镍催化炔烃的立体选择性芳基-二氟烷基化反应
Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes
Received date: 2022-03-28
Revised date: 2022-04-24
Online published: 2022-05-07
孙奇 , 孙泽颖 , 俞泽 , 王光伟 . 镍催化炔烃的立体选择性芳基-二氟烷基化反应[J]. 有机化学, 2022 , 42(8) : 2515 -2520 . DOI: 10.6023/cjoc202203054
A nickel-catalyzed aryl-difluoroalkylation of alkynes is developed. A series of trisubstituted fluoroalkenes can be obtained in a highly stereoselective manner by mixing of simple starting materials alkynes, ethyl bromodifluoroacetate, and arylboronic acids in the presence of nickel catalyst. This method features low-cost catalyst, mild reaction conditions, and excellent functional group compatibility.
| [1] | (a) Bo?hm, H. J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Mu?ller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637. |
| [1] | (b) O’Hagan, D. Chem. Soc. Rev. 2008, 37, 308. |
| [1] | (c) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315. |
| [2] | (a) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470. |
| [2] | (b) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475. |
| [3] | Li, K.; Zhang, X.; Chen, J.; Gao, Y.; Yang, C.; Zhang, K.; Zhou, Y.; Fan, B. Org. Lett. 2019, 21, 9914. |
| [4] | (a) Xu, Y.; Qian, L.; Pontsler, A. V.; McIntyre, T. M.; Prestwich, G. D. Tetrahedron 2004, 60, 43. |
| [4] | (b) O’Hagan, D. Chem. Soc. Rev. 2008, 37, 308. |
| [4] | (c) Meanwell, N. A. J. Med. Chem. 2011, 54, 2529. |
| [5] | (a) Feng, Z.; Min, Q.-Q.; Xiao, Y.-L.; Zhang, B.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 1669. |
| [5] | (b) Xiao, Y.-L.; Guo, W.-H.; He, G.-Z.; Pan, Q.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 9909. |
| [6] | (a) Wang, X.; Zhao, S.; Li, J.; Zhu, D.; Guo, M.; Tang, X.; Wang, G. Org. Lett. 2017, 19, 4187. |
| [6] | (b) Feng, X.; Wang, X.; Chen, H.; Tang, X.; Guo, M.; Zhao, W.; Wang, G. Org. Biomol. Chem. 2018, 16, 2841. |
| [7] | (a) Chinchilla, R.; Na?jera, C. Chem. Rev. 2014, 114, 1783. |
| [7] | (b) Zhang, C.; Li, N.; Li, X.; Chang, H.; Liu, Q.; Wei, W. Chin. J. Org. Chem. 2014, 34, 81. (in Chinese) |
| [7] | (张聪霞, 李娜娜, 李兴, 常宏宏, 刘强, 魏文珑, 有机化学, 2014, 34, 81.) |
| [7] | (c) Zhao, F.; Jia, X.; Wang, D.; Fei, C.; Wu, C.; Wang, J.; Liu, H. Chin. J. Org. Chem. 2017, 37, 284. (in Chinese) |
| [7] | (赵飞, 贾秀稳, 王东萍, 费朝丽, 吴成林, 王江, 柳红, 有机化学, 2017, 37, 284.) |
| [7] | (d) Ghosh, S.; Lai, D.; Hajra, A. Org. Biomol. Chem. 2020, 18, 7948. |
| [7] | (e) Corpas, J.; Mauleón, P.; Arrayás, R. G.; Carretero, J. C. ACS Catal. 2021, 11, 7513. |
| [8] | (a) Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabo, K. J. Org. Lett. 2012, 14, 2882. |
| [8] | (b) Xu, T.; Cheung, C. W.; Hu, X. Angew. Chem., Int. Ed. 2014, 53, 4910. |
| [9] | Li, Z.; García-Domínguez, A.; Nevado, C. J. Am. Chem. Soc. 2015, 137, 11610. |
| [10] | (a) Wang, Q.; He, Y.-T.; Zhao, J.-H.; Qiu, Y.-F.; Zheng, L.; Hu, J.-Y.; Yang, Y.-C.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2016, 18, 2664. |
| [10] | (b) He, Y.-T.; Wang, Q.; Li, L.-H.; Liu, X.-Y.; Xu, P.-F.; Liang, Y.-M. Org. Lett. 2015, 17, 5188. |
| [11] | Upadhyaya, N. S.; Chaładaj, W. Adv. Synth. Catal. 2020, 362, 493. |
| [12] | (a) Wu, P.; Zheng, C.; Wang, X.; Wu, J.; Wu, F. Eur. J. Org. Chem. 2021, 9, 1420. |
| [12] | (b) Liang, J.; Huang, G.; Peng, P.; Zhang, T.; Wu, J.; Wu, F. Adv. Synth. Catal. 2018, 360, 2221. |
| [13] | (a) Galli, C.; Guarnieri, A.; Koch, H.; Mencarelli, P.; Rappaport, Z. J. Org. Chem. 1997, 62, 4072. |
| [13] | (b) Singer, L. A.; Chen, J. Tetrahedron Lett. 1969, 10, 4849. |
| [13] | (c) Evans, P. A.; Manangan, T. J. Org. Chem. 2000, 65, 4523. |
| [14] | Wang, Y.-F.; Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2005, 25, 8. (in Chinese) |
| [14] | (王晔峰, 邓维, 刘磊, 郭庆祥, 有机化学, 2005, 25, 8.) |
/
| 〈 |
|
〉 |