Chinese Journal of Organic Chemistry >
Visible Light Mediated Palladium-Catalyzed Hydrodebromination of Aliphatic α-Bromotrifluoromethyl Compounds
Received date: 2024-06-17
Revised date: 2024-09-22
Online published: 2024-10-18
Supported by
National Natural Science Foundation of China(21762053); Youth Science and Technology Talent Growth Project of Guizhou Provincial Department of Education(2017-191)
Due to its unique physicochemical properties, the trifluoromethyl group has been widely used in medicinal chemistry and materials science. Thus, the synthesis of organic compounds bearing trifluoromethyl groups has attracted considerable attention. However, the current methods for constructing aliphatic trifluoromethyl compounds are still very limited. In this paper, α-bromotrifluoromethyl compounds were used as raw materials and Pd(PPh3)4 was used as catalyst to achieve the hydrodebromination of alkyl α-trifluoromethyl bromides under visible light irradiation, generating a series of structurally diverse trifluoromethylated alkanes.
Jieqing Ou , Peizhen Qu , Liang Zhao . Visible Light Mediated Palladium-Catalyzed Hydrodebromination of Aliphatic α-Bromotrifluoromethyl Compounds[J]. Chinese Journal of Organic Chemistry, 2025 , 45(4) : 1334 -1341 . DOI: 10.6023/cjoc202406023
| [1] | (a) Mu?ller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. |
| [1] | (b) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305. |
| [1] | (c) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. |
| [1] | (d) Wang, J.; Sánchez-Roselló, M.; Acen?a, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432. |
| [1] | (e) Preshlock, S.; Tredwell, M.; Gouverneur, V. Chem. Rev. 2016, 116, 719. |
| [1] | (f) Luo, H.; Zhao, Y.; Wang, D.; Wang, M.; Shi, Z. Green Synth. Catal. 2020, 1, 134. |
| [1] | (g) Ge, C.; Chen, C. Green Synth. Catal. 2023, 4, 334. |
| [1] | (h) Gao, X.; He, X.; Zhang, X. Chin. J. Org. Chem. 2019, 39, 215 (in Chinese). |
| [1] | (高兴, 何旭, 张新刚, 有机化学, 2019, 39, 215.) |
| [1] | (i) Zhang, D.; Zhao, H.; Feng, X.; Gu, Y.; Zhang, X. Acta Chim. Sinica 2024, 82, 105 (in Chinese). |
| [1] | (张大伟, 赵海洋, 冯笑甜, 顾玉诚, 张新刚, 化学学报, 2024, 82, 105.) |
| [2] | (a) Nair, A. S.; Singh, A. K.; Kumar, A.; Kumar, S.; Sukumaran, S.; Koyiparambath, V. P.; Pappachen, L. K.; Rangarajan, T. M.; Kim, H.; Mathew, B. Processes 2022, 10, 2054. |
| [2] | (b) Ali, S.; Zhou, J. Eur. J. Med. Chem. 2023, 256, 115476. |
| [2] | (c) Zhu, W.; Wang, J.; Wang, S.; Gu, Z.; Ace?a, J. L.; Izawa, K.; Liu, H.; Soloshonok, V. A. J. Fluorine Chem. 2014, 167, 37. |
| [2] | (d) Brar, S. S. J. Am. Coll. Cardiol. 2017, 69, 186. |
| [3] | Wang, Y. T.; Yang, P. C.; Zhang, Y. F.; Sun, J. F. Eur. J. Med. Chem. 2024, 265, 116124. |
| [4] | Keam, S. J. Drugs 2023, 83, 547. |
| [5] | Syed, Y. Y. Drugs 2023, 83, 1537. |
| [6] | (a) Wallentin, C. J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. Am. Chem. Soc. 2012, 134, 8875. |
| [6] | (b) Zhu, L.; Wang, L. S.; Li, B.; Fu, B.; Zhang, C. P.; Li, W. Chem. Commun. 2016, 52, 6371. |
| [6] | (c) Wang, L.; Ma, Y.; Jiang, Y.; Lv, L.; Li, Z. Chem. Commun. 2021, 57, 7846. |
| [6] | (d) Wu, F. P.; Yuan, Y.; Wu, X. F. Angew. Chem., Int. Ed. 2021, 60, 25787. |
| [6] | (e) Ouyang, Y.; Tong, C. L.; Xu, X. H.; Qing, F. L. Org. Lett. 2020, 23, 346. |
| [6] | (f) Mao, T.; Ma, M. J.; Zhao, L.; Xue, D. P.; Yu, Y.; Gu, J.; He, C. Y. Chem. Commun. 2020, 56, 1815. |
| [7] | (a) Koller, R.; Stanek, K.; Stolz, D.; Aardoom, R.; Niedermann, K.; Togni, A. Angew. Chem., Int. Ed. 2009, 48, 4332. |
| [7] | (b) Tan, X.; Liu, Z.; Shen, H.; Zhang, P.; Zhang, Z.; Li, C. J. Am. Chem. Soc. 2017, 139, 12430. |
| [7] | (c) Shen, H.; Liu, Z.; Zhang, P.; Tan, X.; Zhang, Z.; Li, C. J. Am. Chem. Soc. 2017, 139, 9843. |
| [7] | (d) Kautzky, J. A.; Wang, T.; Evans, R. W.; MacMillan, D. W. C. J. Am. Chem. Soc. 2018, 140, 6522. |
| [7] | (e) Chen, Y.; Ma, G.; Gong, H. Org. Lett. 2018, 20, 4677. |
| [8] | (a) Gietter-Burch, A. A. S.; Devannah, V.; Watson, D. A. Org. Lett. 2017, 19, 2957. |
| [8] | (b) Liu, Z.; Xiao, H.; Zhang, B.; Shen, H.; Zhu, L.; Li, C. Angew. Chem., Int. Ed. 2019, 58, 2510. |
| [8] | (c) Sarver, P. J.; Bacauanu, V.; Schultz, D. M.; DiRocco, D. A.; Lam, Y. H.; Sherer, E. C.; MacMillan, D. W. C. Nat. Chem. 2020, 12, 459. |
| [8] | (d) He, J.; Nguyen, T. N.; Guo, S.; Cook, S. P. Org. Lett. 2021, 23, 702. |
| [9] | (a) Ma, B.; Chu, Z.; Huang, B.; Liu, Z.; Liu, L.; Zhang, J. Angew. Chem., Int. Ed. 2017, 56, 2749. |
| [9] | (b) Du, H. W.; Du, Y. D.; Zeng, X. W.; Shu, W. Angew. Chem., Int. Ed. 2023, 62, e202308732. |
| [9] | (c) Li, W.; Mao, T.; Yang, J. J.; Shang, M. C.; Li, X.; Wang, A. J.; Wang, P.; Zhao, L. Asian J. Org. Chem. 2023, 12, e202300329. |
| [9] | (d) Qin, T.; Xu, C.; Zhang, G.; Zhang, Q. Org. Chem. Front. 2023, 10, 1981. |
| [10] | Guo, P.; Tao, M.; Xu, W. W.; Wang, A. J.; Li, W.; Yao, Q.; Jie, T.; He, C. Y. Org. Lett. 2022, 24, 2143. |
| [11] | (a) Li, X.; Feng, Z.; Jiang, Z. X.; Zhang, X. Org. Lett. 2015, 17, 5570. |
| [11] | (b) Min, Y.; Sheng, J.; Yu, J. L.; Ni, S. X.; Ma, G.; Gong, H.; Wang, X. S. Angew. Chem., Int. Ed. 2021, 60, 9947. |
| [11] | (c) Zhou, P.; Li, X.; Wang, D.; Xu, T. Org. Lett. 2021, 23, 4683. |
| [11] | (d) Jin, R. X.; Wu, B. B.; Bian, K. J.; Yu, J. L.; Dai, J. C.; Zuo, Y. W.; Zhang, Y. F.; Wang, X. S. Nat. Commun. 2022, 13, 7035. |
| [11] | (e) Guo, W.; Cheng, L.; Ma, G.; Tong, W.; Wu, F. Org. Lett. 2022, 24, 1796. |
| [11] | (f) Wu, B. B.; Xu, J.; Bian, K. J.; Gao, Q.; Wang, X. S. J. Am. Chem. Soc. 2022, 144, 6543. |
| [11] | (g) Zhang, T.; Zuo, Y. W.; Jin, R. X.; Zhang, Y. F.; Wu, B. B.; Wang, X. S. Org. Lett. 2023, 25, 3578. |
| [11] | (h) Zhou, P.; Lu, S.; Wu, X.; Zhong, W.; Xu, T. Org. Lett. 2023, 25, 2344. |
| [11] | (i) Guo, P.; Pu, G.; Wang, G.; Zeng, L. Y.; Li, W. P.; Li, X.; Zhou, P. P.; He, C. Y. Org. Lett. 2024, 26, 3097. |
| [12] | Gavin, J. T.; Belli, R. G.; Roberts, C. C. J. Am. Chem. Soc. 2022, 144, 21431. |
| [13] | Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J. Am. Chem. Soc. 2002, 124, 906. |
| [14] | Liu, C.; Zhu, C.; Cai, Y.; Yang, Z.; Zeng, H.; Chen, F.; Jiang, H. Chem.-Eur. J. 2020, 26, 1953. |
| [15] | Zhou, Z. Z.; Zhao, J. H.; Gou, X. Y.; Chen, X. M.; Liang, Y. M. Org. Chem. Front. 2019, 6, 1649. |
| [16] | (a) Chuentragool, P.; Kurandina, D.; Gevorgyan, V. Angew. Chem., Int. Ed. 2019, 58, 11586. |
| [16] | (b) Kancherla, R.; Muralirajan, K.; Maity, B.; Zhu, C.; Krach, P. E.; Cavallo, L.; Rueping, M. Angew. Chem., Int. Ed. 2019, 58, 3412. |
| [16] | (c) Luo, Y. C.; Tong, F.F.; Zhang, Y.; He, C.Y.; Zhang, X. J. Am. Chem. Soc. 2021, 143, 13971. |
| [17] | Xue, J. H.; Li, Y.; Liu, Y.; Li, Q.; Wang, H. Angew. Chem., Int. Ed. 2024, 63, e202319030. |
| [18] | Kornfilt, D. J.; MacMillan, D. W. J. Am. Chem. Soc. 2019, 141, 6853. |
| [19] | Geniller, L.; Taillefer, M.; Jaroschik, F.; Prieto, A. ACS Catal. 2023, 13, 8624. |
| [20] | He, B.; Pan, Q.; Guo, Y.; Chen, Q.; Liu, C. Org. Lett. 2020, 22, 6552. |
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