Chinese Journal of Organic Chemistry >
Progress in the Synthesis of Hydrobenzofurans from O-Cyclohexadienone-tethered 1,6-Enynes
Received date: 2021-05-15
Revised date: 2021-06-21
Online published: 2021-07-06
Supported by
National Natural Science Foundation of China(22001140); Natural Science Foundation of Shandong Province(ZR2020QB002)
Hydrobenzofurans are abundant in bioactive molecules, natural products and drug molecules. Transition-metal- catalyzed intramolecular or intermolecular C—H bond functionalization/cyclization cascade of O-linkered cyclohexadienone-tethered 1,6-enynes is an economic and efficient way to construct this skeleton. The progress in the synthesis of hydrobenzofurans from cyclohexadienone-tethered 1,6-enynes via C—H bond functionalization/cyclization cascade catalyzed by different transition-metals is discussed. The relevant reaction modes, mechanisms and the selection of ligands for chiral control are mainly introduced. Finally, the challenges and development prospects in this field are also prospected and discussed.
Zhiqing Li , Xiaoyang Qiu , Nan Meng , Zhuqing Liu . Progress in the Synthesis of Hydrobenzofurans from O-Cyclohexadienone-tethered 1,6-Enynes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(11) : 4306 -4319 . DOI: 10.6023/cjoc202105029
| [1] | (a) Al-Tel, T. H.; Srinivasulu, V.; Ramanathan, M.; Soares, N. C.; Sebastian, A.; Bolognesi, M. L.; Abu-Yousef, I. A.; Majdalawieh, A. Org. Biomol. Chem. 2020, 18, 8526. |
| [1] | (b) Shu, T.; Cossy, J. Chem. Soc. Rev. 2021, 50, 658. |
| [1] | (c) Reddy, C. R.; Yarlagadda, S.; Sridhar, B.; Reddy, B. V. S. Eur. J. Org. Chem. 2017, 2017, 5763. |
| [2] | (a) Chen, B.; He, C. Y.; Chu, W. D.; Liu, Q. Z. Org. Chem. Front. 2021, 8, 825. |
| [2] | (b) Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383. |
| [2] | (c) Canesi, S.; Maertens, G.; Ménard, M.-A. Synthesis 2014, 46, 1573. |
| [2] | (d) Yang, W.; Sun, Z.; Zhang, J.; Li, Z.; Deng, W. P. Org. Chem. Front. 2019, 37, 216. |
| [2] | (e) Kalstabakken, K. A.; Harned, A. M. Tetrahedron 2014, 70, 9571. |
| [3] | Tello-Aburto, R.; Harned, A. M. Org. Lett. 2009, 11, 3998. |
| [4] | (a) Wegner, J.; Ley, S. V.; Kirschning, A.; Hansen, A.-L.; Garcia, J. M.; Baxendale, I. R. Org. Lett. 2012, 14, 696. |
| [4] | (b) Zhao, K.; Cheng, G.-J.; Yang, H.; Shang, H.; Zhang, X.; Wu, Y.-D.; Tang, Y. Org. Lett. 2012, 14, 4878. |
| [4] | (c) Hexum, J. K.; Tello-Aburto, R.; Struntz, N. B.; Harned, A. M.; Harki, D. A. ACS Med. Chem. Lett. 2012, 3, 459. |
| [4] | (d) Zhong, Y.-H.; Luo, Y.-X.; Luo, N.-H. Chin. J. Synth. Chem. 2020, 28, 1012. (in Chinese) |
| [4] | (钟瑜红, 罗玉欣, 罗年华, 合成化学, 2020, 28, 1012.) |
| [4] | (e) Zhang, Z. Y.; Jiao, N. Chin. J. Org. Chem. 2020, 40, 1790. (in Chinese) |
| [4] | (张梓曜, 焦宁, 有机化学, 2020, 40, 1790.) |
| [4] | (f) Yang, M.; Cao, S. X.; He, Z. J. Chin. J. Org. Chem. 2019, 39, 2235. (in Chinese) |
| [4] | (杨梅, 曹仕轩, 贺峥杰, 有机化学, 2019, 39, 2235.) |
| [4] | (g) Shi, W. Y.; Xu, J. Q.; Mao, B. M.; Jia, H.; Huang, J. X.; Guo, H. C. Chin. J. Org. Chem. 2020, 40, 756. (in Chinese) |
| [4] | (史望宇, 徐嘉擎, 毛比明, 贾皓, 黄家兴, 郭红超, 有机化学, 2020, 40, 756.) |
| [5] | Anulakanapakorn, K.; Bunyapraphatsara, N.; Satayavivad, J. J. Sci. Soc. Thailand 1987, 13, 71. |
| [6] | Jetty, A.; Iyengar, D. S. Pharm. Biol. 2011, 38, 157. |
| [7] | Gao, Y.-P.; Shen, Y.-H.; Zhang, S.-D.; Tian, J.-M.; Zeng, H.-W.; Ye, J.; Li, H.-L.; Shan, L.; Zhang, W.-D. Org. Lett. 2012, 14, 1954. |
| [8] | Liu, Q.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2552. |
| [9] | Takizawa, S.; Nguyen, T. M.; Grossmann, A.; Enders, D.; Sasai, H. Angew. Chem., Int. Ed. 2012, 51, 5423. |
| [10] | (a) Wu, W.; Chen, T.; Chen, J.; Han, X. J. Org. Chem. 2018, 83, 1033. |
| [10] | (b) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. |
| [11] | Tello-Aburto, R.; Kalstabakken, K. A.; Harned, A. M. Org. Biomol. Chem. 2013, 11, 5596. |
| [12] | Murthy, A. S.; Donikela, S.; Reddy, C. S.; Chegondi, R. J. Org. Chem. 2015, 80, 5566. |
| [13] | Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 082. |
| [14] | Takenaka, K.; Mohanta, S. C.; Sasai, H. Angew. Chem., Int. Ed. 2014, 53, 4675. |
| [15] | Singh, A.; Shukla, R. K.; Volla, C. M. R. Chem. Commun. 2019, 55, 13442. |
| [16] | Zhao, W.-C.; Wang, X.; Feng, J.; Tian, P.; He, Z.-T. Tetrahedron 2021, 79, 131862. |
| [17] | Keilitz, J.; Newman, S. G.; Lautens, M. Org. Lett. 2013, 15, 1148. |
| [18] | He, Z. T.; Tian, B.; Fukui, Y.; Tong, X.; Tian, P.; Lin, G. Q. Angew. Chem., Int. Ed. 2013, 52, 5314. |
| [19] | Li, Q.-H.; Gao, D.; He, C.-Y.; Liao, Q.; Tan, Y.-X.; Wang, Y.-H.; Ding, R.; Lin, G.-Q.; Tian, P. Cell Rep. Phys. Sci. 2020, 1, 100222. |
| [20] | Connor, C. J. O.; Beckmann, H. S.; Spring, D. R. Chem. Soc. Rev. 2012, 41, 4444. |
| [21] | Fukui, Y.; Liu, P.; Liu, Q.; He, Z. T.; Wu, N. Y.; Tian, P.; Lin, G. Q. J. Am. Chem. Soc. 2014, 136, 15607. |
| [22] | Zhou, X. L.; Pan, Y.; Li, X. W. Angew. Chem., Int. Ed. 2017, 56, 8163. |
| [23] | Lu, H.; Fan, Z.; Xiong, C.; Zhang, A. Org. Lett. 2018, 20, 3065. |
| [24] | Tan, Y.-X.; Liu, X.-Y.; Zhang, S.-Q.; Xie, P.-P.; Wang, X.; Feng, K.-R.; Yang, S.-Q.; He, Z.-T.; Hong, X.; Tian, P.; Lin, G.-Q. CCS Chem. 2021, 3, 1582. |
| [25] | Gao, D.; Wang, F.; Liu, X. Y.; Feng, K. R.; Zhao, J. Y.; Wang, Y. H.; Yang, X. D.; Tian, P.; Lin, G. Q. Adv. Synth. Catal. 2020, 362, 4384. |
| [26] | Gollapelli, K. K.; Donikela, S.; Manjula, N.; Chegondi, R. ACS catal. 2018, 8, 1440. |
| [27] | (a) Schobert, H. Chem. Rev. 2014, 114, 1743. |
| [27] | (b) Shirakura, M.; Suginome, M. Angew. Chem., Int. Ed. 2010, 49, 3827. |
| [27] | (c) Sawano, T.; Ashouri, A.; Nishimura, T.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 18936. |
| [28] | Duan, C. L.; Tan, Y. X.; Zhang, J. L.; Yang, S.; Dong, H. Q.; Tian, P.; Lin, G. Q. Org. Lett. 2019, 21, 1690. |
| [29] | Teng, Q.; Thirupathi, N.; Tung, C. H.; Xu, Z. Chem. Sci. 2019, 10, 6863. |
| [30] | Teng, Q.; Mao, W.; Chen, D.; Wang, Z.; Tung, C. H.; Xu, Z. Angew. Chem., Int. Ed. 2020, 59, 2220. |
| [31] | Jiang, Y.; Li, P.; Wang, J.; Zhao, J.; Li, Y.; Zhang, Y.; Chang, J.; Liu, B.; Li, X. Org. Lett. 2020, 22, 438. |
| [32] | Su, L.; Dong, J.; Liu, L.; Sun, M.; Qiu, R.; Zhou, Y.; Yin, S. F. J. Am. Chem. Soc. 2016, 138, 12348. |
| [33] | Liu, P.; Fukui, Y.; Tian, P.; He, Z. T.; Sun, C. Y.; Wu, N. Y.; Lin, G. Q. J. Am. Chem. Soc. 2013, 135, 11700. |
| [34] | He, C.-Y.; Xie, L.-B.; Ding, R.; Tian, P.; Lin, G.-Q. Tetrahedron 2019, 75, 1682. |
| [35] | Anugu, R. R.; Chegondi, R. J. Org. Chem. 2017, 82, 6786. |
| [36] | Xu, G.; Liu, K.; Sun, J. T. Org. Lett. 2017, 19, 6440. |
| [37] | McCoull, W.; Augustin, M.; Blake, C.; Ertan, A.; Kilgour, E.; Krapp, S.; Moore, J. E.; Newcombe, N. J.; Packer, M. J.; Rees, A.; Revill, J.; Scott, J. S.; Selmi, N.; Gerhardt, S.; Ogg, D. J.; Steinbacherc, S.; Whittamorea, P. R. O. Med. Chem. Commun. 2014, 5, 57. |
| [38] | Pitts, C. R.; Lectka, T. Chem. Rev. 2014, 114, 7930. |
| [39] | Shu, T.; Zhao, L.; Li, S.; Chen, X. Y.; von Essen, C.; Rissanen, K.; Enders, D. Angew. Chem., Int. Ed. 2018, 57, 10985. |
| [40] | (a) Hoffmann-Roder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196. |
| [40] | (b) Ma, S. Chem. Rev. 2005, 105, 829. |
| [41] | He, C. Y.; Tan, Y. X.; Wang, X.; Ding, R.; Wang, Y. F.; Wang, F.; Gao, D.; Tian, P.; Lin, G. Q. Nat. Commun. 2020, 11, 4293. |
| [42] | Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326. |
| [43] | Cai, S.; Liu, Z.; Zhang, W.; Zhao, X.; Wang, D. Z. Angew. Chem., Int. Ed. 2011, 50, 11133. |
| [44] | (a) Talele, T. T. J. Med. Chem. 2016, 59, 8712. |
| [44] | (b) Peh, G.; Floreancig, P. E. Org. Lett. 2012, 14, 5614. |
| [45] | Munakala, A.; Gollapelli, K. K.; Nanubolu, J. B.; Chegondi, R. Org. Lett. 2020, 22, 7019. |
| [46] | (a) Wang, C. Synlett 2013, 24, 1606. |
| [46] | (b) Hu, Y.; Zhou, B.; Wang, C. Acc. Chem. Res. 2018, 51, 816. |
| [47] | Liu, B.; Li, J.; Hu, P.; Zhou, X.; Bai, D.; Li, X. ACS catal. 2018, 8, 9463. |
| [48] | Tan, Y. X.; Liu, X. Y.; Zhao, Y. S.; Tian, P.; Lin, G. Q. Org. Lett. 2019, 21, 5. |
| [49] | Jackson, E. P.; Malik, H. A.; Sormunen, G. J.; Baxter, R. D.; Liu, P.; Wang, H.; Shareef, A. R.; Montgomery, J. Acc. Chem. Res. 2015, 48, 1736. |
| [50] | Kumar, R.; Hoshimoto, Y.; Tamai, E.; Ohashi, M.; Ogoshi, S. Nat. Commun. 2017, 8, 32. |
| [51] | Tsujihara, T.; Tomeba, M.; Ohkubo-Sato, S.; Iwabuchi, K.; Koie, R.; Tada, N.; Tamura, S.; Takehara, T.; Suzuki, T.; Kawano, T. Tetrahedron Lett. 2019, 60, 151148. |
| [52] | Cabrera-Lobera, N.; Rodroguez-Salamanca, P.; Nieto-Carmona, J. C.; BuÇuel, E.; Cárdenas, D. J. Chem.-Eur. J. 2018, 24, 784. |
| [53] | Hong, Y. C.; Santhoshkumar, R.; Cheng, C. H. J. Chin. Chem. Soc. 2019, 66, 1221. |
| [54] | Schultz, A. G.; Plummer, M.; Taveras, A. G.; Kullnig, R. K. J. Am. Chem. Soc. 1988, 110, 5547. |
| [55] | (a) Zhu, S.; Pathigoolla, A.; Lowe, G.; Walsh, D. A.; Cooper, M.; Lewis, W.; Lam, H. W. Chem.-Eur. J. 2017, 23, 17598. |
| [55] | (b) Nair, A. M.; Kumar, S.; Volla, C. M. R. Adv. Synth. Catal. 2019, 361, 4983. |
| [55] | (c) Ma, X.-L.; Wang, Q.; Feng, X.-Y.; Mo, Z.-Y.; Pan, Y.-M.; Chen, Y.-Y.; Xin, M.; Xu, Y.-L. Green Chem. 2019, 21, 3547. |
| [56] | Mallick, R. K.; Dutta, S.; Vanjari, R.; Voituriez, A.; Sahoo, A. K. J. Org. Chem. 2019, 84, 10509. |
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