Citation: Jia Qianfa, Li Yaqiong, Lin Yinhe. Recent Advances in Organocatalyzed Aromatization Reactions[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1502-1513. doi: 10.6023/cjoc202001011 shu

Recent Advances in Organocatalyzed Aromatization Reactions

Chongqing Key Laboratory of Inorganic Special Functional Materials, College of Chemistry and Chemical Engineering, Yangtze Normal University, Fuling, Chongqing 408100

Corresponding author: Lin Yinhe, 20170168@yznu.cn
Received Date: 6 January 2020
Revised Date: 16 February 2020
Available Online: 29 February 2020
Fund Project: the Yangtze Normal University 2017KYQD123Project supported by the Yangtze Normal University (Nos. 2017KYQD123, 2018QNRC17)the Yangtze Normal University 2018QNRC17

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Aromatic compounds possess a particular fragrance and are widely present in natural products and pharmaceuticals. Among them, benzenes are the most abundant substructures of commercially available small-molecule drugs. Therefore, a variety of synthetic methodologies for the construction of aromatic compounds have been pursued vigorously and some significant progresses have been achieved. The dominant methods are transition metal-catalyzed benzannulation of enynes with alkynes to construct the functionalized benzenes. The synthesis of substituted benzene derivatives receives constant attentions since the formation and development of organocatalysis. Compared to metal catalysis, the organocatalytic benzannulation reaction avoids the introduction of a direct group into the pre-existed arene ring and appears to be tolerant of a broad range of substrates. While organocatalysis has emerged as a promising green and effieient synthetic tool and attracted a great deal of attention from synthetic chemists. The development of organocatalyzed aromatization reactions from acyclic starting materials is featured.
- organocatalysis,
- aromatization,
- annulation,
- research progress
1. [1]
  (a) McGrath, N. A.; Brichacek, M.; Njardarson, J. T. J. Chem. Educ. 2010, 87, 1348.
  (b) Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N. Beilstein J. Org. Chem. 2011, 7, 442.
2. [2]
  Davis, R.; Markham, A.; Balfour, J. A. Drugs 1996, 51, 1019. doi: 10.2165/00003495-199651060-00010
3. [3]
  (a) O'Brien, W. M.; Bagby, G. F. Pharmacotherapy 1987, 7, 16.
  (b) Ricketts, A. P.; Lundy, K. M.; Seibel, S. B. Am. J. Vet. Res. 1998, 59, 1441.
  (c) Thau-Zuchman, O.; Shohami, E.; Alexandrovich, A. G.; Trembovler, V.; Leker, R. R. J. Neurotraum. 2012, 29, 375.
4. [4]
  (a) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
  (b) Brunel, J. M. Chem. Rev. 2005, 105, 857.
  (c) Schenker, S.; Zamfir, A.; Freund, M.; Tsogoeva, S. B. Eur. J. Org. Chem. 2011, 2011, 2209.
5. [5]
  (a) Calloway, N. O. Chem. Rev. 1935, 17, 327.
  (b) Tanaka, K. Transition-metal-mediated Aromatic Ring Construction, Wiley, Hoboken, NJ, 2013.
  (c) Sunke, R.; Nallapati, S. B.; Kumar, J. S.; Kumarb, K. S.; Pal, M. Org. Biomol. Chem. 2017, 15, 4042.
6. [6]
  (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
  (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
  (c) Kotha, S.; Misra, S.; Halder, S. Tetrahedron 2008, 64, 10775.
  (d) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
7. [7]
  (a) van Otterlo, W. A.; De Koning, C. B. Chem. Rev. 2009, 109, 3743.
  (b) Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970.
  (c) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313.
  (d) Gevorgyan, V.; Sadayori, N.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 8603.
8. [8]
  Ramachary, D. B.; Ramakumar, K.; Kishor, M. Tetrahedron Lett. 2005, 46, 7037. doi: 10.1016/j.tetlet.2005.08.051
9. [9]
  Ramachary, D. B.; Ramakumar, K.; Narayana, V. V. J. Org. Chem. 2007, 72, 1458. doi: 10.1021/jo0623639
10. [10]
  Hong, B. C.; Tseng, H. C.; Chen, S. H. Tetrahedron 2007, 63, 2840. doi: 10.1016/j.tet.2007.01.039
11. [11]
  Li, S. G.; Hu, X. Q.; Jia, Z. X.; Xu, P. F. Tetrahedron 2010, 66, 8557. doi: 10.1016/j.tet.2010.08.069
12. [12]
  Wang, H.; Li, L.; Lin, W.; Xu, P.; Huang, Z.; Shi, D. Org. Lett. 2012, 14, 4598. doi: 10.1021/ol302058g
13. [13]
  Song, X.; Zhang, X.; Zhang, S.; Li, H.; Wang, W. Chem.-Eur. J. 2012, 18, 9770. doi: 10.1002/chem.201201709
14. [14]
  Link, A.; Sparr, C. Angew. Chem., Int. Ed. 2014, 53, 1. doi: 10.1002/anie.201310509
15. [15]
  Fäseke, V. C.; Sparr, C. Angew. Chem., Int. Ed. 2016, 55, 7261. doi: 10.1002/anie.201602689
16. [16]
  Magar, K. B. S.; Xia, L.; Lee, Y. R. Chem. Commun. 2015, 51, 8592. doi: 10.1039/C5CC00623F
17. [17]
  Ponra, S.; Vitale, M. R.; Michelet, V.; Ratovelomanana-Vidal, V. J. Org. Chem. 2015, 80, 3250. doi: 10.1021/acs.joc.5b00353
18. [18]
  Jiang, L.; Li, H.; Zhou, J. F.; Yuan, M. W.; Li, H. L.; Chuan, Y. M.; Yuan, M. L. Synth. Commun. 2018, 48, 336. doi: 10.1080/00397911.2017.1402351
19. [19]
  Liu, J. Y.; Yang, X. C.; Liu, Z.; Luo, Y. C.; Lu, H.; Gu, Y. C.; Fang, R.; Xu, P. F. Org. Lett. 2019, 21, 5219. doi: 10.1021/acs.orglett.9b01828
20. [20]
  (a) Nair, V.; Pillai, A. N.; Beneesh, P. B.; Suresh, E. Org. Lett. 2005, 7, 4625.
  (b) Nair, V.; Vidya, N.; Biju, A. T.; Deepthi, A.; Abhilash, K. G.; Suresh, E. Tetrahedron 2006, 62, 10136.
21. [21]
  (a) Zhou, Q. F.; Yang, F.; Guo, Q. X.; Xue, S. Synlett 2007, 2073.
  (b) Hu, B.; Meng, L. G.; Liu, Y. L.; Liang, M.; Xue, S. Synthesis 2009, 24, 4137.
22. [22]
  Talhi, O.; Makhloufi-Chebli, M.; Pinto, D. C.; Hamdi, M.; Silva, A. M. Synlett 2013, 24, 2559. doi: 10.1055/s-0033-1339895
23. [23]
  Babu, G. N.; Ayalew, H. M.; Jain, S. Med. Chem. Res. 2014, 23, 2608. doi: 10.1007/s00044-013-0857-0
24. [24]
  Moliterno, M.; Cari, R.; Puglisi, A.; Antenucci, A.; Sperandio, C.; Moretti, E.; Di Sabato, A.; Salvio, R.; Bella, M. Angew. Chem., Int. Ed. 2016, 55, 6525. doi: 10.1002/anie.201601660
25. [25]
  Hu, Z.; Dong, J.; Men, Y.; Li, Y.; Xu, X. Chem. Commun. 2017, 53, 1739. doi: 10.1039/C6CC09430A
26. [26]
  (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
  (b) Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
  (c) Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691.
  (d) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511.
  (e) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485.
  (f) Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307.
  (g) Zhang, C.; Hooper, J. F.; Lupton, D. W. ACS Catal. 2017, 7, 2583.
  (h) Zhao, M.; Zhang, Y.-T.; Chen, J.; Zhou, L. Asian J. Org. Chem. 2018, 7, 54.
27. [27]
  Zhu, T. S.; Zheng, P. C.; Mou, C. L.; Yang, S.; Song, B. A.; Chi, Y. R. Nat. Commun. 2014, 5, 6.
28. [28]
  Zhu, T. S.; Mou, C. L.; Li, B. S.; Smetankova, M.; Song, B. A.; Chi, Y. R. J. Am. Chem. Soc. 2015, 137, 5658. doi: 10.1021/jacs.5b02219
29. [29]
  Huang, X.; Zhu, T.; Huang, Z.; Zhang, Y.; Jin, Z.; Zanoni, G.; Chi, Y. R. Org. Lett. 2017, 19, 6188. doi: 10.1021/acs.orglett.7b03102
30. [30]
  Wu, J.; Mou, C.; Chi, Y. R. Chin. J. Chem. 2018, 36, 333. doi: 10.1002/cjoc.201700773
31. [31]
  Zhu, T.; Liu, Y.; Smetankova, M.; Zhuo, S.; Mou, C.; Chai, H.; Jin, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2019, 58, 15778. doi: 10.1002/anie.201910183
32. [32]
  Hu, J. M.; Zhang, J. Q.; Sun, B. B.; Chen, J. B.; Yu, J. Q.; Yang, X. P.; Lv, H. P.; Wang, Z.; Wang, X. W. Org. Lett. 2019, 21, 8582. doi: 10.1021/acs.orglett.9b03178
33. [33]
  Candish, L.; Levensa, A.; Lupton, D. W. Chem. Sci. 2015, 6, 2366. doi: 10.1039/C4SC03726J
34. [34]
  Jia, Q.; Wang, J. Org. Lett. 2016, 18, 2212. doi: 10.1021/acs.orglett.6b00844
35. [35]
  Zhang, C. L.; Gao, Z. H.; Liang, Z. Q.; Ye, S. Adv. Synth. Catal. 2016, 358, 2862. doi: 10.1002/adsc.201600531
36. [36]
  Zhang, C. L.; Ye, S. Org. Lett. 2016, 18, 6408. doi: 10.1021/acs.orglett.6b03306
37. [37]
  Liu, J.; Das, D. K.; Zhang, G.; Yang, S.; Zhang, H.; Fang, X. Org. Lett. 2018, 20, 64. doi: 10.1021/acs.orglett.7b03358
38. [38]
  Liu, D.; Gao, Y.; Huang, J.; Fu, Z.; Huang, W. J. Org. Chem. 2018, 83, 14210. doi: 10.1021/acs.joc.8b02532
39. [39]
  Chen, K. Q.; Luo, Z.; Gao, Z. H.; Ye, S. Chem.-Eur. J. 2019, 25, 3253.
40. [40]
  Xu, K.; Li, W.; Zhu, S.; Zhu, T. Angew. Chem., Int. Ed. 2019, 58, 17625. doi: 10.1002/anie.201910049
41. [41]
  (a) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
  (b) Brunel, J. M. Chem. Rev. 2005, 105, 857.
  (c) Renzi, P. Org. Biomol. Chem. 2017, 15, 4506.
  (d) Witzig, R. M.; Lotter, D.; Fäseke, V. C.; Sparr, C. Chem.-Eur. J. 2017, 23, 12960.
  (e) Link, A.; Sparr, C. Chem. Soc. Rev. 2018, 47, 3804.
42. [42]
  Chen, Y. H.; Cheng, D. J.; Zhang, J.; Wang, Y.; Liu, X. Y.; Tan, B. J. Am. Chem. Soc. 2015, 137, 15062. doi: 10.1021/jacs.5b10152
43. [43]
  Chen, Y. H.; Qi, L. W.; Fang, F.; Tan, B. Angew. Chem., Int. Ed. 2017, 56, 16308. doi: 10.1002/anie.201710537
44. [44]
  Gao, H.; Xu, Q. L.; Keene, C.; Yousufuddin, M.; Ess, D. H.; Kürti, L. Angew. Chem., Int. Ed. 2016, 55, 566. doi: 10.1002/anie.201508419
45. [45]
  Wang, J. Z.; Zhou, J.; Xu, C.; Sun, H.; Kürti, L.; Xu, Q. L. J. Am. Chem. Soc. 2016, 138, 5202. doi: 10.1021/jacs.6b01458
46. [46]
  Saha, S.; Banerjee, A.; Maji, M. S. Org. Lett. 2018, 20, 6920. doi: 10.1021/acs.orglett.8b03063
47. [47]
  Lu, D. L.; Chen, Y. H.; Xiang, S. H.; Yu, P.; Tan, B.; Li, S. Org. Lett. 2019, 21, 6000. doi: 10.1021/acs.orglett.9b02143
48. [48]
  Liu, L.; Wei, L.; Zhang, J. Adv. Synth. Catal. 2010, 352, 1920. doi: 10.1002/adsc.201000286
49. [49]
  Zheng, X.; Lv, L.; Lu, S.; Wang, W.; Li, Z. Org. Lett. 2014, 16, 5156. doi: 10.1021/ol5025053
50. [50]
  Bu, M. J.; Lu, G. P.; Cai, C. Org. Chem. Front. 2016, 3, 630. doi: 10.1039/C6QO00020G
51. [51]
  Reddy, C. R.; Dilipkumar, U.; Shravya, R. Chem. Commun. 2017, 53, 1904. doi: 10.1039/C6CC09108C
52. [52]
  Xiao, T.; Dong, X.; Tang, Y.; Zhou, L. Adv. Synth. Catal. 2012, 354, 3195. doi: 10.1002/adsc.201200569
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