Chinese Journal of Organic Chemistry >
Recent Progress in Radical Involved Alkene Dialkylation
Received date: 2023-12-20
Revised date: 2024-02-06
Online published: 2024-02-28
Supported by
National Natural Science Foundation of China(22002063)
Difunctionalization of alkenes constitutes a critical route for alkene derivatization and construction of molecular complexities. Yet dialkylation of alkenes allows the continuous construction of two new C(sp3)—C(sp3) bonds which is one of the most effective ways for functional alkane synthesis. Because of the high reactivity of alkyl reagents, problems such as poor regioselectivity and side reactions always appear in alkene alkylation process. In recent ten years, with the further development in radical mediated reactions, significant progress has been seen in difunctionalization of alkenes through radical path. However, challenges still exist in the implement of high selectively dialkylation of alkenes. This review aims to give a comprehensive overview about the radical involved alkene dialkylated reaction. The regioselectivity control of this reaction is elaborated from three different reaction modes: intramolecular cyclization-intermolecular alkylation, alkyl radical addition-1,2-migrated alkylation of alkenyl boron ate complexes and three-components reaction of alkenes with disparate alkylated reagents.
Lingyi Lu , Xiaodong Qiu . Recent Progress in Radical Involved Alkene Dialkylation[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 1701 -1718 . DOI: 10.6023/cjoc202312020
| [1] | (a) Chen, J.; Guo, J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075. |
| [1] | (b) Wang, X.-X.; Lu, X.; Li, Y.; Wang, J.-W.; Fu, Y. Sci. China Chem. 2020, 63, 1586. |
| [1] | (c) He, Y.; Chen, J.; Jiang, X.; Zhu, S. Chin. J. Chem. 2022, 40, 651. |
| [1] | (d) Zhang, Z.; Bera, S.; Fan, C.; Hu, X. J. Am. Chem. Soc. 2022, 144, 7015. |
| [1] | (e) Yang, H.; Ye, Y. Top. Curr. Chem. 2023, 381, 23. |
| [1] | (f) Liao, G.; Shi, B.-F. Sci. Bull. 2023, 68, 462. |
| [2] | (a) Qi, X.; Diao, T. ACS Catal. 2020, 10, 8542. |
| [2] | (b) Derosa, J.; Apolinar, O.; Kang, T.; Tran, V. T.; Engle, K. M. Chem. Sci. 2020, 11, 4287. |
| [2] | (c) Luo, Y.-C.; Xu, C.; Zhang, X. Chin. J. Chem. 2020, 38, 1371. |
| [2] | (d) Zhu, S.; Zhao, X.; Li, H.; Chu, L. Chem. Soc. Rev. 2021, 50, 10836. |
| [2] | (e) Belal, M.; Li, Z.; Lu, X.; Yin, G. Sci. China: Chem. 2021, 64, 513. |
| [2] | (f) Gao, P.; Niu, Y.-J.; Yang, F.; Guo, L.-N.; Duan, X-H. Chem. Commun. 2022, 58, 730. |
| [2] | (g) Ke, Y.; Li, W.; Liu, W.; Kong, W. Sci. China: Chem. 2023, 66, 2951. |
| [3] | Phapale, V. B.; Bu?uel, E.; García-Iglesias, M.; Cárdenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790. |
| [4] | Guisán-Ceinos, M.; Soler-Yanes, R.; Collado-Sanz, D.; Phapale, V. B.; Bu?uel, E.; Cárdenas, D. J. Chem.-Eur. J. 2013, 19, 8405. |
| [5] | Kuang, Y.; Wang, X.; Anthony, D.; Diao, T. Chem. Commun. 2018, 54, 2558. |
| [6] | Nieto-Carmona, J. C.; Román, R. S.; Bu?uel, E.; Cárdenas, D. J. Eur. J. Org. Chem. 2022, e202200992. |
| [7] | Hewitt, K. A.; Herbert, C. A.; Jarvo, E. R. Org. Lett. 2022, 24, 6093. |
| [8] | Kischkewitz, M.; Okamoto, K.; Mück-Lichtenfeld, C.; Studer, A. Science 2017, 355, 936. |
| [9] | Tappin, N. D. C.; Gnagi-Lux, M.; Renaud, P. Chem.-Eur. J. 2018, 24, 11498. |
| [10] | Silvi, M.; Sandford, C.; Aggarwal. V. K. J. Am. Chem. Soc. 2017, 139, 5736. |
| [11] | Gerleve, C.; Kischkewitz, M.; Studer, A. Angew. Chem., Int. Ed. 2018, 57, 2441. |
| [12] | Davenport, R.; Silvi, M.; Noble, A.; Hosni, Z.; Fey, N.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2020, 59, 6525. |
| [13] | Zhang, F.; Liao, S.; Zhou, L.; Yang, K.; Wang, C.; Lou, Y.; Wang, C.; Song, Q. Chin. J. Chem. 2022, 40, 582. |
| [14] | Mizutani, K.; Shinokubo, H.; Oshima, K. Org. Lett. 2003, 5, 3959. |
| [15] | Terao, J.; Kato, Y.; Kambe, N. Chem. Asian J. 2008, 3, 1472. |
| [16] | Chierchia, M.; Xu, P.; Lovinger, G. J.; Morken, J. P. Angew. Chem., Int. Ed. 2019, 58, 14245. |
| [17] | Wang, X.-X.; Lu, X.; He, S.-J.; Fu, Y. Chem. Sci. 2020, 11, 7950. |
| [18] | Zhang, Z.; Zhu, L.; Li, C. Chin. J. Chem. 2019, 37, 452. |
| [19] | Cai, A.; Yan, W.; Zeng, X.; Zacate, S. B.; Chao, T. H.; Krause, J. A.; Cheng, M.-J.; Liu, W. Nat. Commun. 2021, 12, 3272. |
| [20] | Zhang, J. X.; Shu, W. Org. Lett. 2022, 24, 3844. |
| [21] | Lux, D. M.; Aryal, V.; Niroula, D.; Giri, R. Angew. Chem., Int. Ed. 2023, e202305522. |
| [22] | Derosa, J.; Puyl, V. A. V. D.; Tran, V. T.; Liu, M.; Engle, K. M. Chem. Sci. 2018, 9, 5278. |
| [23] | Yang, T.; Jiang, Y.; Luo, Y.; Lim, J. J. H.; Lan, Y.; Koh, M. J. J. Am. Chem. Soc. 2020, 142, 21410. |
| [24] | Xu, C.; Yang, Z.-F.; An, L.; Zhang, X. ACS Catal. 2019, 9, 8224. |
| [25] | Dhungana, R. K.; Sapkota, R. R.; Wickham, L. M.; Niroula, D.; Giri, R. J. Am. Chem. Soc. 2020, 142, 20930. |
| [26] | Ouyang, X.-H.; Li, Y.; Song, R.-J.; Hu, M.; Luo, S.; Li, J.-H. Sci. Adv. 2019, 5, eaav9839. |
| [27] | Duan, S.; Zi, Y.; Wang, L.; Cong, J.; Chen, W.; Li, M.; Zhang, H.; Yang, X.; Walsh, P. J. Chem. Sci. 2022, 13, 3740. |
| [28] | Ye, F.; Yang, Y.; Wang, W.; Yuan, W. Chem. Catal. 2023, 3, 100605. |
| [29] | Bao, Q.-F.; Xia, Y.; Li, M.; Wang, Y.-Z.; Liang, Y.-M. Org. Lett. 2020, 22, 7757. |
| [30] | Bao, Q.-F.; Li, M.; Xia, Y.; Wang, Y.-Z.; Zhou, Z.-Z.; Liang, Y.-M. Org. Lett. 2021, 23, 1107. |
| [31] | Sun, W.-H.; Zou, J.-Y.; Xu, X.-J.; Wang, J.-L.; Liu, M.-L.; Liu, X.-Y. Adv. Synth. Catal. 2022, 364, 2260. |
| [32] | Shen, Y.; Lei, N.; Lu, C.; Xi, D.; Geng, X.; Tao, P.; Su, Z.; Zheng, K. Chem. Sci. 2021, 12, 15399. |
/
| 〈 |
|
〉 |
