Chinese Journal of Organic Chemistry >
Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds
Received date: 2022-04-25
Revised date: 2022-06-24
Online published: 2022-07-14
Supported by
Nanjing Tech University(39837146); Nanjing Tech University(39837118); National Natural Science Foundation of China(22001121); National Natural Science Foundation of Jiangsu Province(BK20180690)
Organofluorine compounds have been widely applied in various fields ranging from drug discovery, clinical medicines, agrochemistry, and materials science to organic synthesis, due to their special chemical and physical properties when compared with nonfluorinated analogs. In the past decades, significant progress has been made in the development of selective fluorination and fluoroalkylation for the synthesis of structurally diverse fluorine-containing molecules. Among them, the α-fluoroalkylated carbonyl group represents an important class of scaffold components in biologically active and druglike compounds. In this context, based on the use of difluorinated silyl enol ether (DFSEE) as a unique fluoroaklylating reagent, a variety of methods for the incorporation of gem-difluoroalkylated carbonyl moiety have been achieved, including aldol, Mannich, arylation, allylation, protonation, halogenation, conjugate addition, and olefination reactions. On the other hand, DFSEEs could also merge with new types of reactions such as radical-type difluoroalkylation and cascade reaction by virtue of their incredible reactive flexibility. In addition, the O-site selective addition of DFSEEs was also reported, enabling the construction of versatile gem-difluoroalkenes. Given the importance of organofluorine compounds and the synthetic potential of these avenues, herein, we highlight the recent advances in the functionalization of gem-difluorinated silyl enol ethers, which serve as key fluorine-containing building blocks for the synthesis of organofluorine compounds.
Mengmeng Guo , Zilun Yu , Yulan Chen , Danhua Ge , Mengtao Ma , Zhiliang Shen , Xueqiang Chu . Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3562 -3587 . DOI: 10.6023/cjoc202204060
| [1] | (a) Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432. |
| [1] | (b) Prchalová, E.; ?těpánek, O.; Smr?ek, S.; Kotora, M. Future Med. Chem. 2014, 6, 1201. |
| [2] | Hu, J.; Ding, K. Acta Chim. Sinica 2018, 76, 905. (in Chinese) |
| [2] | ( 胡金波, 丁奎岭, 化学学报 2018, 76, 905.) |
| [3] | (a) Ge, D.; Chu, X.-Q. Org. Chem. Front. 2022, 9, 2013. |
| [3] | (b) Chen, B.; Vicic, D. A. Top. Organomet. Chem. 2014, 52, 113. |
| [4] | (a) Schirlin, D.; Tarnus, C.; Baltzer, S.; Remy, J. M. Bioorg. Med. Chem. Lett. 1992, 2, 651. |
| [4] | (b) Dreyer, G. B.; Metcalf, B. W. Tetrahedron Lett. 1988, 29, 6885. |
| [4] | (c) Nikolaou, A.; Kokotou, M. G.; Vasilakaki, S.; Kokotos, G. Biochim. Biophys. Acta, Mol. Cell Biol. Lipids 2019, 1864, 941. |
| [4] | (d) Cregge, R. J.; Durham, S. L.; Farr, R. A.; Gallion, S. L.; Hare, C. M.; Hoffman, R. V.; Janusz, M. J.; Kim, H.-O.; Koehl, J. R.; Mehdi, S.; Metz, W. A.; Peet, N. P.; Pelton, J. T.; Schreuder, H. A.; Sunder, S.; Tardif, C. J. Med. Chem. 1998, 41, 2461. |
| [4] | (e) Silva, A. M.; Cachau, R. E.; Sham, H. L.; Erickson, J. W. J. Mol. Biol. 1996, 255, 321. |
| [4] | (f) Fah, C.; Hardegger, L. A.; Baitsch, L.; Schweizer, W. B.; Meyer, S.; Bur, D.; Diederich, F. Org. Biomol. Chem. 2009, 7, 3947. |
| [5] | (a) Mei, H.; Liu, J.; Fustero, S.; Román, R.; Ruzziconi, R.; Soloshonok, V. A.; Han, J. Org. Biomol. Chem. 2019, 17, 762. |
| [5] | (b) Gong, Y.; Yu, J.-S.; Hao, Y.-J.; Zhou, Y.; Zhou, J. Asian J. Org. Chem. 2019, 8, 610. |
| [5] | (c) Dong, D.-Q.; Yang, H.; Shi, J.-L.; Si, W.-J.; Wang, Z.-L.; Xu, X.-M. Org. Chem. Front. 2020, 7, 2538. |
| [5] | (d) Belhomme, M.-C.; Besset, T.; Poisson, T.; Pannecoucke, X. Chem. Eur. J. 2015, 21, 12836. |
| [5] | (e) Rong, J.; Ni, C.; Hu, J. Asian J. Org. Chem. 2017, 6, 139. |
| [6] | Yamana, M.; Ishihara, T.; Ando, T. Tetrahedron Lett. 1983, 24, 507. |
| [7] | (a) Liu, Y.-L.; Zhou, J. Chem. Commun. 2012, 48, 1919. |
| [7] | (b) Liu, Y.-L.; Zeng, X.-P.; Zhou, J. Acta Chim. Sinica 2012, 70, 1451 (in Chinese) |
| [7] | ( 刘运林, 周剑, 化学学报 2012, 70, 1451.) |
| [7] | (c) Liu, Y.-L.; Liao, F.-M.; Niu, Y.-F.; Zhao, X.-L.; Zhou, J. Org. Chem. Front. 2014, 1, 742. |
| [7] | (d) Liao, F.-M.; Liu, Y.-L.; Yu, J.-S.; Zhou, F.; Zhou, J. Org. Biomol. Chem. 2015, 13, 8906. |
| [7] | (e) Liao, F.-M.; Gao, X.-T.; Hu, X.-S.; Xie, S.-L.; Zhou, J. Sci. Bull. 2017, 62, 1504. |
| [8] | (a) Yu, J.-S.; Zhou, J. Org. Biomol. Chem. 2015, 13, 10968. |
| [8] | (b) Yu, J.-S.; Zhou, J. Org. Chem. Front. 2016, 3, 298. |
| [8] | (c) Hu, X.-S.; Du, Y.; Yu, J.-S.; Liao, F.-M.; Ding, P.-G.; Zhou, J. Synlett 2017, 28, 2194. |
| [8] | (d) Hu, X.-S.; Yu, J.-S.; Gong, Y.; Zhou, J. J. Fluorine Chem. 2019, 219, 106. |
| [9] | (a) Uneyama, K.; Tanaka, H.; Kobayashi, S.; Shioyama, M.; Amii, H. Org. Lett. 2004, 6, 2733. |
| [9] | (b) Guo, Y.; Shreeve, J. M. Chem. Commun. 2007, 3583. |
| [9] | (c) Guo, Y.; Twamley, B.; Shreeve, J. M. Org. Biomol. Chem. 2009, 7, 1716. |
| [9] | (d) Guo, Y.; Tao, G.-H.; Blumenfeld, A.; Shreeve, J. M. Organometallics 2010, 29, 1818. |
| [10] | (a) Lefebvre, O.; Brigaud, T.; Portella, C. J. Org. Chem. 2001, 66, 4348. |
| [10] | (b) Belanger, E.; Cantin, K.; Messe, O.; Tremblay, M.; Paquin, J.-F. J. Am. Chem. Soc. 2007, 129, 1034. |
| [11] | (a) Poisson, T.; Gembus, V.; Dalla, V.; Oudeyer, S.; Levacher, V. J. Org. Chem. 2010, 75, 7704. |
| [11] | (b) Liao, K.; Hu, X.-S.; Zhu, R.-Y.; Rao, R.-H.; Yu, J.-S.; Zhou, F.; Zhou, J. Chin. J. Chem. 2019, 37, 799. |
| [12] | Higashiya, S.; Chung, W. J.; Lim, D. S.; Ngo, S. C.; Kelly IV, W. H.; Toscano, P. J.; Welch, J. T. J. Org. Chem. 2004, 69, 6323. |
| [13] | (a) Yu, J.-S.; Liao, F.-M.; Gao, W.-M.; Liao, K.; Zuo, R.-L.; Zhou, J. Angew. Chem., Int. Ed. 2015, 54, 7381. |
| [13] | (b) Hao, Y.-J.; Hu, X.-S.; Yu, J.-S.; Zhou, F.; Zhou, Y.; Zhou, J. Tetrahedron 2018, 74, 7395. |
| [14] | (a) Liao, F.-M.; Cao, Z.-Y.; Yu, J.-S.; Zhou, J. Angew. Chem., Int. Ed. 2017, 56, 2459. |
| [14] | (b) Liao, F.-M.; Du, Y.; Zhou, F.; Zhou, J. Acta Chim. Sinica 2018, 76, 862. (in Chinese) |
| [14] | ( 廖富民, 杜溢, 周锋, 周剑, 化学学报 2018, 76, 862.) |
| [15] | Hu, X.-S.; Yu, J.-S.; Zhou, J. Chem. Commun. 2019, 55, 13638. |
| [16] | Chu, X.-Q.; Ge, D.; Cui, Y.-Y.; Shen, Z.-L.; Li, C.-J. Chem. Rev. 2021, 121, 12548. |
| [17] | Yu, J.; Liu, Y.; Tang, J.; Wang X.; Zhou, J. Angew. Chem., Int. Ed. 2014, 53, 9512. |
| [18] | (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. |
| [18] | (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. |
| [18] | (c) O’Hagan, D. Chem. Soc. Rev. 2008, 37, 308. |
| [19] | Tian, Y.-P.; Gong, Y.; Hu, X.-S.; Yu, J.-S.; Zhou, Y.; Zhou, J. Org. Biomol. Chem. 2019, 17, 9430. |
| [20] | Yang, J.; Liu, S.; Hong, P.; Li, J.; Wang, Z.; Ren, J. J. Org. Chem. 2022, 87, 1144. |
| [21] | (a) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. |
| [21] | (b) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. Synthesis 2013, 45, 1. |
| [22] | Liu, S.; Li, Y.; Wang, F.; Ma, C.; Yang, G.; Yang, J.; Ren, J. Synthesis 2022, 54, 161. |
| [23] | (a) Jonet, S.; Cherouvrier, F.; Brigaud, T.; Portella, C. Eur. J. Org. Chem. 2005, 4304. |
| [23] | (b) Yuan, Z.; Wei, Y.; Shi, M. Chin. J. Chem. 2010, 28, 1709. |
| [23] | (c) Chu, L.; Zhang, X.; Qing, F.-L. Org. Lett. 2009, 11, 2197. |
| [23] | (d) Wu, Y.-B.; Wan, L.; Lu, G.-P.; Cai, C. Eur. J. Org. Chem. 2017, 3438. |
| [24] | Hu, X.-S.; Ding, P.-G.; Yu, J.-S.; Zhou, J. Org. Chem. Front. 2019, 6, 2500. |
| [25] | (a) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328. |
| [25] | (b) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299. |
| [26] | Huang, X.; Zhang, Y.; Zhang, C.; Zhang, L.; Xu, Y.; Kong, L.; Wang, Z.-X.; Peng, B. Angew. Chem., Int. Ed. 2019, 58, 5956. |
| [27] | (a) Roche, S. P.; Porco Jr, J. A. Angew. Chem., Int. Ed. 2011, 50, 4068. |
| [27] | (b) Zheng, C.; You, S.-L. Nat. Prod. Rep. 2019, 36, 1589. |
| [27] | (c) Ding, Q.; Ye, Y.; Fan, R. Synthesis 2013, 45, 1. |
| [28] | Huang, X.; Zhang, Y.; Liang, W.; Zhang, Q.; Zhan, Y.; Kong, L.; Peng, B. Chem. Sci. 2020, 11, 3048. |
| [29] | (a) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832. |
| [29] | (b) Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200. |
| [30] | Huang, X.; Zhao, W.; Liang, Y.; Wang, M.; Zhan, Y.; Zhang, Y.; Kong, L.; Wang, Z.-X.; Peng, B. Org. Chem. Front. 2021, 8, 1280. |
| [31] | Gao, X.; Cheng, R.; Xiao, Y.-L.; Wan, X.-L.; Zhang, X. Chem 2019, 5, 2987. |
| [32] | Jiang, X.; Meyer, D.; Baran, D.; Cortes Gonzalez, M. A.; Szabo, K. J. J. Org. Chem. 2020, 85, 8311. |
| [33] | (a) Speck, K.; Magauer, T. J. Org. Chem. 2013, 9, 2048. |
| [33] | (b) Bhatia, R. K. Curr. Top. Med. Chem. 2016, 17, 189. |
| [34] | Rong, M.-Y.; Li, J.-S.; Zhou, Y.; Zhang, F.-G.; Ma, J.-A. Org. Lett. 2020, 22, 9010. |
| [35] | Hao, Y.-J.; Gong, Y.; Zhou, Y.; Zhou, J.; Yu, J.-S. Org. Lett. 2020, 22, 8516. |
| [36] | (a) Wencel-Delord, J.; Colobert, F. Org. Chem. Front. 2016, 3, 394. |
| [36] | (b) Colomer, I.; Chamberlain, A. E. R.; Haughey, M. B.; Donohoe, T. J. Nat. Rev. Chem. 2017, 1, 0088. |
| [37] | Li, J.; Xi, W.; Zhong, R.; Yang, J.; Wang, L.; Ding, H.; Wang, Z. Chem. Commun. 2021, 57, 1050. |
| [38] | (a) Zhang, K. F.; Bian, K. J.; Li, C.; Sheng, J.; Li, Y.; Wang, X. S. Angew. Chem., Int. Ed. 2019, 58, 5069. |
| [38] | (b) Taj Muhammad, M.; Jiao, Y.; Ye, C.; Chiou, M.-F.; Israr, M.; Zhu, X.; Li, Y.; Wen, Z.; Studer, A.; Bao, H. Nat. Commun. 2020, 11, 416. |
| [39] | Li, J.; Xi, W.; Liu, S.; Ruan, C.; Zheng, X.; Yang, J.; Wang, L.; Wang, Z. Org. Lett. 2021, 23, 7264. |
| [40] | (a) Hu, X.-S.; He, J.-X.; Dong, S.-Z.; Zhao, Q.-H.; Yu, J.-S.; Zhou, J. Nat. Commun. 2020, 11, 5500. |
| [40] | (b) Chen, G.; Liu, Y. Chin. J. Org. Chem. 2021, 41, 869. (in Chinese) |
| [40] | ( 陈国术, 刘运林, 有机化学 2021, 41, 869.) |
| [41] | Li, J.; Liu, S.; Zhong, R.; Yang, Y.; He, Y.; Yang, J.; Ma, Y.; Wang, Z. Org. Lett. 2021, 23, 5859. |
| [42] | (a) Hari, D. P.; Schroll, P.; Konig, B. J. Am. Chem. Soc. 2012, 134, 2958. |
| [42] | (b) Bu, M. J.; Niu, T. F.; Cai, C. Catal. Sci. Technol. 2015, 5, 830. |
| [43] | Wu, Y.-B.; Lu, G.-P.; Zhou, B.-J.; Bu, M.-J.; Wan, L.; Cai, C. Chem. Commun. 2016, 52, 5965. |
| [44] | Klauck, F. J. R.; James, M. J.; Glorius, F. Angew. Chem., Int. Ed. 2017, 56, 12336. |
| [45] | (a) Huang, Y.; Jia, J.; Huang, Q.-P.; Zhao, L.; Wang, P.; Gu, J.; He, C.-Y. Chem. Commun. 2020, 56, 14247. |
| [45] | (b) Huang, Q.-P.; Huang, Y.; Wang, A.-J.; Zhao, L.; Jia, J.; Yu, Y.; Tong, J.; Gu, J.; He, C.-Y. Org. Chem. Front. 2021, 8, 4438. |
| [46] | He, F.-S.; Yao, Y.; Xie, W.; Wu, J. Chem. Commun. 2020, 56, 9469. |
| [47] | Song, H.; Cheng, R.; Min, Q.-Q.; Zhang, X. Org. Lett. 2020, 22, 7747. |
| [48] | Zhu, X.; Huang, Y.; Xu, X.; Qing, F. Chin. Chem. Lett. 2022, 33, 817. |
| [49] | (a) Borth, P. W.; J. Econ. Entomol. 1986, 79, 1632. |
| [49] | (b) Medebielle, M.; Ait-Mohand, S.; Burkhloder, C.; Dolbier, W. R.; Laumond, G.; Aubertin, A. M. J. Fluorine Chem. 2005, 126, 533. |
| [50] | (a) Zou, J.-Y.; Wang, Y.-Z.; Sun, W.-H.; Lin, W.-J.; Liu, X.-Y. Org. Biomol. Chem. 2021, 19, 8696. |
| [50] | (b) Huang, Q.-P.; Li, W.-P.; Li, R.; Zhao, L.; Wang, H.-Y.; Li, X.; Wang, P.; He, C.-Y. Tetrahedron Lett. 2022, 97, 153782. |
| [51] | Shi, Y.; Pan, B.-W.; He, J.-X.; Zhou, Y.; Zhou, J.; Yu, J.-S. J. Org. Chem. 2021, 86, 7797. |
| [52] | ((a) Orsi, D. L.; Altman, R. A. Chem. Commun. 2017, 53, 7168. |
| [53] | ((a) Hao, Y.-J..; Yu, J.-S..; Zhou, Y..; Wang, X..; Zhou, J.. Acta Chim. Sinica 2018, 76, 925. (in Chinese) |
| [53] | ( 郝永佳, 余金生, 周英, 王欣, 周剑, 化学学报 2018, 76, 925.) |
| [54] | He, J.-X.; Zhang, Z.-H.; Mu, B.-S.; Cui, X.-Y.; Zhou, J.; Yu, J.-S. J. Org. Chem. 2021, 86, 9206. |
| [55] | Li, J.; Liu, S.; Zhong, R.; Yang, Y.; Xu, J.; Yang, J.; Ding, H.; Wang, Z. Org. Lett. 2021, 23, 9526. |
| [56] | Li, J.; Xi, W.; Liu, S.; Yang, Y.; Yang, J.; Ding, H.; Wang, Z. Chin. Chem. Lett. 2022, 3007. |
| [57] | Rios, R. Chem. Soc. Rev. 2012, 41, 1060. |
| [58] | Wu, H.; Hong, P.; Xi, W.; Li, J. Org. Lett. 2022, 24, 2488. |
/
| 〈 |
|
〉 |
