α-三氟甲基酮的合成及其脱氟转化反应研究进展
收稿日期: 2024-11-22
修回日期: 2024-12-05
网络出版日期: 2024-12-12
基金资助
国家自然科学基金(22161022)
Advances in the Synthesis of α-Trifluoromethyl Ketones and Their Application via Defluorinative Reactions
Received date: 2024-11-22
Revised date: 2024-12-05
Online published: 2024-12-12
Supported by
National Natural Science Foundation of China(22161022)
曹素芳 , 刘云云 , 万结平 . α-三氟甲基酮的合成及其脱氟转化反应研究进展[J]. 有机化学, 2025 , 45(1) : 86 -103 . DOI: 10.6023/cjoc202411018
α-Trifluoromethyl ketones are a class of useful compounds with versatile applications. Their synthetic application via the transformation of the C—F bonds is of particular interest by allowing the synthesis of organic compounds with diverse structures. Herein, the advances in the research areas of α-trifluoromethyl ketone synthesis and their defluorination reactions are reviewed. Discussion on the mechanisms of the typical reactions has also been provided, in hope of affording some guides to the chemistry of α-trifluoromethyl ketones in the synthetic methods toward themselves and their derivatives.
| [1] | (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. |
| [1] | (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. |
| [1] | (c) Meyer, F. Chem. Commun. 2016, 52, 3077. |
| [2] | (a) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432. |
| [2] | (b) Meanwell, N. A. J. Med. Chem. 2018, 61, 5822. |
| [2] | (c) Johnson, B. M.; Shu, Y.; Zhuo, X.; Meanwell, N. A. J. Med. Chem. 2020, 63, 6315. |
| [3] | (a) Yang, W.; Ma, D.; Zhou, Y.; Dong, X.; Lin, Z.; Sun, J. Angew. Chem., Int. Ed. 2018, 57, 12097. |
| [3] | (b) Liu, H.; Shen, Q. Org. Chem. Front. 2019, 6, 2324. |
| [3] | (c) Xiao, F.; Yuan, S.; Huang, H., Zhang, F.; Deng, G.-J. Org. Lett. 2019, 21, 8533. |
| [3] | (d) Yuan, X.; Zheng, M.-W.; Di, Z.-C.; Cui, Y.-S.; Zhuang, K.-Q.; Qin, L.-Z.; Fang, Z.; Qiu, J.-K.; Li, G.; Guo, K. Adv. Synth. Catal. 2019, 361, 1835. |
| [3] | (e) Zhang, Z.; Zhang, L.; Cao, Y.; Li, F.; Bai, G.; Liu, G.; Yang, Y.; Mo, F. Org. Lett. 2019, 21, 762. |
| [3] | (f) Hirano, K.; Saito, T.; Fujihira, Y.; Sedgwick, D. M.; Fustero, S.; Shibata, N. J. Org. Chem. 2020, 85, 7976. |
| [3] | (g) Yu, Q.; Liu, Y.; Wan, J.-P. Org. Chem. Front. 2020, 7, 2770. |
| [4] | (a) Muñoz, L.; Bosch, M. P.; Batllori, L.; Rosell, G.; Bosch, D.; Guerrero, A.; Avilla, J. Pest Manage. Sci. 2011, 67, 956. |
| [4] | (b) Ikeda, M.; Matsuzawa, T.; Morita, T.; Hosoya, T.; Yoshida, S. Chem.-Eur. J. 2020, 26, 12333. |
| [5] | (a) Goldberg, S.; Martin, C. L.; Fennema, E. G.; Kummer, D. A.; Nishimura, R. T.; Woods, C. R.; Wolin, R. L.; Jones, W. M.; Fourie, A. M.; Xue, X. US 20190382349, 2019. |
| [5] | (b) Kim, J.; Ahn, S.; Jeon, Y.; Park, D.; Yang, Y.-I.; Lee, D.; Lee, S.; Ahn, J.; Kim, J.; Nam, K.; Kang, S.; Seo, M.; Seo, M.; Seo, J.; Han, S.-J.; Kim, J. H.; Lee, S.; Choi, G.; Lee, Y. WO 2016016421, 2016. |
| [5] | (c) Resnick, L.; Topalov, G. T.; Belardi, J. K.; Flentge, C. A.; Hale, J. S.; Mareska, D. A. US 20200062714, 2020. |
| [6] | Umemoto, T. Chem. Rev. 1996, 96, 1757. |
| [7] | Novák, P.; Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2012, 134, 16167. |
| [8] | Langlois, B. R.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1991, 32, 7525. |
| [9] | Vil’, V. A.; Merkulova, V. M.; Ilovaisky, A. I.; Paveliev, S. A.; Nikishin, G. I.; Terent’ev, A. O. Org. Lett. 2021, 23, 5107. |
| [10] | Su, X.; Huang, H.; Yuan, Y.; Li, Y. Angew. Chem., Int. Ed. 2017, 56, 1338. |
| [11] | He, Z.; Zhang, R.; Hu, M.; Li, L.; Ni, C.; Hu, J. Chem. Sci. 2013, 4, 3478. |
| [12] | Gan, L.; Yu, Q.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2021, 86, 1231. |
| [13] | Xu, X.; Chen, H.; He, J.; Xu, H. Chin. J. Chem. 2017, 35, 1665. |
| [14] | Mao, K.; Lv, L.; Li, Z. J. Org. Chem. 2023, 88, 10137. |
| [15] | Wang, F.; Zhang, T.; Tu, H.-Y.; Zhang, X.-G. J. Org. Chem. 2017, 82, 5475. |
| [16] | Deb, A.; Manna, S.; Modak, A.; Patra, T.; Maity, S.; Maiti, D. Angew. Chem., Int. Ed. 2013, 52, 9747. |
| [17] | Wu, Y.-b.; Lu, G.-p.; Yuan, T.; Xu, Z.-b.; Wan, L.; Cai, C. Chem. Commun. 2016, 52, 13668. |
| [18] | Kawamoto, T.; Sasaki, R.; Kamimura, A. Angew. Chem., Int. Ed. 2017, 56, 1342. |
| [19] | Zhao, L.; Li, P.; Zhang, H.; Wang, L. Org. Chem. Front. 2019, 6, 87. |
| [20] | Garg, P.; Singh, A. Asian J. Org. Chem. 2019, 8, 849. |
| [21] | Ma, R.; Deng, Z.; Wang, K.-H.; Wang, J.; Huang, D.; Su, Y.; Hu, Y.; Lv, X. ACS Omega 2022, 7, 14357. |
| [22] | Chen, Z.; Duan, Y.; Sun, S.; Lin, B.; Liu, X.; Liu, P. J. Org. Chem. 2023, 88, 4687. |
| [23] | Xu, J.; Li, Y.; Zhu, X.; Lv, S.; Xu, Y.; Cheng, T.; Liu, G.; Liu, R. Org. Lett. 2023, 25, 6211. |
| [24] | Wang, Z.; Lin, J.-H.; Xiao, J.-C. Org. Lett. 2024, 26, 1980. |
| [25] | Maji, A.; Hazra, A.; Maiti, D. Org. Lett. 2014, 16, 4524. |
| [26] | Malpani, Y. R.; Biswas, B. K.; Han, H. S.; Jung, Y.-S.; Han, S. B. Org. Lett. 2018, 20, 1693. |
| [27] | Cloutier, M.; Roudias, M.; Paquin, J.-F. Org. Lett. 2019, 21, 3866. |
| [28] | Wang, H.; Shi, W.; Li, Y.; Yu, M.; Gao, Y.; Lei, A. CCS Chem. 2020, 3, 1710. |
| [29] | Ma, J. A.; Cahard, D. J. Org. Chem. 2003, 68, 8726. |
| [30] | Cantillo, D.; Frutos, O.; Rincón, J. A.; Mateos, C.; Kappe, C. O. Org. Lett. 2014, 16, 896. |
| [31] | Das, S.; Hashmi, A. S. K.; Schaub, T. Adv. Synth. Catal. 2019, 361, 720. |
| [32] | Wu, C.-Y.; Chen, X.-L.; Wang, H.-Y.; Yang, D.-S.; Zhuang, S.-Y.; Zhou, Y.; Yu, Z.-C.; Wu, Y.-D.; Geng, X.; Wu, A.-X. Org. Chem. Front. 2023, 10, 3741. |
| [33] | Zhou, P.; Lu, S.; Wu, X.; Zhong, W.; Xu, T. Org. Lett. 2023, 25, 2344. |
| [34] | Yu, X.; Maity, A.; Studer, A. Angew. Chem., Int. Ed. 2023, 62, e202310288. |
| [35] | Liu, G.; Shen, H.; Wang, Z. Org. Lett. 2024, 26, 1863. |
| [36] | Gao, G.; Li, Z. New J. Chem. 2023, 47, 6171. |
| [37] | Guan, Y.-Q.; Qiao, J.-F.; Liang, Y.-F. Chem. Commun. 2024, 60, 2405. |
| [38] | Wu, Y.; Zhang, B.; Zheng, Y.; Wang, Y.; Lei, X. RSC Adv. 2018, 8, 16019. |
| [39] | Lv, L.; Gao, G.; Luo, Y.; Mao, K.; Li, Z. J. Org. Chem. 2021, 86, 17197. |
| [40] | Gao, G.; Mao, K.; Lv, L.; Li, Z. Adv. Synth. Catal. 2022, 364, 1402. |
| [41] | Gao, G.; Lv, L.; Li, Z. Eur. J. Org. Chem. 2024, 27, e202301135. |
| [42] | Mao, K.; Ma, Y.; Lv, L.; Li, Z. Asian J. Org. Chem. 2022, 11, e202200334. |
| [43] | Xu, L.; Zhang, Q.; Xie, Q.; Huang, B.; Dai, J.-J.; Xu, J.; Xu, H.-J. Chem. Commun. 2018, 54, 4406. |
| [44] | He, S.-Y.; Yan, X.-W.; Tu, H.-Y.; Zhang, X.-G. Org. Chem. Front. 2021, 8, 4746. |
| [45] | Shen, X.-Q.; Wang, S.-Q.; Fan, D.; Zhang, X.-G.; Tu, H.-Y. J. Org. Chem. 2021, 86, 1591. |
| [46] | Du, X.; Zhang, W.-M.; Zhang, X.-G.; Tu, H.-Y. Adv. Synth. Catal. 2022, 364, 2546. |
| [47] | Dong, Z.; Zhang, H.; Wang, B.; Li, B. Org. Lett. 2023, 25, 4770. |
| [48] | Shu, S.; Wang, L.; Lv, L.; Li, Z. Asian J. Org. Chem. 2023, 12, e202300075. |
/
| 〈 |
|
〉 |