Chinese Journal of Organic Chemistry >
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)
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.
Jiantao Zhang , Yawen Deng , Nuolin Mo , Lianfen Chen . Advances in Radical Mediated 1,2-Aryl Migration Reactions of α,α-Diarylallyl Alcohols[J]. Chinese Journal of Organic Chemistry, 2023 , 43(2) : 426 -435 . DOI: 10.6023/cjoc202208028
| [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. |
/
| 〈 |
|
〉 |
