Chinese Journal of Organic Chemistry >
Recent Progress in Aryne Participated Dearomatization Reactions
Received date: 2020-09-03
Revised date: 2020-09-29
Online published: 2020-10-28
Supported by
the Fundamental Research Funds for the Central Universities at Beijing University of Chemical Technology.(XK1802-6)
Dearomatization reaction is one of the most popular research areas in organic chemistry. It could build highly functionalized three-dimensional molecules from readily available planar aromatic compounds. In recent years, arynes as reactive intermediates have been extensively investigated in dearomatization reactions, and a series of synthetic protocols have been reported. The mechanisms of the dearomatization reaction of azaarenes with arynes, the [4+2] cycloaddition dearomatization reactions of arynes with dienes, and the dearomatization of arynes in other pathways are reviewed. The insights and outlooks regarding this rapid developing field are also provided.
Qiang Yan , Rong Fan , Binbin Liu , Shuaisong Su , Bo Wang , Tuanli Yao , Jiajing Tan . Recent Progress in Aryne Participated Dearomatization Reactions[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 455 -470 . DOI: 10.6023/cjoc202009009
| [1] | Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752. |
| [2] | Lebrasseur, N.; Fan, G.-J.; Oxoby, M.; Looney, M.A.; Quideau, S. Tetrahedron 2005, 61, 1551. |
| [3] | Kohmoto, S.; Masu, H.; Tatsuno, C.; Kishikawa, K.; Yamamoto, M.; Yamaguchi, K. J. Chem. Soc., Perkin Trans. 1 2000, 4464. |
| [4] | Caruana, P.A.; Frontier, A.J. Tetrahedron 2004, 60, 10921. |
| [5] | (a) Zhuo, C.X.; Zhang, W.; You, S.L. Angew. Chem., Int. Ed. 2012, 51, 12662. |
| [5] | (b) Zhu, M.; Zhang, X.; You, S.-L. Chem. J. Chin. Univ. 2020, 41, 1407. (in Chinese) |
| [5] | 朱敏, 张霄, 游书力, 高学校化学学报, 2020, 41, 1407.). |
| [5] | (c) Wu, W.-T.; Zhang, L.; You, S.-L. Acta Chim. Sinica 2017, 75, 419. (in Chinese) |
| [5] | 吴文挺, 张立明, 游书力, 化学学报,2017, 75, 419.). |
| [6] | Fan, L.-X.; Liu, J.-J.; Bai, L.; Wang, Y.-Y.; Luan, X.-J. Angew. Chem., Int. Ed. 2017, 56, 14257. |
| [6] | (b) Bai, L.; Liu, J.-J.; Hu, W.-J.; Li, K.-Y.; Wang, Y.-Y.; Luan, X.-J. Angew. Chem., Int. Ed. 2018, 57, 5151. |
| [6] | (c) Nan, J.; Yuan, Y.-N.; Bai, L.; Liu, J.-J.; Luan, X.-J. Org. Lett. 2018, 20, 7731. |
| [6] | (d) Hu, W.-J.; Wang, H.; Bai, L.; Liu, J.-J.; Luan, X.-J. Org. Lett. 2018, 20, 880. |
| [6] | (e) Tan, B.-J.; Bai, L.; Ding, P.; Liu, J.-J.; Wang, Y.-Y.; Luan, X.-J. Angew. Chem., Int. Ed. 2019, 58, 1474. |
| [7] | Jeganmohan, M.; Cheng, C.-H. Chem. Commun. 2006, 2454. |
| [8] | Jeganmohan, M.; Bhuvaneswari, S.; Cheng, C.-H. Chem.-Asian J. 2010, 5, 153. |
| [9] | Nakano, H.; Tsugawa, R.; Fujita, R. Tetrahedron Lett. 2005, 46, 5677. |
| [10] | Liu, K.; Liu, L.-L.; Gu, C.-Z.; Dai, B.; He, L. RSC Adv. 2016, 6, 33606. |
| [11] | Tan, J.-J.; Liu, B.-B.; Su, S.-S. Org. Chem. Front. 2018, 5, 3093. |
| [12] | Bhunia, A.; Roy, T.; Pachfule, P.; Rajamohanan, P.R.; Biju, A.T. Angew. Chem., Int. Ed. 2013, 52, 10040. |
| [13] | Bhunia, A.; Porwal, D.; Gonnade, R.G.; Biju, A.T. Org. Lett. 2013, 15, 4620. |
| [14] | Liu, P.; Lei, M.; Hu, L. Tetrahedron 2013, 69, 10405. |
| [15] | Li, S.-J.; Wang, Y.; Xu, J.-K.; Xie, D.; Tian, S.-K.; Yu, Z.-X. Org. Lett. 2018, 20, 4545. |
| [16] | Rayabarapu, D.K.; Majumdar, K.K.; Sambaiah, T.; Cheng, C.H. J. Org. Chem. 2001, 66, 3646. |
| [17] | Rogness, D.C.; Markina, N.A.; Waldo, J.P.; Larock, R.C. J. Org. Chem. 2012, 77, 2743. |
| [18] | Cheng, B.; Wei, J.; Zu, B.; Zhao, J.-F.; Wang, T.-M.; Duan, X.-G.; Wang, R.-Q.; Li, Y.; Zhai, H.-B. J. Org. Chem. 2017, 82, 9410. |
| [19] | Hoye, T.R.; Baire, B.; Niu, D.; Willoughby, P.H.; Woods, B.P. Nature 2012, 490, 208. |
| [20] | Arora, S.; Zhang, J.; Pogula, V.; Hoye, T.R. Chem. Sci. 2019, 10, 9069. |
| [21] | Yamashita, Y.; Hayashi, T.; Masumura, M. Chem. Lett. 1980, 1133. |
| [22] | Zhao, J.; Wu, C.; Li, P.; Ai, W.; Chen, H.; Wang, C.; Larock, R.C.; Shi, F. J. Org. Chem. 2011, 76, 6837. |
| [23] | Huang, X.; Zhang, T. Tetrahedron Lett. 2008, 50, 208. |
| [24] | Xie, C.-S.; Zhang, Y.-H.; Xu, P.-X. Synlett 2008, 20, 3115. |
| [25] | Okuma, K.; Hirano, K.; Shioga, C.; Nagahora, N.; Shioji, K. Bull. Chem. Soc. Jpn. 2013, 86, 615. |
| [26] | Wittig, G. Org. Synth. 1959, 39, 75. |
| [27] | Giles, R. G. F.; Roos, G. H. P. J. Chem. Soc., Chem. Commun. 1975, 260. |
| [27] | Hillard, R. L. III; Vollhardt, K. P. C. J. Am. Chem. Soc. 1976, 98, 3579. |
| [27] | Smith, W.B. J. Phys. Org. Chem. 2005, 18, 477. |
| [28] | Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211. |
| [29] | Chen, Y.-L.; Zhang, H.-K.; Wong, W.-Y.; Lee, A. W. M. Tetrahedron Lett. 2002, 43, 2259. |
| [30] | Chen, Y.-L.; Sun, J.-Q.; Wei, X.; Wong, W.-Y.; Lee, A. W. M. J. Org. Chem. 2004, 69, 7190. |
| [31] | Chen, Y.-L.; Hau, C.-K.; Wang, H.; He, H.; Wong, M.-S.; Lee, A. W. M. J. Org. Chem. 2006, 71, 3512. |
| [32] | Pei, B.-J.; Chan, W.-H.; Lee, A. W. M. J. Org. Chem. 2010, 75, 7332. |
| [33] | Ikawa, T.; Nishiyama, T.; Nosaki, T.; Takagi, A.; Akai, S. Org. Lett. 2011, 13, 1730. |
| [34] | Ikawa, T.; Sun, J.; Takagi, A.; Akai, S. J. Org. Chem. 2020, 85, 3383. |
| [35] | Sumida, Y.; Kato, T.; Hosoya, T. Org. Lett. 2013, 15, 2806. |
| [36] | Cho, S.; Wang, Q. Tetrahedron 2018, 74, 3325. |
| [37] | Prévost, S.; Dezaire, A.; Escargueil, A. J. Org. Chem. 2018, 83, 4871. |
| [38] | Kitamura, K.; Asahina, K.; Nagai, Y.; Sugiyama, H.; Uekusa, H.; Hamura, T. Chem.-Eur. J. 2018, 24, 14034. |
| [39] | Takikawa, H.; Nishii, A.; Takiguchi, H.; Yagishita, H.; Tanaka, M.; Hirano, K.; Uchiyama, M.; Ohnori, K.; Suzuki, K. Angew. Chem., Int. Ed. 2020, 59, 12440. |
| [40] | Cant, A.A.; Bertrand, G. H. V.; Henderson, J.L.; Roberts, L.; Greaney, M.F. Angew. Chem., Int. Ed. 2009, 48, 5199. |
| [41] | Bhojgude, S.S.; Thangaraj, M.; Suresh, E.; Biju, A.T. Org. Lett. 2014, 16, 3576. |
| [42] | Matsumoto, T.; Hosoya, T.; Suzuki, K. J. Am. Chem. Soc. 1992, 114, 3568. |
| [43] | O’Keefe, B.M.; Mans, D.M.; Kaelin, D. E., Jr; Martin, S.F. J. Am. Chem. Soc. 2010, 132, 15528. |
| [44] | Sumida, Y.; Harada, R.; Kato-Sumida, T.; Johmoto, K.; Uekusa, H.; Hosoya, T. Org. Lett. 2014, 16, 6240. |
| [45] | Moschitto, M.J.; Anthony, D.R.; Lewis, C.A. J. Org. Chem. 2015, 80, 3339. |
| [46] | Feng, Y.; Liu, J.; Carrasco, Y.P.; MacMillan, J.B.; DeBrabander, J.K. J. Am. Chem. Soc. 2016, 138, 7130. |
| [47] | Karmakar, R.; Le, A.; Xie, P.-P.; Xia, Y.-Z.; Lee, D. Org. Lett. 2018, 20, 4168. |
| [48] | Zuo, Z.-J.; Wang, H.; Diao, Y.-X.; Ge, Y.-C.; Liu, J.-J.; Luan, X.-J. ACS Catal. 2018, 8, 11029. |
/
| 〈 |
|
〉 |
