Chinese Journal of Organic Chemistry >
Recent Advances in the Decarboxylative Fluoroalkylation of Fluoroalkyl Carboxylic Acids
Received date: 2022-08-15
Revised date: 2022-09-26
Online published: 2022-10-25
Supported by
Natural Science Foundation of the Jiangsu Higher Education Institutions of China(22KJB150051); Natural Science Foundation of the Jiangsu Higher Education Institutions of China(19KJB150020)
Decarboxylation of fluoroalkyl carboxylic acid derivatives is an effective way to obtain fluoroalkyl radicals, which subsequently participates in the tandem and addition reactions of olefins, isonitriles and aromatic (hetero) rings, providing an important method to obtain divegent fluorine-containing molecules. A variety of fluoroalkyl cyclic compounds such as phenanthridines, dihydroflavonoid, quinolinones and indolones could be constructed using the tandem reaction initiated by fluoroalkyl radicals generated from fluoroalkyl carboxylic acids. The research progress of radical reactions induced by decarboxylation of fluoroalkyl carboxylic acids in recent years is summarized, which includes reaction design, reaction mechanism and outlook.
Key words： fluoroalkylation; decarboxylative reaction; carboxylic acid
Yuxi Zhu , Ting Xiao , Dong Xia , Wenchao Yang . Recent Advances in the Decarboxylative Fluoroalkylation of Fluoroalkyl Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4067 -4077 . DOI: 10.6023/cjoc202208017
| [1] | (a) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513. |
| [1] | (b) Ni, C.; Hu, J. Chem. Soc. Rev. 2016, 45, 5441. |
| [1] | (c) Zhang, X.; Tang, P. Sci. China: Chem. 2019, 62, 525. |
| [1] | (d) Feng, Z.; Xiao, Y.-L.; Zhang, X. Acc. Chem. Res. 2018, 51, 2264. |
| [1] | (e) Zhang, C.-P.; Chen, Q.-Y.; Guo, Y.; Xiao, J.-C.; Gu, Y.-C. Chem. Soc. Rev. 2012, 41, 4536. |
| [2] | (a) Dong, D.-Q.; Yang, H.; Shi, J.-L.; Si, W.-J.; Wang, Z.-L.; Xu, X.-M. Org. Chem. Front. 2020, 7, 2538. |
| [2] | (b) Shao, X.; Xu, C.; Lu, L.; Shen, Q. Acc. Chem. Res. 2015, 48, 1227. |
| [2] | (c) Wang, Z.; Sun, Y.; Shen, L.-Y.; Yang, W.; Meng, F.; Li, P. Org. Chem. Front. 2022, 9, 853. |
| [2] | (d) Wang, J.; Liu, H. Chin. J. Org. Chem. 2011, 31, 1785. (in Chinese) |
| [2] | ( 王江, 柳红, 有机化学, 2011, 31, 1785.) |
| [2] | (e) Zhang, J.; Jin, C.; Zhang, Y. Chin. J. Org. Chem. 2014, 34, 662. (in Chinese) |
| [2] | ( 张霁, 金传飞, 张英俊, 有机化学, 2014, 34, 662.) |
| [3] | (a) Aguilar Troyano, F. J.; Merkens, K.; Anwar, K.; Gomez-Suarez, A. Angew. Chem., Int. Ed. 2021, 60, 1098. |
| [3] | (b) Shi, Y.; Xiao, H.; Xu, X.-H.; Huang, Y. Org. Biomol. Chem. 2018, 16, 8472. |
| [3] | (c) Xiang, J.; Shang, M.; Kawamata, Y.; Lundberg, H.; Reisberg, S. H.; Chen, M.; Mykhailiuk, P.; Beutner, G.; Collins, M. R.; Davies, A.; Del Bel, M.; Gallego, G. M.; Spangler, J. E.; Starr, J.; Yang, S.; Blackmond, D. G.; Baran, P. S. Nature 2019, 573, 398. |
| [3] | (d) Brigham, C. E.; Malapit, C. A.; Lalloo, N.; Sanford, M. S. ACS Catal. 2020, 10, 8315. |
| [3] | (e) Mei, W.; Kong, Y.; Yan, G. Org. Chem. Front. 2021, 8, 5516. |
| [4] | (a) Yang, W.-C.; Feng, J.-G.; Wu, L.; Zhang, Y.-Q. Adv. Synth. Catal. 2019, 361, 1700. |
| [4] | (b) Si, Y.-F.; Lv, Q.-Y.; Yu, B. Adv. Synth. Catal. 2021, 363, 4640. |
| [4] | (c) Lv, Y.; Cui, H.; Meng, N.; Yue, H.; Wei, W. Chin. Chem. Lett. 2022, 33, 97. |
| [4] | (d) Yang, W.-C.; Zhang, M.-M.; Feng, J.-G. Adv. Synth. Catal. 2020, 362, 4446. |
| [4] | (e) Shang, T.; Lu, L.; Cao, Z.; Liu, Y.; He, W.; Yu, B. Chem. Commun. 2019, 55, 5408. |
| [5] | Wan, W.; Ma, G.; Li, J.; Chen, Y.; Hu, Q.; Li, M.; Jiang, H.; Deng, H.; Hao, J. Chem. Commun. 2016, 52, 1598. |
| [6] | (a) Wan, W.; Li, J.; Ma, G.; Chen, Y.; Jiang, H.; Deng, H.; Hao, J. Org. Biomol. Chem. 2017, 15, 5308. |
| [6] | (b) Li, Y.-L.; Wang, J.-B.; Wang, X.-L.; Cao, Y.; Deng, J. Eur. J. Org. Chem. 2017, 2017, 6052. |
| [7] | Huang, C.-M.; Li, J.; Wang, S.-H.; Ai, J.-J.; Liu, X.-Y.; Rao, W.-D.; Wang, S.-Y. J. Org. Chem. 2021, 86, 8437. |
| [8] | Zhao, F.; Guo, S.; Zhang, Y.; Sun, T.; Yang, B.; Ye, Y.; Sun, K. Org. Chem. Front. 2021, 8, 6895. |
| [9] | Zhou, Y.; Xiong, Z.; Qiu, J.; Kong, L.; Zhu, G. Org. Chem. Front. 2019, 6, 1022. |
| [10] | Cui, Q.; Teng, F.; Yang, H.; Xun, C.; Huang, W.; Lu, Z.; Zhu, M.; Ouyang, W.; He, W.-M. Chem.-Asian J. 2022, 17, e202101139. |
| [11] | Barata-Vallejo, S.; Postigo, A. Chem.-Eur. J. 2020, 26, 11065. |
| [12] | Shi, G.; Shao, C.; Pan, S.; Yu, J.; Zhang, Y. Org. Lett. 2015, 17, 38. |
| [13] | Proctor, R. S. J.; Phipps, R. J. Angew. Chem., Int. Ed. 2019, 58, 13666. |
| [14] | Truong, T. T.; Christensen, S. B.; Nielsen, J. Chem.-Eur. J. 2017, 23, 18125. |
| [15] | Guo, C.; Liu, Z.; Li, X.; Han, X.; Li, Y.; Liu, H.; Zhang, L.; Li, X.; Dong, Y. Chem. Commun. 2022, 58, 1147. |
| [16] | Guo, C.; Han, X.; Li, X.; Diao, Z.; Li, X.; Dong, Y. Asian J. Org. Chem. 2022, 11, e202100663. |
| [17] | Galal, S. A.; Khairat, S. H. M.; Ragab, F. A. F.; Abdelsamie, A. S.; Ali, M. M.; Soliman, S. M.; Mortier, J.; Wolber, G.; El Diwani, H. I. Eur. J. Med. Chem. 2014, 86, 122. |
| [18] | Sun, K.; Xiao, F.; Yu, B.; He, W.-M. Chin. J. Catal. 2021, 42, 1921. |
| [19] | Hong, G.; Yuan, J.; Fu, J.; Pan, G.; Wang, Z.; Yang, L.; Xiao, Y.; Mao, P.; Zhang, X. Org. Chem. Front. 2019, 6, 1173. |
| [20] | Gao, Y.; Zhao, L.; Xiang, T.; Li, P.; Wang, L. RSC Adv. 2020, 10, 10559. |
| [21] | Xie, X.; Zhang, Y.; Hao, J.; Wan, W. Org. Biomol. Chem. 2020, 18, 400. |
| [22] | Gao, Y.; Li, L.; Liu, J.; Wang, L.; Wang, M. Synthesis 2021, 53, 1636. |
| [23] | (a) Yu, D.; Suzuki, M.; Xie, L.; Morris-Natschke, S. L.; Lee, K.-H. Med. Res. Rev. 2003, 23, 322. |
| [23] | (b) Bras, G. L.; Radanyi, C.; Peyrat, J.-F.; Brion, J.-D.; Alami, M.; Marsaud, V.; Stella, B.; Renoir, J.-M. J. Med. Chem. 2007, 50, 6189. |
| [23] | (c) Hassan, M. Z.; Osman, H.; Ali, M. A.; Ahsan, M. J. Eur. J. Med. Chem. 2016, 123, 236. |
| [23] | (d) Anamika, D.; Utreja, D.; Ekta; Jain, N.; Sharma, S. Curr. Org. Chem. 2019, 22, 2509. |
| [23] | (e) Yang, W.; Yang, S.; Li, P.; Wang, L. Chem. Commun. 2015, 51, 7520. |
| [24] | (a) Chen, Z.; Bai, X.; Sun, J.; Xu, Y. J. Org. Chem. 2020, 85, 7674. |
| [24] | (b) Chen, Z.; Sun, J.; Ke, Z.; Huang, X.; Li, Z. Org. Chem. Front. 2022, 9, 757. |
| [25] | Zhao, H.-X.; Ma, G.-B.; Xie, X.-Y.; Wang, Y.; Hao, J.; Wan, W. Chem. Commun. 2019, 55, 3927. |
| [26] | (a) Mizuta, S.; Stenhagen, I. S. R.; O’Duill, M.; Wolstenhulme, J.; Kirjavainen, A. K.; Forsback, S. J.; Tredwell, M.; Sandford, G.; Moore, P. R.; Huiban, M.; Luthra, S. K.; Passchier, J.; Solin, O.; Gouverneur, V. Org. Lett. 2013, 15, 2648. |
| [26] | (b) Zhou, M.; Ni, C.; He, Z.; Hu, J. Org. Lett. 2016, 18, 3754. |
| [26] | (c) Zhang, Q.-W.; Brusoe, A. T.; Mascitti, V.; Hesp, K. D.; Blakemore, D. C.; Kohrt, J. T.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 9758. |
| [27] | (a) Chen, F.; Hashmi, A. S. K. Org. Lett. 2016, 18, 2880. |
| [27] | (b) Li, X.; Li, S.; Sun, S.; Yang, F.; Zhu, W.; Zhu, Y.; Wu, Y.; Wu, Y. Adv. Synth. Catal. 2016, 358, 1699. |
| [28] | (a) Wang, Y.; Zhao, H.; Xie, X.; Jiang, H.; Deng, H.; Hao, J.; Wan, W. Synth. Commun. 2019, 49, 2961. |
| [28] | (b) Zhang, Y.; Wang, Q.; Peng, Y.; Gong, H.; Chen, H.; Deng, H.; Hao, J.; Wan, W. Org. Biomol. Chem. 2021, 19, 7024. |
| [29] | Debien, L.; Quiclet-Sire, B.; Zard, S. Z. Acc. Chem. Res. 2015, 48, 1237. |
| [30] | Li, X.; Zhang, R. H.; Zhang, X. F.; Zhu, P. Y.; Yao, T. L. Chem.-Asian J. 2020, 15, 1175. |
| [31] | (a) Yang, B.; Xu, X.-H.; Qing, F.-L. Org. Lett. 2016, 18, 5956. |
| [31] | (b) Guo, C.; Han, X.; Feng, Y.; Liu, Z.; Li, Y.; Liu, H.; Zhang, L.; Dong, Y.; Li, X. J. Org. Chem. 2022, 87, 9232. |
/
| 〈 |
|
〉 |
