Chinese Journal of Organic Chemistry >
Advances in the Synthesis of Mono/Di/Polyfluoroalkyl Ethers
Received date: 2024-01-05
Revised date: 2024-03-05
Online published: 2024-03-20
Supported by
Harbin University of Commerce Teachers’ “Innovation” Project in 2021(LH2020H068); Innovative Talent Project of Ministry of Education of Heilongjiang Province(UNPYSCT-2018139); Scientific Research Project on Traditional Chinese Medicine in Heilongjiang Province(ZYW2023-075); Basic Scientific Research Funds for Provincial Higher Education Institutions in Heilongjiang Province in 2023(2023-KYYWF-1041)
Fluoroalkyl ethers are widely used in organic chemistry, materials science, environmental science, life science and other fields, especially in biopharmaceuticals, where the introduction of fluoroalkoxy groups has attracted much attention for their ability to improve metabolic stability and cell membrane permeability, thus significantly improving the pharmacodynamic and pharmacokinetic properties of biologically active molecules. Although several strategies for the construction of fluoroalkyl ethers have been reported, the number of fluoroalkyl ether-containing drugs and agrochemicals on the market is still small. Therefore, the development of effective methods for the preparation of fluoroalkyl ethers is a much needed and challenging task. The progress of research on the synthesis of monofluoromethyl ethers, difluoromethyl ethers, and polyfluoroalkyl ethers is categorized and summarized, mainly in terms of C—O bond-coupled indirect fluoroalkoxylation, C(sp2)—H, C(sp2)—C, C(sp3)—X (heteroatom) direct fluoroalkoxylation and other direct fluoroalkoxylation. The possible mechanisms and applicability of some reactions are also discussed.
Dongxue Song , Hongqiong Zhao , Ying Xu , Chenfeng Ji , Yingjie Liu . Advances in the Synthesis of Mono/Di/Polyfluoroalkyl Ethers[J]. Chinese Journal of Organic Chemistry, 2024 , 44(7) : 2174 -2203 . DOI: 10.6023/cjoc202401003
| [1] | Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. |
| [2] | Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev. 2011, 40, 3496. |
| [3] | Huchet, Q. A.; Trapp, N.; Kuhn, B.; Wagner, B.; Fischer, H.; Kratochwil, N. A.; Carreira, E. M.; Müller, K. J. Fluorine Chem. 2017, 198, 34. |
| [4] | Federsela, D.; Herrmanna, A.; Christena, D.; Sanderb., S.; Willnerb, H.; Oberhammer, H. J. Mol. Struct. 2001, 567, 127. |
| [5] | Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827. |
| [6] | Leroux, F. R.; Manteau, B.; Vors, J.-P.; Pazenok, S. Beilstein J. Org. Chem. 2008, 4, 13. |
| [7] | Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. |
| [8] | Xing, L.; Blakemore, D. C.; Narayanan, A.; Unwalla, R.; Lovering, F.; Denny, R. A.; Zhou, H.; Bunnage, M. E. ChemMedChem 2015, 10, 715. |
| [9] | Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207. |
| [10] | Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165. |
| [11] | Yang, Q.; Njardarson, J. T. Tetrahedron Lett. 2013, 54, 7080. |
| [12] | Cheer, S. M.; Prakash, A.; Faulds, D.; Lamb, H. M. Drugs 2003, 63, 101. |
| [13] | Eignerova, B.; Sedlak, D.; Dracinsky, M.; Bartunek, P.; Kotora, M. J. Med. Chem. 2010, 53, 6947. |
| [14] | Duan, J. J.; Lu, Z.; Jiang, B.; Stachura, S.; Weigelt, C. A.; Sack, J. S.; Khan, J.; Ruzanov, M.; Galella, M. A.; Wu, D. R.; Yarde, M.; Shen, D. R.; Shuster, D. J.; Borowski, V.; Xie, J. H.; Zhang, L.; Vanteru, S.; Gupta, A. K.; Mathur, A.; Zhao, Q.; Foster, W.; Salter-Cid, L. M.; Carter, P. H.; Dhar, T. G. M. ACS Med. Chem. Lett. 2019, 10, 367. |
| [15] | Cherney, R. J.; Cornelius, L. A. M.; Srivastava, A.; Weigelt, C. A.; Marcoux, D.; Duan, J. J.; Shi, Q.; Batt, D. G.; Liu, Q.; Yip, S.; Wu, D. R.; Ruzanov, M.; Sack, J.; Khan, J.; Wang, J.; Yarde, M.; Cvijic, M. E.; Mathur, A.; Li, S.; Shuster, D.; Khandelwal, P.; Borowski, V.; Xie, J.; Obermeier, M.; Fura, A.; Stefanski, K.; Cornelius, G.; Tino, J. A.; Macor, J. E.; Salter-Cid, L.; Denton, R.; Zhao, Q.; Carter, P. H.; Dhar, T. G. M. ACS Med. Chem. Lett. 2020, 11, 1221. |
| [16] | Wang, J.; Sánchez-Roselló, M.; Ace?a, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2013, 114, 2432. |
| [17] | Aliot, E.; Capucci, A.; Crijns, H. J.; Goette, A.; Tamargo, J. Europace 2011, 13, 161. |
| [18] | Satoh, H. Curr. Pharm. Des. 2013, 19, 67. |
| [19] | Harikrishnan, L. S.; Finlay, H. J.; Qiao, J. X.; Kamau, M. G.; Jiang, J.; Wang, T. C.; Li, J.; Cooper, C. B.; Poss, M. A.; Adam, L. P.; Taylor, D. S.; Chen, A. Y. A.; Yin, X.; Sleph, P. G.; Yang, R. Z.; Sitkoff, D. F.; Galella, M. A.; Nirschl, D. S.; Van Kirk, K.; Miller, A.V.; Huang, C. S.; Chang, M.; Chen, X.-Q.; Salvati, M. E.; Wexler, R. R.; Lawrence, R. M. J. Med. Chem. 2012, 55, 6162. |
| [20] | Kotańska, M.; Lustyk, K.; Bucki, A.; Marcinkowska, M.; ?nieci- kowska, J.; Ko?aczkowski, M. Metab. Brain Dis. 2018, 33, 733. |
| [21] | Ogawa, Y.; Tokunaga, E.; Kobayashi, O.; Hirai, K.; Shibata, N. iScience 2020, 23, 101467. |
| [22] | Kawamura, K.; Tsukada, H.; Shiba, K.; Tsuji, C.; Harada, N.; Kimura, Y.; Ishiwata, K. Nucl. Med. Biol. 2007, 34, 571. |
| [23] | Donohue, S. R.; Krushinski, J. H.; Pike, V. W.; Chernet, E.; Phebus, L.; Chester-field, A. K.; Felder, C. C.; Halldin, C.; Schaus, J. M. J. Med. Chem. 2008, 51, 5833. |
| [24] | Hebeisen, P.; Weiss, U.; Alker, A.; Kuhn, B.; Müller, K.; Wang, F.; Prakash, G. K. S. Eur. J. Org. Chem. 2018, 2018, 3724. |
| [25] | Lee, K. N.; Lee, J. W.; Ngai, M. Y. Tetrahedron 2018, 74, 7127. |
| [26] | Si, Y. F.; Tang, P. P. Chin. J. Chem. 2023, 41, 2179. |
| [27] | Iwataa, R.; Pascalic, C.; Bognic, A.; Furumotob, S.; Terasakid, K.; Yanai, K. Appl. Radiat. Isot. 2002, 57, 347. |
| [28] | Zhang, W.; Zhu, L.; Hu, J. Tetrahedron 2007, 63, 10569. |
| [29] | Zhang, M.-R.; Ogawa, M.; Furutsuka, K.; Yoshida, Y.; Suzuki, K. J. Fluorine Chem. 2004, 125, 1879. |
| [30] | Prakash, G. K. S.; Ledneczki, I.; Chacko, S.; Olah, G. A. Org. Lett. 2008, 10, 557. |
| [31] | Melngaile, R.; Sperga, A.; Baldridge, K. K.; Veliks, J. Org. Lett. 2019, 21, 7174. |
| [32] | Veliks, J.; Kazia, A. Chem.-Eur. J. 2019, 25, 3786. |
| [33] | Kazia, A.; Melngaile, R.; Mishnev, A.; Veliks, J. Org. Biomol. Chem. 2020, 18, 1384. |
| [34] | Carbonnel, E.; Pannecoucke, X.; Besset, T.; Jubault, P.; Poisson, T. Chem. Commun. 2018, 54, 2491. |
| [35] | Nomura, Y.; Tokunaga, E.; Shibata, N. Angew. Chem., Int. Ed. 2011, 50, 1885. |
| [36] | Shen, X.; Zhou, M.; Ni, C.; Zhang, W.; Hu, J. Chem. Sci. 2014, 5, 117. |
| [37] | Zhang, W.; Wang, F.; Hu, J. Org. Lett. 2009, 11, 2109. |
| [38] | Johnson, C. R.; Katekar, G. F. J. Am. Chem. Soc. 1970, 92, 5753. |
| [39] | Liu, Y.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2017, 56, 9930. |
| [40] | Wang, L.; Wei, J.; Wu, R.; Cheng, G.; Li, X.; Hu, J.; Hu, Y.; Sheng, R. Org. Chem. Front. 2017, 4, 214. |
| [41] | Senatore, R.; Malik, M.; Spreitzer, M.; Holzer, W.; Pace, V. Org. Lett. 2020, 22, 1345. |
| [42] | Zhao, Q.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2017, 56, 11575. |
| [43] | Liu, F.; Jiang, L.; Qiu, H.; Yi, W. Org. Lett. 2018, 20, 6270. |
| [44] | Hong, X.; Liu, Y.; Lu, L.; Shen, Q. Chin. J. Chem. 2020, 38, 1317. |
| [45] | Hu, J.; Ni, C. Synthesis 2014, 46, 842. |
| [46] | Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2013, 52, 2092. |
| [47] | Levchenko, K.; Datsenko, O. P.; Serhiichuk, O.; Tolmachev, A.; Iaroshenko, V. O.; Mykhailiuk, P. K. J. Org. Chem. 2016, 81, 5803. |
| [48] | Yang, J.; Jiang, M.; Jin, Y.; Yang, H.; Fu, H. Org. Lett. 2017, 19, 2758. |
| [49] | Dolbier, W. R.; Wang, F.; Tang, X.; Thomoson, C. S.; Wang, L. J. Fluorine Chem. 2014, 160, 72. |
| [50] | Zhu, J. S.; Liu, Y. F.; Shen, Q. L. Angew. Chem., Int. Ed. 2016, 55, 9050. |
| [51] | Xie, Q. Q.; Ni, C. F.; Zhang, R. Y.; Li, L. C.; Rong, J.; Hu, J. B. Angew. Chem., Int. Ed. 2017, 56, 3206. |
| [52] | Liu, G.-K.; Li, X.; Qin, W.-B.; Peng, X.-S.; Wong, H. N. C.; Zhang, L.-X.; Zhang, X.-H. Chem. Commun. 2019, 55, 7446. |
| [53] | Hagooly, Y.; Cohen, O.; Rozen, S. Tetrahedron Lett. 2009, 50, 392. |
| [54] | Zhang, R. Y.; Li, Q. G.; Xie, Q. Q.; Ni, C. F.; Hu, J. B. Chem.-Eur. J. 2021, 27, 17773. |
| [55] | Zhu, X. J.; Wei, J.; Hu, C. X.; Xiao, Q. T.; Cai, L. T.; Wang, H.; Xie, Y. Y.; Sheng, R. Eur. J. Org. Chem. 2022, 2022, e202200629. |
| [56] | Newton, J. J.; Engüdar, G.; Brooke, A. J.; Nodwell, M. B.; Horngren‐Rhodes, H.; Martin, R. E.; Schaffer, P.; Britton, R.; Friesen, C. M. Chem.-Eur. J. 2023, 29, e202202862. |
| [57] | van Bonn, P.; Ke, J. B.; Weike, C.; Ward, J. S.; Rissanen, K.; Bolm, C. CCS Chem. 2023, 5, 1737. |
| [58] | Bodor, N.; Huang, M.-J.; Szántay Jr, C.; SzBntay, C. Tetrahedron 1992, 48, 5823. |
| [59] | Nakai, T.; Tanaka, K.; Ishikawa, N. J. Fluorine Chem. 1977, 9, 89. |
| [60] | Cushman, M.; He, H.-M.; Katzenellenbogen, J. A.; Varma, R. K.; Hamel, E.; Lin, C. M.; Ram, S.; Sachdeva, Y. P. J. Med. Chem. 1997, 40, 2323. |
| [61] | Michellys, P. Y.; Ardecky, R. J.; Chen, J. H.; D'Arrigo, J.; Grese, T. A.; Karanewsky, D. S.; Leibowitz, M. D.; Liu, S.; Mais, D. A.; Mapes, C. M.; Montrose-Rafizadeh, C.; Ogilvie, K. M.; Reifel- Miller, A.; Rungta, D.; Thompson, A. W.; Tyhonas, J. S.; Boehm, M. F. J. Med. Chem. 2003, 46, 4087. |
| [62] | Sheppard, W. A. J. Org. Chem. 1964, 29, 1. |
| [63] | Aldrich, P. E.; Sheppard, W. A. J. Org. Chem. 1964, 29, 11. |
| [64] | Lee, J. W.; Spiegowski, D. N.; Ngai, M. Y. Chem. Sci. 2017, 8, 6066. |
| [65] | Lee, K. N.; Lei, Z.; Morales-Rivera, C. A.; Liu, P.; Ngai, M. Y. Org. Biomol. Chem. 2016, 14, 5599. |
| [66] | Tabolin, A. A.; Ioffe, S. L. Chem. Rev. 2014, 114, 5426. |
| [67] | Bertoli, G.; Martínez, á. M.; Goebel, J. F.; Belmonte, D.; Sivendran, N.; Goo?en, L. J. Angew. Chem., Int. Ed. 2023, 62, e202215920. |
| [68] | Martínez, á. M.; Hayrapetyan, D.; van Lingen, T.; Dyga, M.; Goo?en, L. J. Nat. Commun. 2020, 11, 4407. |
| [69] | Zheng, W.; Lee, J. W.; Morales-Rivera, C. A.; Liu, P.; Ngai, M. Y. Angew. Chem., Int. Ed. 2018, 57, 13795. |
| [70] | Lee, J. W.; Zheng, W.; Morales-Rivera, C. A.; Liu, P.; Ngai, M. Y. Chem. Sci. 2019, 10, 3217. |
| [71] | Zheng, W.; Morales-Rivera, C. A.; Lee, J. W.; Liu, P.; Ngai, M. Y. Angew. Chem., Int. Ed. 2018, 57, 9645. |
| [72] | Simmons, E. M.; Hartwig, J. F. Angew. Chem. 2012, 124, 3120. |
| [73] | Cernak, T.; Dykstra, K. D.; Tyagarajan, S.; Vachal, P.; Krska, S. W. Chem. Soc. Rev. 2016, 45, 546. |
| [74] | Nagib, D. A.; MacMillan, D. W. Nature 2011, 480, 224. |
| [75] | Bock, C.; Meyer, T.; Whitten, D. J. Am. Chem. Soc. 1975, 97, 2909. |
| [76] | Juris, A.; Balzani, V.; Belser, P.; von Zelewsky, A. Helv. Chim. Acta 1981, 64, 2175. |
| [77] | Lee, J. W.; Lim, S.; Maienshein, D. N.; Liu, P.; Ngai, M. Y. Angew. Chem., Int. Ed. 2020, 59, 21475. |
| [78] | Sakuratani, K.; Togo, H. Synthesis 2003, 1, 21. |
| [79] | Novak, I.; Harrison, L. J.; Kova?, B.; Pratt, L. M. J. Org. Chem. 2004, 69, 7628. |
| [80] | Xu, T.; Cheung, C. W.; Hu, X. Angew. Chem., Int. Ed. 2014, 53, 4910. |
| [81] | Rong, J.; Deng, L.; Tan, P.; Ni, C.; Gu, Y.; Hu, J. Angew. Chem., Int. Ed. 2016, 55, 2743. |
| [82] | Lin, D.; Prakash, G. K. S. Org. Lett. 2022, 24, 7707. |
| [83] | Thomoson, C. S.; Dolbier Jr, W. R. J. Org. Chem. 2013, 78, 8904. |
| [84] | Rossler, S. L.; Jelier, B. J.; Magnier, E.; Dagousset, G.; Carreira, E. M.; Togni, A. Angew. Chem., Int. Ed. 2020, 59, 9264. |
| [85] | Xu, J.; Yang, H. Y.; Cai, H.; Bao, H. Y.; Li, W. M.; Zhang, P. F. Org. Lett. 2019, 21, 4698. |
| [86] | Xu, X. B.; Xia, C. C.; Li, X. J.; Sun, J.; Hao, L. Q. RSC Adv. 2020, 10, 2016. |
| [87] | You, G. R.; Yan, J. Z. ChemistrySelect 2021, 6, 13736. |
| [88] | Tong, C. L.; Xu, X. H.; Qing, F. L. Angew. Chem., Int. Ed. 2021, 60, 22915. |
| [89] | Jin, L.; Zhang, X. L.; Guo, R. L.; Wang, M. Y.; Gao, Y. R.; Wang, Y. Q. Org. Lett. 2021, 23, 1921. |
| [90] | Yang, L.; Li, S. D.; Cai, L.; Ding, Y. Z.; Fu, L.; Cai, Z. H.; Ji, H. F.; Li, G. Org. Lett. 2017, 19, 2746. |
| [91] | Liu, Y. B.; Ge, H. B. Nat. Chem. 2017, 9, 26. |
| [92] | Sathyamoorthi, S.; Banerjee, S. ChemistrySelect 2017, 2, 10678. |
| [93] | Chen, X. Y.; Ozturk, S.; Sorensen, E. J. Org. Lett. 2017, 19, 1140. |
| [94] | Zhou, J. Y.; Liu, D.; Bai, C. L. M.; Bao, A.; Muschin, T.; Baiyin, M.; Bao, Y. S. Org. Chem. Front. 2021, 8, 5975. |
| [95] | Shinde, V. N.; Rangan, K.; Kumar, D.; Kumar, A. J. Org. Chem. 2021, 86, 9755. |
| [96] | Jiang, Y. F.; Pan, C. H.; Tang, T.; Liu, M. R.; Zhang, X. X. Org. Biomol. Chem. 2023, 21, 2748. |
| [97] | Ramkumar, N.; Sperga, A.; Belyakov, S.; Mishnev, A.; Zacs, D.; Veliks, J. Adv. Synth. Catal. 2023, 365, 1. |
| [98] | Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40. 102. |
| [99] | Yasu, Y.; Koike, T.; Akita, M. Angew. Chem., Int. Ed. 2012, 51, 9567. |
| [100] | Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. |
| [101] | Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075. |
| [102] | Chen, C. H.; Luo, Y. X.; Fu, L.; Chen, P. H.; Lan, Y.; Liu, G. S. J. Am. Chem. Soc. 2018, 140, 1207. |
| [103] | Barthelemy, A. L.; Tuccio, B.; Magnier, E.; Dagousset, G. Angew. Chem., Int. Ed. 2018, 57, 13790. |
| [104] | Banoun, C.; Bourdreux, F.; Magnier, E.; Dagousset, G. Org. Lett. 2021, 23, 8926. |
| [105] | Liu, S.; Wang, S.; Wang, P.; Huang, Z.; Wang, T.; Lei, A. Nat. Commun. 2022, 13, 4430. |
| [106] | Hu, X.; Zhang, G. T.; Bu, F. X.; Nie, L.; Lei, A. W. ACS Catal. 2018, 8, 9370. |
| [107] | Liu, Y. C.; Shi, B. Y.; Liu, Z.; Gao, R. F.; Huang, C. L.; Alhumade, H.; Wang, S. C.; Qi, X. T.; Lei, A. W. J. Am. Chem. Soc. 2021, 143, 20863. |
| [108] | Peterman, K. E.; Dmowski, W. Org. Prep. Proced. Int. 1991, 23, 760. |
| [109] | Chambers, R. D.; Korn, S. R.; Sandford, G. J. Fluorine Chem. 1994, 69, 103. |
| [110] | Petrov, V. A. J. Org. Chem. 1995, 60, 3423. |
| [111] | Galimberti, M.; Fontana, G.; Resnati, G.; Navarrini, W. J. Fluorine Chem. 2005, 126, 1578. |
| [112] | Wang, Y. G.; You, Y.; Weng, Z. Q. J. Fluorine Chem. 2015, 175, 51. |
| [113] | Gupton, J. T.; Idoux, J. P.; Colon, C.; Rampi, R. Synth. Commun. 1982, 12, 695. |
| [114] | Idoux, J. P.; Gupton, J. T.; McCurry, C. K.; Crews, A. D.; Jurss, C. D.; Colon, C.; Rampi, R. C. J. Org. Chem. 1983, 48, 3771. |
| [115] | Idoux, J. P.; Madenwald, M. L.; Garcia, B. S.; Chu, D. L.; Gupton, J. T. J. Org. Chem. 1985, 50, 1876. |
| [116] | Barbas, R.; Botija, M.; Camps, H.; Portell, A.; Prohens, R.; Puigjaner, C. Org. Process Res. Dev. 2007, 11, 1131. |
| [117] | Burgos, C. H.; Barder, T. E.; Huang, X. H.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 4321. |
| [118] | Sang, R. C.; Korkis, S. E.; Su, W. Q.; Ye, F.; Engl, P. S.; Berger, F.; Ritter, T. Angew. Chem., Int. Ed. 2019, 58, 16161. |
| [119] | Menczinger, B.; Nemes, A.; Szabó, D.; Schlosser, G.; Jernei, T.; Csámpai, A.; Rábai, J. J. Fluorine Chem. 2020, 231, 109464. |
| [120] | Vuluga, D.; Legros, J.; Crousse, B.; Bonnet-Delpon, D. Eur. J. Org. Chem. 2009, 2009, 3513. |
| [121] | Huang, R. L.; Huang, Y. J.; Lin, X. X.; Rong, M. G.; Weng, Z. Q. Angew. Chem., Int. Ed. 2015, 54, 5736. |
| [122] | Wu, X. X.; Fors, B. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9943. |
| [123] | Zhang, H.; Ruiz-Castillo, P.; Buchwald, S. L. Org. Lett. 2018, 20, 1580. |
| [124] | Rangarajan, T. M.; Singh, R.; Brahma, R.; Devi, K.; Singh, R. P.; Singh, R. P.; Prasad, A. K. Chem.-Eur. J. 2014, 20, 14218. |
| [125] | Rangarajan, T. M.; Devi, K.; Ayushee; Prasad, A. K.; Singh, R. P. Tetrahedron 2015, 71, 8307. |
| [126] | Szpera, R.; Isenegger, P. G.; Ghosez, M.; Straathof, N. J. W.; Cookson, R.; Blakemore, D. C.; Richardson, P.; Gouverneur, V. Org. Lett. 2020, 22, 6573. |
| [127] | Terrett, J. A.; Cuthbertson, J. D.; Shurtleff, V. W.; MacMillan, D. W. C. Nature 2015, 524, 330. |
| [128] | Petho, B.; Zwillinger, M.; Csenki, J. T.; Káncz, A. E.; Krámos, B.; Müller, J.; Balogh, G. T.; Novák, Z. Chem.-Eur. J. 2017, 23, 15628. |
| [129] | Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381. |
| [130] | Wang, R. X.; Wang, L.; Zhang, K. N.; Li, J. Y.; Zou, D. P.; Wu, Y. J.; Wu, Y. S. Tetrahedron Lett. 2015, 56, 4815. |
| [131] | Zhang, K.; Xu, X. H.; Qing, F. L. J. Fluorine Chem. 2017, 196, 24. |
| [132] | Maiti, S.; Alam, T.; Mal, P. Asian J. Org. Chem. 2018, 7, 715. |
| [133] | Sato, T.; Nogi, K.; Yorimitsu, H. ChemCatChem 2020, 12, 3467. |
| [134] | Sokolenko, T. M.; Davydova, Y. A.; Yagupolskii, Y. L. J. Fluorine Chem. 2012, 136, 20. |
| [135] | Zhou, M.; Ni, C. F.; Zeng, Y. W.; Hu, J. B. J. Am. Chem. Soc. 2018, 140, 6801. |
| [136] | Luo, Y.; Hu, M. L.; Ge, J.; Li, B.; He, L. Org. Chem. Front. 2022, 9, 1593. |
/
| 〈 |
|
〉 |
