b04652

    15. [15]

      (a) Zhou, W.; Qian, P.; Zhao, J.; Fang, H.; Han, J.; Pan, Y. Org. Lett. 2015, 17, 1160.
      (b) Mallat, T.; Baiker, A. Chem. Rev. 2004, 104, 3037.
      (c) Zhang, S. Y.; Tu, Y. Q.; Fan, C. A.; Zhang, F. M.; Shi, L. Angew. Chem., Int. Ed. 2009, 48, 8761.
      (d) Hu, W.; Sun, S.; Cheng, J. J. Org. Chem. 2016, 81, 4399.
      (e) Meng, Y.; Guo, L. N.; Wang, H.; Duan, X. H. Chem. Commun. 2013, 49, 7540.

    16. [16]

      Fu, J.; Yuan, J.; Zhang, Y.; Xiao, Y.; Mao, P.; Diao, X.; Qu, L Org. Chem. Front. 2018, 5, 3382.  doi: 10.1039/C8QO00979A

    17. [17]

      (a) Bar, G.; Parsons, A. F. Chem. Soc. Rev. 2003, 32, 251.
      (b) Yamada, K.; Tomioka, K. Chem. Rev. 2008, 108, 2874.
      (c) Slater, K.; Friestad, G. K. J. Org. Chem. 2015, 80, 6432.

    18. [18]

      Zheng, D.; Studer, A. Org. Lett. 2019, 21, 325.  doi: 10.1021/acs.orglett.8b03849

    19. [19]

      (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
      (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
      (c) Nie, J.; Guo, H. C.; Cahard, D.; Ma, J. A. Chem. Rev. 2011, 111, 455.

    20. [20]

      Wang, L.; Zhang, Y.; Li, F.; Hao, X.; Zhang, H. Y.; Zhao, J. Adv. Synth. Catal. 2018, 360, 3969.  doi: 10.1002/adsc.v360.20

    21. [21]

      (a) Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626.
      (b) Xu, Y.; Aoki, J.; Shimizu, K.; Umezu-Goto, M.; Hama, K.; Takanezawa, Y.; Yu, S.; Mills, G. B.; Arai, H.; Qian, L.; Prestwich, G. D. J. Med. Chem. 2005, 48, 3319.
      (c) Fujikawa, K.; Fujioka, Y.; Kobayashi, A.; Amii, H. Org. Lett. 2011, 13, 5560.

    22. [22]

      Hong, G.; Yuan, J.; Fu, J.; Pan, G.; Pan, Z.; Wang, Z.; Yang, L.; Xiao, Y.; Mao, P.; Zhang, X. Org. Chem. Front. 2019, 6, 1173.  doi: 10.1039/C9QO00105K

    23. [23]

      (a) Lawrence, D. S.; Copper, J. E.; Smith, C. D. J. Med. Chem. 2001, 44, 594.
      (b) Wu, B.; Yang, Y.; Qin, X.; Zhang, S.; Jing, C.; Zhu, C.; Ma, B. ChemMedChem 2013, 8, 1913.
      (c) Khattab, S. N.; Abdel Moneim, S. A. H.; Bekhit, A. A.; El Massry, A. M.; Hassan, S. Y.; El-Faham, A.; Ali Ahmed, H. E.; Amer, A. Eur. J. Med. Chem. 2015, 93, 308.
      (d) Kobayashi, Y.; Suzuki, Y.; Ogata, T.; Kimachi, T.; Takemoto, Y. Tetrahedron Lett. 2014, 55, 3299.

    24. [24]

      Hu, L.; Yuan, J.; Fu, J.; Zhang, T.; Gao, L.; Xiao, Y.; Mao, P.; Qu, L. Eur. J. Org. Chem. 2018, 2018, 4113.  doi: 10.1002/ejoc.201800697

    25. [25]

      (a) Piras, S.; Loriga, M.; Carta, A.; Paglietti, G.; Costi, M. P.; Ferrari, S. J. Heterocycl. Chem. 2006, 43, 541.
      (b) Kucybała, Z.; Pączkowski, J. J. Photochem. Photobiol. A 1999, 128, 135.
      (c) Honda, H.; Shibusawa, Y.; Taniguchi, J.; Matsuda, H.; Kondod, M.; Kumasaka, K.; Miwa, T.; Notoya, Y.; Shindo, H. Vascul. Pharmacol. 2005, 42, 163.
      d) Azuma, K.; Suzuki, S.; Uchiyama, S.; Kajiro, T.; Santa, T.; Imai, K. Photochem. Photobiol. Sci. 2003, 2, 443.

    26. [26]

      (a) Wei, Y.; Hu, P.; Zhang, M.; Su, W. Chem. Rev. 2017, 117, 8864.
      (b) Rodriguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030.

    27. [27]

      Zeng, X.; Liu, C.; Wang, X.; Zhang, J.; Wang, X.; Hu, Y. Org. Biomol. Chem. 2017, 15, 8929.  doi: 10.1039/C7OB02187A

    28. [28]

      (a) Chen, J.; Wan, M.; Hua, J.; Sun, Y.; Lv, Z.; Li, W.; Liu, L. Org. Biomol. Chem. 2015, 13, 11561.
      (b) Chen, X.; Cui, X.; Wu, Y. Org. Lett. 2016, 18, 2411.
      (c) Liu, J. Q.; Shen, X. Y.; Liu, Z. H.; Wang, X. S. Org. Biomol. Chem. 2017, 15, 6314.
      (d) Jafarpour, F.; Abbasnia, M. J. Org. Chem. 2016, 81, 11982.

    29. [29]

      Yuan, J. W.; Fu, J. H.; Liu, S. N.; Xiao, Y. M.; Mao, P.; Qu, L. B. Org. Biomol. Chem. 2018, 16, 3203.  doi: 10.1039/C8OB00206A

    30. [30]

      (a) Gao, Y.; Lu, W.; Liu, P.; Sun, P.; J. Org. Chem. 2016, 81, 2482.
      (b) Li, X.; Fang, X.; Zhuang, S.; Liu, P.; Sun, P. Org. Lett. 2017, 19, 3580.

    31. [31]

      Xie, L. Y.; Peng, S.; Fan, T. G.; Liu, Y. F.; Sun, M.; Jiang, L. L.; Wang, X. X.; Cao, Z.; He, W. M. Sci. China Chem. 2019, 62, 460.  doi: 10.1007/s11426-018-9446-1

    32. [32]

      (a) Myers, M. R.; He, W.; Hanney, B.; Setzer, N.; Maguire, M. P.; Zulli, A.; Bilder, G.; Galzcinski, H.; Amin, D.; Needle, S.; Spada, A. P. Bioorg. Med. Chem. Lett. 2003, 13, 3091.
      (b) He, W.; Myers, M. R.; Hanney, B.; Spada, A. P.; Bilder, G.; Galzcinski, H.; Amin, D.; Needle, S.; Page, K.; Jayyosi, Z.; Perrone, M. H. Bioorg. Med. Chem. Lett. 2003, 13, 3097.
      (c) Aoki, K.; Koseki, J.; Takeda, S.; Aburada, M.; Miyamoto, K. Chem. Pharm. Bull. 2007, 55, 922.

    33. [33]

      (a) Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
      (b) Lei, F.; Chen, Y. J.; Sui, Y.; Liu, L.; Wang, D. Synlett 2003, 1160.

    34. [34]

      Han, Y. Y.; Wu, Z. J.; Zhang, X. M.; Yuan, W. C. Tetrahedron Lett. 2010, 51, 2023.  doi: 10.1016/j.tetlet.2010.02.031

    35. [35]

      (a) Hussain, S.; Pareen, S.; Hao, X.; Zhang, S.; Wang, W.; Qin, X.; Yang, Y.; Chen, X.; Zhu, S.; Zhu, C.; Ma, B. Eur. J. Med. Chem. 2014, 80, 383.
      (b) Yin, K.; Zhang, R. Org. Lett. 2017, 19, 1530.

    36. [36]

      (a) Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97.
      (b) Keshari, T.; Yadav, V. K.; Srivastava, V. P.; Yadav, L. D. S. Green Chem. 2014, 16, 3986.
      (c) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Soc. Rev. 2016, 45, 2044.

    37. [37]

      Wang, L.; Bao, P.; Liu, W.; Liu, S.; Hu, C.; Yue, H.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189.  doi: 10.6023/cjoc201807014

    38. [38]

      Jung, H. I.; Lee, J. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2018, 39, 1003.  doi: 10.1002/bkcs.2018.39.issue-8

    39. [39]

      Carrr, A.; Brion, J. D.; Messaoudi, S.; Alami, M. Org. Lett. 2013, 15, 5606.  doi: 10.1021/ol4028946

    40. [40]

      (a) Demir, A. S.; Reis, O.; Emrullahoglu, M. J. Org. Chem. 2003, 68, 578.
      (b) Dickschat, A.; Studer, A. Org. Lett. 2010, 12, 3972.
      (c) Yan, G. B.; Yang, M. H.; Wu, X. M. Org. Biomol. Chem. 2013, 11, 7999.
      (d) Yuan, J. W.; Yang, L. R.; Yin, Q. Y.; Mao, P.; Qu, L. B. RSC Adv. 2016, 6, 35936.

    41. [41]

      Ramesh, B.; Reddy, C. R.; Kumar, G. G.; Reddy, B. S. Tetrahedron Lett. 2018, 59, 628.  doi: 10.1016/j.tetlet.2017.12.085

    42. [42]

      (a) Surry, D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
      (b) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
      (c) Callonnec, F. L.; Fouquet, E.; Felpin, F. X. Org. Lett. 2011, 13, 2646.
      (d) Honraedt, A.; Callonnec, F. L.; Grognec, E. L.; Fernandez, V.; Felpin, F. X. J. Org. Chem. 2013, 78, 4604.

    43. [43]

      Yuan, J.; Liu, S.; Qu, L. Adv. Synth. Catal. 2017, 359, 4197.  doi: 10.1002/adsc.v359.23

    44. [44]

      Yin, K.; Zhang, R. Synlett 2018, 29, 597.  doi: 10.1055/s-0036-1589139

    45. [45]

      (a) Yang, Y.; Li, R.; Zhao, Y.; Zhao, D.; Shi, Z. J. Am. Chem. Soc. 2016, 138, 8734.
      (b) Liu, C.; Wang, Q. Org. Lett. 2016, 18, 5118.
      (c) Zhou, B.; Hou, W.; Yang, Y.; Feng, H.; Li, Y. Org. Lett. 2014, 16, 1322.
      (d) Li, P.; Cheng, G.; Zhang, H.; Xu, X.; Gao, J.; Cui, X. J. Org. Chem. 2014, 79, 8156.

    46. [46]

      Yin, K.; Zhang, R. Org. Lett. 2017, 19, 1530.  doi: 10.1021/acs.orglett.7b00310

    47. [47]

      (a) Hofmann, J.; Jasch, H.; Heinrich, M. R. J. Org. Chem. 2014, 79, 2314.
      (b) Jiang, T.; Chen, S. Y.; Zhuang, H.; Zeng, R. S.; Zou, J. P. Tetrahedron Lett. 2014, 55, 4549.

    48. [48]

      (a) Cui, J.; Jia, Q.; Feng, R.; Liu, S.; He, T.; Zhang, C. Org. Lett. 2014, 16, 1442.
      (b) Shen, H.; Li, J.; Liu, Q.; Pan, J.; Huang, R.; Xiong, Y. J. Org. Chem. 2015, 80, 7212.
      (c) Zheng, C.; Wang, Y.; Fan, R. Org. Lett. 2015, 17, 916.

    49. [49]

      Paul, S.; Ha, J. H.; Park, G. E.; Lee, Y. R. Adv. Synth. Catal. 2017, 359, 1515.  doi: 10.1002/adsc.v359.9

    50. [50]

      Paul, S.; Khanal, H. D.; Clinton, C. D.; Kim, S. H.; Lee, Y. R. Org. Chem. Front. 2019, 6, 231.  doi: 10.1039/C8QO01250D

    51. [51]

      (a) Ghadage, R. V.; Shirote, P. J. J. Chem. Pharm. Res. 2011, 3, 260.
      (b) Galal, S. A.; Abdelsamie, A. S.; Tokuda, H.; Suzuki, N.; Lida, A.; ElHefnawi, M. M.; Ramadan, R. A.; Atta, M. H. E.; EI Diwani, H. I. Eur. J. Med. Chem. 2011, 46, 327.
      (c) Rangisetty, J. B.; Gupta, C. N. V. H. B.; Prasad, A. L.; Srinivas, P.; Sridhar, N.; Parimoo, P.; Veeranjaneyulu, A. J. Pharm. Pharmacol. 2001, 53, 1409.

    52. [52]

      Gulevskaya, A. V.; Burov, O. N.; Pozharskii, A. F.; Kletskii, M. E.; Korbukova, I. N. Tetrahedron 2008, 64, 696.  doi: 10.1016/j.tet.2007.11.029

    53. [53]

      Li, Y.; Gao, M.; Wang, L.; Cui, X. Org. Biomol. Chem. 2016, 14, 8428.  doi: 10.1039/C6OB01283C

    54. [54]

      Gupta, A.; Deshmukh, M. S.; Jain, N. J. Org. Chem. 2017, 82, 4784.  doi: 10.1021/acs.joc.7b00464

    55. [55]

      Wei, W.; Wang, L.; Bao, P.; Shao, Y.; Yue, H.; Yang, D.; Yang, X.; Zhao, X.; Wang, H. Org. Lett. 2018, 20, 7125.  doi: 10.1021/acs.orglett.8b03079

    56. [56]

      (a) Jiang, Y. Y.; Xu, K.; Zeng, C. C. Chem. Rev. 2018, 118, 4485.
      (b) Yoshida, J. I.; Shimizu, A.; Hayashi, R. Chem. Rev. 2018, 118, 4702.
      (c) Wu, Z. J.; Li, S. R.; Long, H.; Xu, H. Z. Chem. Commun. 2018, 54, 4601.
      (d) Shrestha, A.; Lee, M.; Duan, A. L.; Sanford, M. S. Org. Lett. 2018, 20, 204.

    57. [57]

      (a) Xu, F.; Li, Y. J.; Huang, C.; Xu, H. C. ACS Catal. 2018, 8, 3820.
      (b) Qian, P.; Su, J. H.; Wang, Y. K.; Bi, M. X.; Zha, Z. G.; Wang, Z. Y. J. Org. Chem. 2017, 82, 6434.
      (c) Sauermann, N.; Mei, R. H.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 5090.
      (d) Gao, X. L.; Wang, P.; Zeng, L.; Tang, S.; Lei, A. W. J. Am. Chem. Soc. 2018, 140, 4195.

    58. [58]

      Li, K. J.; Xu, K.; Liu, Y. G.; Zeng, C. C.; Sun, B. G. Adv. Synth. Catal. 2019, 361, 1033.  doi: 10.1002/adsc.v361.5

    59. [59]

      (a) Peng, J.; Xie, Z.; Chen, M.; Wang, J.; Zhu, Q. Org. Lett. 2014, 16, 4702.
      (b) Pan, C.; Jin, N.; Zhang, H.; Han, J.; Zhu, C. J. Org. Chem. 2014, 79, 9427.
      (c) Zhang, Z.; Kumar, R. K.; Li, G.; Wu, D.; Bi, X. Org. Lett. 2015, 17, 6190.
      (d) Xie, Z.; Peng, J.; Zhu, Q. Org. Chem. Front. 2016, 3, 82.
      (e) Wu, Z.; Xu, P.; Zhou, N.; Duan, Y.; Zhang, M.; Zhu, C. Chem. Commun. 2017, 53, 1045.
      (f) Kong, X.; Lin, L.; Xu, B. Adv. Synth. Catal. 2018, 360, 2801.

    60. [60]

      Yang, Q.; Yang, Z.; Tan, Y.; Zhao, J.; Sun, Q.; Zhang, H. Y.; Zhang, Y. Adv. Synth. Catal. 2019, 361, 1662.  doi: 10.1002/adsc.v361.7

    61. [61]

      (a) Dudash Jr, J.; Zhang, Y.; Moore, J. B.; Look, R.; Liang, Y.; Beavers, M. P.; Conway, B. R.; Rybczynski, P. J.; Demarest, K. T. Bioorg. Med. Chem. Lett. 2005, 15, 4790.
      (b) Fleischhauer, J.; Beckert, R.; Juttke, Y.; Hornig, D.; Gunther, W.; Birckner, E.; Grummt, U. W.; Goerls, H. Chem. Eur. J. 2009, 15, 12799.

    62. [62]

      (a) Rach, S. F.; Kühn, F. E. Chem. Rev. 2009, 109, 2061.
      (b) Zhang, Y.; Pan, L.; Zou, Y.; Xu, X.; Liu, Q. Chem. Commun. 2014, 50, 14334.
      (c) Xu, X.; Zhang, L.; Liu, X.; Pan, L.; Liu, Q. Angew. Chem., Int. Ed. 2013, 52, 9271.
      (d) Hu, Z.; Dong, J.; Men, Y.; Lin, Z.; Cai, J.; Xu, X. Angew. Chem., Int. Ed. 2017, 56, 1805.

    63. [63]

      Yuan, J.; Liu, S.; Xiao, Y.; Mao, P.; Yang, L.; Qu, L. Org. Biomol. Chem. 2019, 17, 876.  doi: 10.1039/C8OB03061H

    64. [64]

      Yuan, J.; Zhu, J.; Fu, J.; Yang, L.; Xiao, Y.; Mao, P.; Du, X.; Qu, L. Org. Chem. Front. 2019, 6, 925.  doi: 10.1039/C9QO00063A

    65. [65]

      Guo, T.; Wang, C. C.; Fu, X. H.; Liu, Y.; Zhang, P. K. Org. Biomol. Chem. 2019, 17, 3333.  doi: 10.1039/C9OB00294D

    66. [66]

      (a) Dang, Q.; Liu, Y.; Cashion, D. K.; Kasibhatla, S. R.; Jiang, T.; Taplin, F.; Jacintho, J. D.; Li, H.; Sun, Z.; Fan, Y.; Re, J. D.; Tian, F.; Li, W.; Gibson, T.; Lemus, R.; Poelje, P. D. J. Med. Chem. 2011, 54, 153.
      (b) Roush, R. F.; Nolan, E. M.; Lö hr, F.; Walsh, C. T. J. Am. Chem. Soc. 2008, 130, 3603.
      (c) Jeon, S. O.; Lee, J. Y. J. Mater. Chem. 2012, 22, 7239.

    67. [67]

      (a) Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250.
      (b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
      (c) Zhang, X.; Chen, K.; Shi, Z. J. Chem. Sci. 2014, 5, 2146.

    68. [68]

      Gao, M.; Li, Y.; Xie, L.; Chauvin, R.; Cui, X. Chem. Commun. 2016, 52, 2846.  doi: 10.1039/C5CC08049E

    69. [69]

      (a) Meggers, E. Chem. Commun. 2015, 51, 3290.
      (b) Cismesia, M. A.; Yoon, T. P. Chem. Sci. 2015, 6, 5426.
      (c) Ravelli, D.; Protri, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850.

    70. [70]

      Kim, Y.; Kim, D. Y. Tetrahedron Lett. 2018, 59, 2443.  doi: 10.1016/j.tetlet.2018.05.034

    71. [71]

      Nishio, T. J. Org. Chem. 1984, 49, 827.  doi: 10.1021/jo00179a015

    72. [72]

      Carr r, A.; Brion, J. D.; Alami, M.; Messaoudi, S. Adv. Synth. Catal. 2014, 356, 3821.  doi: 10.1002/adsc.v356.18

    73. [73]

      Yang, Q.; Zhang, Y.; Sun, Q.; Shang, K.; Zhang, H. Y.; Zhao, J. Adv. Synth. Catal. 2018, 360, 4509.  doi: 10.1002/adsc.201801076

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