自由基介导的α,α-二芳基烯丙醇1,2-芳基迁移反应研究进展
收稿日期: 2022-08-21
修回日期: 2022-10-07
网络出版日期: 2022-11-08
基金资助
广东石油化工学院人才引进计划(2019rc048); 国家自然科学基金(22002139); 广东省基础与应用基础研究基金(2019A1515110550)
Advances in Radical Mediated 1,2-Aryl Migration Reactions of α,α-Diarylallyl Alcohols
Received date: 2022-08-21
Revised date: 2022-10-07
Online published: 2022-11-08
Supported by
Projects of Talents Recruitment of Guangdong University of Petrochemical Technology(2019rc048); National Natural Science Foundation of China(22002139); Guangdong Basic and Applied Basic Research Foundation(2019A1515110550)
张建涛 , 邓雅文 , 莫诺琳 , 陈莲芬 . 自由基介导的α,α-二芳基烯丙醇1,2-芳基迁移反应研究进展[J]. 有机化学, 2023 , 43(2) : 426 -435 . DOI: 10.6023/cjoc202208028
As widely used building blocks, allyl alcohols can directly participate in the synthesis reaction without pre-functionalization. In recent years, the migration reaction of allyl alcohols has received great attention, and such reactions are often realized by semipinacol or neophyl rearrangement, providing a powerful strategy for the synthesis of various important carbonyl compounds. The latest progress of radical-initiated group migration reactions involving diaryl allyl alcohols as synthons systematically is reviewed, the scope, limitations and some mechanisms of the reaction are discussed, and the challenges and future development trends in this field are prospected.
| [1] | (a) Zhang, D.; Zhang, Y.; Wu, H.; Gong, L. Angew. Chem., Int. Ed. 2019, 58, 7450. |
| [1] | (b) Zhang, X.; Zhang, Z.; Song, J.; Wang, Z. Chem. Sci. 2020, 11, 7921. |
| [1] | (c) Guo, G.; Yuan, Y.; Wan, S.; Cao, X.; Sun, Y.; Huo, C. Org. Chem. Front. 2021, 8, 2990. |
| [1] | (d) Xing, Y.; Li, C.; Meng, J.; Zhang, Z.; Wang, X.; Wang, Z.; Ye, Y.; Sun, K. Adv. Synth. Catal. 2021, 363, 3913. |
| [2] | (a) Li, H.; Zhang, F.; Tu, Y.; Zhang, Q.; Chen, Z.; Chen, Z.; Li, J. Chem. Sci. 2011, 2, 1839. |
| [2] | (b) Wang, B.; Tu, Y.-Q. Acc. Chem. Res. 2011, 44, 1207. |
| [2] | (c) Chai, Z.; Rainey, T. J. J. Am. Chem. Soc. 2012, 134, 3615. |
| [2] | (d) Liu, Y.; Tse, Y.; Kwong, F.; Yeung, Y. ACS Catal. 2017, 7, 4435. |
| [3] | (a) Wu, P.; Wu, K.; Wang, L.; Yu, Z. Org. Lett. 2017, 19, 5450. |
| [3] | (b) Weng, W.-Z.; Zhang, B. Chem.-Eur. J. 2018, 24, 10934. |
| [3] | (c) Fang, J.; Dong, W.-L.; Xu, G.-Q.; Xu, P.-F. Org. Lett. 2019, 21, 4480. |
| [3] | (d) Tian, T.; Wang, X.; Lv, L.; Li, Z. Chem. Commun. 2020, 56, 14637. |
| [4] | (a) Chen, Z.; Bai, W.; Wang, S.; Yang, B.; Tu, Y.; Zhang, F. Angew. Chem., Int. Ed. 2013, 52, 9781. |
| [4] | (b) Kang, J.; Tu, Y.; Dong, J.; Chen, C.; Zhou, J.; Ding, T.; Zai, J.; Chen, Z.; Zhang, S. Org. Lett. 2019, 21, 2536. |
| [5] | Liu, X.; Xiong, F.; Huang, X.; Xu, L.; Li, P.; Wu, X. Angew. Chem., Int. Ed. 2013, 52, 6962. |
| [6] | Egami, H.; Shimizu, R.; Usui, Y.; Sodeoka, M. Chem. Commun. 2013, 49, 7346. |
| [7] | Huang, H.; Yan, H.; Gao, G.; Yang, C.; Xia, W. Asian J. Org. Chem. 2015, 4, 674. |
| [8] | Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683. |
| [9] | Cai, S; Tian, Y.; Zhang, J.; Liu, Z.; Lu, M; Weng, W.; Huang, M. Adv. Synth. Catal. 2018, 360, 4084. |
| [10] | Wang, H.; Xu, Q.; Yu, S. Org. Chem. Front. 2018, 5, 2224. |
| [11] | Guan, Z.; Wang, H.; Huang, Y.; Wang, Y.; Wang, S.; Lei, A. Org. Lett. 2019, 21, 4619. |
| [12] | Zhang, Y.; Ren, Z.; Liu, Y.; Wang, Z.; Li, Z. Eur. J. Org. Chem. 2020, 2020, 5192. |
| [13] | Liu, K.; Jin, Q.; Chen, S.; Liu, P. RSC Adv. 2017, 7, 1546. |
| [14] | (a) Wu, G.; Deng, Y.; Wu, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 10510. |
| [14] | (b) Qi, L.; Li, R.; Yao, X.; Zhen, Q.; Ye, P.; Shao, Y.; Chen, J. J. Org. Chem. 2020, 85, 1097. |
| [14] | (c) Gao, Y.; Quan, Y.; Li, Z.; Gao, L.; Zhang, Z.; Zou, X.; Yan, R.; Qu, Y.; Guo, K. Org. Lett. 2021, 23, 183. |
| [15] | Bunescu, A.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2015, 54, 3132. |
| [16] | Chu, X; Meng, H.; Zi, Y.; Xu, X.; Ji, S. Org. Chem. Front. 2015, 2, 216. |
| [17] | Li, Y.; Liu, B.; Li, H.; Wang, Q.; Li, J. Chem. Commun. 2015, 51, 1024. |
| [18] | Wang, Q.; Chen, Z.; Zhou, C.; Xiong, B.; Zhang, P.; Yang, C; Liu, Y.; Zhou, Q. Tetrahedron Lett. 2018, 59, 4551. |
| [19] | (a) Setzer, P.; Beauseigneur, A.; Pearson-Long, M. S. M.; Bertus, P. Angew. Chem., Int. Ed. 2010, 49, 8691. |
| [19] | (b) Huang, S. L.; K?tzner, L.; De, C. K.; List, B. J. Am. Chem. Soc. 2015, 137, 3446. |
| [20] | Zheng, L.; Huang, H.; Yang, C.; Xia, W. Org. Lett. 2015, 17, 1034. |
| [21] | Li, Y.; Leng, Y.; Wang, S.; Gao, Y.; Lv, H.; Chang, J.; Wu, Y.; Wu, Y. Appl. Organomet. Chem. 2018, 32, 4407. |
| [22] | Sarkar, S.; Banerjee, A.; Yao, W.; Patterson, E. V.; Ngai, M. ACS Catal. 2019, 9, 10358. |
| [23] | Pan, C.; Ni, Q.; Fu, Y.; Yu, J. J. Org. Chem. 2017, 82, 7683. |
| [24] | Chu, X.; Meng, H.; Zi, Y.; Xu, X.; Ji, S. Chem. Commun. 2014, 50, 9718. |
| [25] | Chu, X.; Meng, H.; Zi, Y.; Xu, X.; Ji, S. Chem.-Eur. J. 2014, 20, 17198. |
| [26] | Zhao, J.; Fang, H.; Song, R.; Zhou, J.; Han, J.; Pan, Y. Chem. Commun. 2015, 51, 599. |
| [27] | Song, R.; Tu, Y.; Zhu, D.; Zhang, F.; Wang, S. Chem. Commun. 2015, 51, 749. |
| [28] | (a) Smith, L. H. S.; Coote, S. C.; Sneddon, H. F.; Procter, D. J. Angew. Chem., Int. Ed. 2010, 49, 5832. |
| [28] | (b) Wojaczynska, E.; Wojaczynski, J. Chem. Rev. 2010, 110, 4303. |
| [29] | Lu, M; Qin, H; Lin, Z.; Huang, M.; Weng, W.; Cai, S. Org. Lett. 2018, 20, 7611. |
| [30] | Lin, Z.; Lu, M.; Liu, B.; Gao, J.; Huang, M.; Gan, Z.; Cai, S. New J. Chem. 2020, 44, 16031. |
| [31] | Zhu, Z.; Chen, X.; Liu, S.; Zhang, J.; Shen, X. Eur. J. Org. Chem. 2021, 2021, 4927. |
| [32] | (a) Dong, X.; Wang, W.; Li, H.; Xu, Q.; Ye, L.; Li, X.; Zhao, Z.; Li, X. Org. Chem. Front. 2021, 8, 3260. |
| [32] | (b) Victoria-Miguel, J.; García-Santos, W. H.; Cordero-Vargas, A. J. Org. Chem. 2022, 87, 9088. |
| [33] | Hu, W.; Sun, S.; Cheng, J. J. Org. Chem. 2016, 81, 4399. |
| [34] | Ge, D.; Luo, X; Tang, X.; Pang, C.; Wang, X.; Chu, X. Org. Biomol. Chem. 2021, 19, 2277. |
| [35] | (a) Banerjee, I.; Panda, T. K. Org. Biomol. Chem. 2021, 19, 6571. |
| [35] | (b) Hore, S.; Singh, R. P. Org. Biomol. Chem. 2022, 20, 498. |
| [36] | Chu, X.; Zi, Y.; Meng, H.; Xu, X.; Ji, S. Chem. Commun. 2014, 50, 7642. |
| [37] | Mi, X.; Wang, C.; Huang, M.; Wu, Y.; Wu, Y. Org. Biomol. Chem. 2014, 12, 8394. |
| [38] | Yin, Y.; Weng, W.; Sun, J.; Zhang, B. Org. Biomol. Chem. 2018, 16, 2356. |
| [39] | Wang, C.; Huang, X.; Liu, X.; Gao, S.; Zhao, B.; Yang, S. Chin. Chem. Lett. 2020, 31, 677. |
| [40] | Yu, Y.; Tambar, U. K. Chem. Sci. 2015, 6, 2777. |
| [41] | Li, Y.; Liu, B.; Ouyang, X.; Song, R.; Li, J. Org. Chem. Front. 2015, 2, 1457. |
| [42] | Huang, H.; Yan, H.; Yang, C.; Xia, W. Chem. Commun. 2015, 51, 4910. |
| [43] | Xu, P.; Hu, K.; Gu, Z.; Cheng, Y.; Zhu, C. Chem. Commun. 2015, 51, 7222. |
| [44] | Ge, D.; Wang, X.; Chu, X. Tetrahedron Lett. 2021, 70, 153002. |
| [45] | Hu, L.; Deng, Q.; Zhou, Y.; Zhang, X.; Xiong, Y. Tetrahedron 2020, 76, 130949. |
| [46] | (a) Matsuda, Y.; Tsuji, Y.; Fujihara, T. Chem. Commun. 2020, 56, 4648. |
| [46] | (b) Zhang, Y.; Guo, J.; Han, J.; Zhou, X.; Cao, W.; Fu, Z. Org. Biomol. Chem. 2021, 19, 6412. |
| [47] | Peng, H.; Yu, J.; Jiang, Y.; Cheng, J. Org. Biomol. Chem. 2015, 13, 10299. |
| [48] | Deng, Z.; Chen, C.; Cui, S. RSC Adv. 2016, 6, 93753. |
| [49] | Weng, W.; Sun, J.; Li, P.; Zhang, B. Chem. Eur. J. 2017, 23, 9752. |
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