可见光光氧化还原催化C-F键断裂的研究进展
Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis
DOI: 10.12677/jocr.2024.121011, PDF,   
作者: 张菲杰:浙江师范大学,化学与材料科学学院,浙江 金华
关键词: 可见光自由基C-F键裂解光氧化还原Visible Light Radical C-F Bond Cleavage Photoredox
摘要: 通过容易获得的单氟或低氟化合物的C-F键裂解来产生新键受到越来越多的科学家的关注。通过这种方法,可以制备出很多有价值的氟化产品,传统的C-F键形成方法很难制造这些产品。可见光光氧化还原催化由于其温和、易于处理和环境友好的特性,已被证明是脱氟反应的重要而强大的工具。与通过双电子过程进行的经典C-F活化相比,自由基是使用可见光光氧化还原催化的关键中间体,为C-F键的断裂提供了新的方式。在这篇综述中,总结了自2018年以来可见光促进的C-F键断裂的偕-二氟烯烃、三氟甲基芳烃和三氟甲基烯烃。
Abstract: The generation of new bonds by C-F bond cleavage of readily available monofluorinated or low-fluorinated compounds has received increasing attention from scientists. By this method, many valuable fluorinated products can be prepared, which are difficult to make with traditional C-F bond formation methods. Visible light photoredox catalysis has proven to be an important and powerful tool for defluorination reactions due to its mild, easy to handle and environmentally friendly properties. In contrast to classical C-F activation via a two-electron process, free radicals are key intermediates catalyzed by photoredox using visible light, providing a new mode for C-F bond breaking. In this review, GEM-difluoroolefins, trifluoromethylarenes, and trifluoromethylolefins with visible-facilitated C-F bond breakage since 2018 are summarized.
文章引用:张菲杰. 可见光光氧化还原催化C-F键断裂的研究进展[J]. 有机化学研究, 2024, 12(1): 136-147. https://doi.org/10.12677/jocr.2024.121011

参考文献

[1] Kirsch, P. (2004) Modern Fluoroorganic Chemistry: Synthesis Reactivity, Applications. Wiley-VCH, Weinheim. [Google Scholar] [CrossRef
[2] Wang, B., Wang, C.-T., Li, X.-S., Sun, W.-H., Liu, X.-Y. and Liang, Y.-M. (2023) Visible-Light-Mediated C-F Bond Cleavage for the Synthesis of Polyfluorinated Compounds. Organic Chemistry Frontiers, 10, 3341-3346. [Google Scholar] [CrossRef
[3] Berger, R., Resnati, G., Metrangolo, P., Weber, E. and Hulliger, J. (2011) Organic Fluorine Compounds: A Great Opportunity for Enhanced Materials Properties. Chemical Society Reviews, 40, 3496-3508. [Google Scholar] [CrossRef] [PubMed]
[4] Gillis, E.P., Eastman, K.J., Hill, M.D., Donnelly, D.J. and Meanwell, N.A. (2015) Applications of Fluorine in Medicinal Chemistry. Journal of Medicinal Chemistry, 58, 8315-8359. [Google Scholar] [CrossRef] [PubMed]
[5] Sicard, A.J. and Baker, R.T. (2020) Fluorocarbon Refrigerants and their Syntheses: Past to Present. Chemical Reviews, 120, 9164-9303. [Google Scholar] [CrossRef] [PubMed]
[6] Stahl, T., Klare, H.F.T. and Oestreich, M. (2013) Main-Group Lewis Acids for C-F Bond Activation. ACS Catalysis, 3, 1578-1587. [Google Scholar] [CrossRef
[7] Kuehnel, M.F., Lentz, D. and Braun, T. (2013) Synthesis of Fluorinated Building Blocks by Transition-Metal-Mediated Hydrodefluorination Reactions. Angewandte Chemie International Edition, 52, 3328-3348. [Google Scholar] [CrossRef] [PubMed]
[8] Ahrens, T., Kohlmann, J., Ahrens, M. and Braun, T. (2015) Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C-F Bond Activation to Access Fluorinated Building Blocks. Chemical Reviews, 115, 931-972. [Google Scholar] [CrossRef] [PubMed]
[9] Unzner, T.A. and Magauer, T. (2015) Carbon-Fluorine Bond Activation for the Synthesis of Functionalized Molecules. Tetrahedron Letters, 56, 877-883. [Google Scholar] [CrossRef
[10] Hamel, J.-D. and Paquin, J.-F. (2018) Activation of C-F Bonds α to C-C Multiple Bonds. Chemical Communications, 54, 10224-10239. [Google Scholar] [CrossRef
[11] Jaroschik, F. (2018) Picking One out of Three: Selective Single C-F Activation in Trifluoromethyl Groups. ChemistryA European Journal, 24, 14572-14582. [Google Scholar] [CrossRef] [PubMed]
[12] Fujita, T., Fuchibe, K. and Ichikawa, J. (2019) Transition-Metal-Mediated and-Catalyzed C-F Bond Activation by Fluorine Elimination. Angewandte Chemie International Edition, 58, 390-402. [Google Scholar] [CrossRef] [PubMed]
[13] Key, B.D., Howell, R.D. and Criddle, C.S. (1997) Fluorinated Organics in the Biosphere. Environmental Science & Technology, 31, 2445-2454. [Google Scholar] [CrossRef
[14] Prier, C.K., Rankic, D.A. and MacMillan, D.W.C. (2013) Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis. Chemical Reviews, 113, 5322-5363. [Google Scholar] [CrossRef] [PubMed]
[15] Skubi, K.L., Blum, T.R. and Yoon, T.P. (2016) Dual Catalysis Strategies in Photochemical Synthesis. Chemical Reviews, 116, 10035-10074. [Google Scholar] [CrossRef] [PubMed]
[16] Zhou, L., Hossain, M.L. and Xiao, T. (2016) Synthesis of N-Containing Heterocyclic Compounds Using Visible-Light Photoredox Catalysis. The Chemical Record, 16, 319-334. [Google Scholar] [CrossRef] [PubMed]
[17] Sharma, S., Singh, J. and Sharma, A. (2021) Visible Light Assisted Radical-Polar/Polar-Radical Crossover Reactions in Organic Synthesis. Advanced Synthesis & Catalysis, 363, 3146-3169. [Google Scholar] [CrossRef
[18] Zhou, L. and Anand, D. (2019) Visible Light-Mediated C-F Bond Activation. In: Postigo, A., Ed., Late-Stage Fluorination of Bioactive Molecules and Biologically Relevant Substrates, Elsevier, Amsterdam, 159-181. [Google Scholar] [CrossRef
[19] Singh, A., Fennell, C.J. and Weaver, J.D. (2016) Photocatalyst Size Controls Electron and Energy Transfer: Selectable E/Z Isomer Synthesisvia C-F Alkenylation. Chemical Science, 7, 6796-6802. [Google Scholar] [CrossRef
[20] Senaweera, S. and Weaver, J.D. (2016) Dual C-F, C-H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls. Journal of the American Chemical Society, 138, 2520-2523. [Google Scholar] [CrossRef] [PubMed]
[21] Priya, S. and Weaver, J.D. (2018) Prenyl Praxis: A Method for Direct Photocatalytic Defluoroprenylation. Journal of the American Chemical Society, 140, 16020-16025. [Google Scholar] [CrossRef] [PubMed]
[22] Doi, R., et al. (2023) Regioselective C-F Bond Transformations of Silyl Difluoroenolates. Organic Letters, 25, 5542-5547. [Google Scholar] [CrossRef] [PubMed]
[23] You, M.W., Bian, T.C., Zhou, L.J. and Zhang, Z.X. (2023) Accessing Aryldifluoromethyl Derivatives through Alkene Insertion into Benzylic C-F Bonds. Synlett, 34, 1747-1751. [Google Scholar] [CrossRef
[24] Day, J.I., Grotjahn, S., Senaweera, S., Koenig, B. and Weaver, J.D. (2021) Defluorodearomatization: A Photocatalytic Birch-Like Reduction That Enables C-C Bond Formation and Provides Access to Unnatural Cannabinoids. The Journal of Organic Chemistry, 86, 7928-7945. [Google Scholar] [CrossRef] [PubMed]
[25] Xie, J., Yu, J., Rudolph, M., Rominger, F. and Hashmi, A.S.K. (2016) Monofluoroalkenylation of Dimethylamino Compounds through Radical-Radical Cross-Coupling. Angewandte Chemie International Edition, 55, 9416-9421. [Google Scholar] [CrossRef] [PubMed]
[26] Wang, Q., Qu, Y., Tian, H., Liu, Y., Song, H. and Wang, Q. (2019) Trifluoromethylation and Monofluoroalkenylation of Alkenes through Radical-Radical Cross-Coupling. ChemistryA European Journal, 25, 8686-8690. [Google Scholar] [CrossRef] [PubMed]
[27] Wang, J., Huang, B., Yang, C. and Xia, W. (2019) Visible-Light-Mediated Defluorinative Cross-Coupling of gem-Difluoroalkenes with Thiols. Chemical Communications, 55, 11103-11106. [Google Scholar] [CrossRef
[28] Wang, J., Huang, B., Gao, Y., Yang, C. and Xia, W. (2019) Direct C-H Multifluoroarylation of Ethers through Hydrogen Atom Transfer Using Photoredox Catalysis. The Journal of Organic Chemistry, 84, 6895-6903. [Google Scholar] [CrossRef] [PubMed]
[29] Orsi, D.L., Easley, B.J., Lick, A.M. and Altman, R.A. (2017) Base Catalysis Enables Access to α, α-Difluoroalkylthioethers. Organic Letters, 19, 1570-1573. [Google Scholar] [CrossRef] [PubMed]
[30] Dénès, F., Pichowicz, M., Povie, G. and Renaud, P. (2014) Thiyl Radicals in Organic Synthesis. Chemical Reviews, 114, 2587-2693. [Google Scholar] [CrossRef] [PubMed]
[31] Sugihara, N., Suzuki, K., Nishimoto, Y. and Yasuda, M. (2021) Photoredox-Catalyzed C-F Bond Allylation of Perfluoroalkylarenes at the Benzylic Position. Journal of the American Chemical Society, 143, 9308-9313. [Google Scholar] [CrossRef] [PubMed]
[32] Vogt, D.B., Seath, C.P., Wang, H. and Jui, N.T. (2019) Selective C-F Functionalization of Unactivated Trifluoromethylarenes. Journal of the American Chemical Society, 141, 13203-13211. [Google Scholar] [CrossRef] [PubMed]
[33] Xiao, T., Li, L. and Zhou, L. (2016) Synthesis of Functionalized gem-Difluoroalkenes via a Photocatalytic Decarboxylative/Defluorinative Reaction. The Journal of Organic Chemistry, 81, 7908-7916. [Google Scholar] [CrossRef] [PubMed]
[34] Ichikawa, J., Fujiwara, M., Wada, Y., Okauchi, T. and Minami, T. (2000) The Nucleophilic 5-Endo-trig Cyclization of Gem-Difluoroolefins with Homoallylic Functional Groups: Syntheses of Ring-Fluorinated Dihydroheteroaromatics. Chemical Communications, No. 19, 1887-1888. [Google Scholar] [CrossRef
[35] Guo, Y.-Q., Wang, R., Song, H., Liu, Y. and Wang, Q. (2020) Visible-Light-Induced Deoxygenation/Defluorination Protocol for Synthesis of γ, γ-Difluoroallylic Ketones. Organic Letters, 22, 709-713. [Google Scholar] [CrossRef] [PubMed]
[36] Yoshida, T., Ohta, M., Emmei, T., et al. (2023) Cationic Rhodium(I) Tetrafluoroborate Catalyzed Intramolecular Carbofluorination of Alkenes via Acyl Fluoride C-F Bond Activation. Angewandte Chemie, 62, e202303657. [Google Scholar] [CrossRef] [PubMed]
[37] Yu, Y.-J., Zhang, F.-L., Peng, T.-Y., Wang, C.-L., Cheng, J., Chen, C., Houk, K.N. and Wang, Y.-F. (2021) Sequential C-F Bond Functionalizations of Trifluoroacetamides and Acetates via Spin-Center Shifts. Science, 371, 1232-1240. [Google Scholar] [CrossRef] [PubMed]
[38] Hu, Y., Liu, X.C., Ren, Z.Y., et al. (2022) Csp3-H Monofluoroalkenylation via Stereoselective C-F Bond Cleavage. Chemical Communications, 58, 2734-2737. [Google Scholar] [CrossRef
[39] He, Y., Anand, D., Sun, Z. and Zhou, L. (2019) Visible-Light-Promoted Redox Neutral γ, γ-Difluoroallylation of Cycloketone Oxime Ethers with Trifluoromethyl Alkenes via C-C and C-F Bond Cleavage. Organic Letters, 21, 3769-3773. [Google Scholar] [CrossRef] [PubMed]
[40] Zhang, G.D., Wang, L., Cui, L.P., Gao, P. and Chen, F. (2023) Deaminativedefluoroalkylation of α-Trifluoromethylalkenes Enabled by Photoredox Catalysis. Organic & Biomolecular Chemistry, 21, 294-299. [Google Scholar] [CrossRef
[41] Supranovich, V.I., Levin, V.V., Kokorekin, V.A. and Dilman, A.D. (2021) Generation of Alkyl Radicals from Thiols via Zinc Thiolates: Application for the Synthesis of gem-Difluorostyrenes. Advanced Synthesis & Catalysis, 363, 2888-2892. [Google Scholar] [CrossRef
[42] Tian, Q.Q., Pei, B.Q., Wang, C.X., Zhang, C.Y. and Li, Y.H. (2022) Selective C-F Bond Etherification of Trifluoromethyl Alkenes with Phenols The Journal of Organic Chemistry, 87, 10908-10916. [Google Scholar] [CrossRef] [PubMed]
[43] Anand, D., Sun, Z. and Zhou, L. (2020) Visible-Light-Mediated β-C-H gem-Difluoroallylation of Aldehydes and Cyclic Ketones through C-F Bond Cleavage of 1-Trifluoromethyl Alkenes. Organic Letters, 22, 2371-2375. [Google Scholar] [CrossRef] [PubMed]
[44] Kou, L.-G., Guo, S.-H., Gao, Y.-R., et al. (2023) Oxidative Cleavage and Fluoromethylthiolation of C=C Bonds: A General Route toward Mono-, Di-, and Trifluoromethylthioesters from Alkenes. Organic Letters, 25, 5984-5988. [Google Scholar] [CrossRef] [PubMed]