芴衍生物合成研究
Research on the Synthesis of Fluorene Derivatives
DOI: 10.12677/jocr.2025.132022, PDF,    国家自然科学基金支持
作者: 王 旭*, 陈兴楠, 薛梓超, 樊晓辉*:兰州交通大学化学化工学院,甘肃 兰州
关键词: 多环芳烃芴衍生物合成方法Polycyclic Aromatic Hydrocarbons Fluorene Derivatives Synthetic Method
摘要: 芴衍生物(Fluorene)作为多环芳烃(PAHs)家族的重要成员在生物医学、药物研发、光电材料、有机金属催化等领域有着广泛的应用前景。在过去几十年里,芴衍生物的合成引起了合成化学家的广泛关注。鉴于人们对这一领域日益增长的兴趣以及该领域快速发展的研究态势,本文对芴衍生物合成方法的最新进展进行了总结。这篇综述旨在为从事芴衍生物合成的研究人员提供有价值的参考,从而推动该领域的进一步探索和创新。
Abstract: Fluorene derivatives, as important members of the polycyclic aromatic hydrocarbons (PAHs) family, have broad application prospects in biomedical, pharmaceutical research, optoelectronic materials, organometallic catalysis, and other fields. In the past few decades, the synthesis of fluorene derivatives has attracted widespread attention from synthetic chemists. Given the growing interest in this field and the rapidly developing research trend, this article summarizes the latest progress in the synthesis methods of fluorene derivatives. This review aims to provide valuable references for researchers engaged in the synthesis of fluorene derivatives, thereby promoting further exploration and innovation in this field.
文章引用:王旭, 陈兴楠, 薛梓超, 樊晓辉. 芴衍生物合成研究[J]. 有机化学研究, 2025, 13(2): 220-233. https://doi.org/10.12677/jocr.2025.132022

参考文献

[1] Wei, X., Bai, C., Wang, A., Feng, Q., Zhao, L., Zhang, P., et al. (2021) Lewis Acid Enables Ketone Phosphorylation to Form a C-P Bond and a C-C Bond: Synthesis of 9-Phosphoryl Fluorene Derivatives. Organic Letters, 23, 7100-7105. [Google Scholar] [CrossRef] [PubMed]
[2] Banala, A.K., Levy, B.A., Khatri, S.S., Furman, C.A., Roof, R.A., Mishra, Y., et al. (2011) N-(3-Fluoro-4-(4-(2-Methoxy or 2, 3-Dichlorophenyl)piperazine-1-Yl)butyl)Arylcarboxamides as Selective Dopamine D3 Receptor Ligands: Critical Role of the Carboxamide Linker for D3 Receptor Selectivity. Journal of Medicinal Chemistry, 54, 3581-3594. [Google Scholar] [CrossRef] [PubMed]
[3] Beutler, U., Fuenfschilling, P.C. and Steinkemper, A. (2007) An Improved Manufacturing Process for the Antimalaria Drug Coartem. Part II. Organic Process Research & Development, 11, 341-345. [Google Scholar] [CrossRef
[4] Qu, Y. and Li, Y. (2025) Structural Insights and Molecular Advancements in Fluorene-Based Electroluminescent Materials: A Mini-Review. Journal of Molecular Structure, 1330, Article ID: 141466. [Google Scholar] [CrossRef
[5] Justin Thomas, K.R. and Baheti, A. (2013) Fluorene Based Organic Dyes for Dye Sensitised Solar Cells: Structure–property Relationships. Materials Technology, 28, 71-87. [Google Scholar] [CrossRef
[6] Selikhov, A.N., Lapshin, I.V., Cherkasov, A.V., Fukin, G.K. and Trifonov, A.A. (2021) Sandwich and Half-Sandwich Ln(II) (Ln = Sm, Yb) Complexes with Bulky Fluorenyl Ligands. Competitive Abstraction of H or SiMe3 from 2,7-t Bu2-9-SiMe3-Fluorene by an Amido Anion. Organometallics, 40, 3042-3049. [Google Scholar] [CrossRef
[7] Kirillov, E., Dash, A.K., Rodrigues, A. and Carpentier, J. (2006) Ansa-Metallocene and Half-Sandwich Complexes of Group-3 Metals and Lanthanides Incorporating Fluorenyl-Based Ligands: From Synthesis to Catalytic Applications. Comptes Rendus. Chimie, 9, 1151-1157. [Google Scholar] [CrossRef
[8] Liu, X., Luo, H., Huang, Y., Bao, J., Tang, G., Chen, Y., et al. (2013) Selaginpulvilins A-D, New Phosphodiesterase-4 Inhibitors with an Unprecedented Skeleton from Selaginella pulvinata. Organic Letters, 16, 282-285. [Google Scholar] [CrossRef] [PubMed]
[9] Deng, Y., Jiang, K., Cai, M., Qu, S., Dai, Y. and Tan, C. (2017) The Synthesis of Dendroflorin. Journal of Asian Natural Products Research, 19, 602-609. [Google Scholar] [CrossRef] [PubMed]
[10] Luo, Y., Liu, Z., Yang, G., Wang, T., Bin, Z., Lan, J., et al. (2021) Iridium(III)‐Catalyzed Diarylation/Annulation of Benzoic Acids: Facile Access to Multi‐Aryl Spirobifluorenes as Pure Hydrocarbon Hosts for High‐Performance OLEDs. Angewandte Chemie International Edition, 60, 18852-18859. [Google Scholar] [CrossRef] [PubMed]
[11] Shi, G., Chen, D., Jiang, H., Zhang, Y. and Zhang, Y. (2016) Synthesis of Fluorenes Starting from 2-Iodobiphenyls and Ch2Br2 through Palladium-Catalyzed Dual C-C Bond Formation. Organic Letters, 18, 2958-2961. [Google Scholar] [CrossRef] [PubMed]
[12] Cai, Z., Hou, X., Hou, L., Hu, Z., Zhang, B. and Jin, Z. (2015) One-Pot Palladium(II)-Catalyzed Synthesis of Fluorenones via Decarboxylative Cyclization. Synlett, 27, 395-398. [Google Scholar] [CrossRef
[13] Xu, S., Chen, R., Fu, Z., Zhou, Q., Zhang, Y. and Wang, J. (2017) Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(Sp2)-H Bond Functionalization. ACS Catalysis, 7, 1993-1997. [Google Scholar] [CrossRef
[14] Konishi, H., Futamata, S., Wang, X. and Manabe, K. (2018) Rapid Formation of Fluoren‐9‐Ones via Palladium‐Catalyzed External Carbon Monoxide‐Free Carbonylation. Advanced Synthesis & Catalysis, 360, 1805-1809. [Google Scholar] [CrossRef
[15] Ma, D., Shi, G., Wu, Z., Ji, X. and Zhang, Y. (2018) Synthesis of 9, 9-Disubstituted Fluorenes from 2-Iodobiphenyls and α-Diazoesters under Palladium Catalysis. The Journal of Organic Chemistry, 83, 1065-1072. [Google Scholar] [CrossRef] [PubMed]
[16] Liu, X., Sheng, H., Zhou, Y. and Song, Q. (2021) Pd-Catalyzed Assembly of Fluoren-9-Ones by Merging of C-H Activation and Difluorocarbene Transfer. Organic Letters, 23, 2543-2547. [Google Scholar] [CrossRef] [PubMed]
[17] Sun, D., Li, B., Lan, J., Huang, Q. and You, J. (2016) Chelation-Assisted Pd-Catalysed Ortho-Selective Oxidative C-H/C-H Cross-Coupling of Aromatic Carboxylic Acids with Arenes and Intramolecular Friedel-Crafts Acylation: One-Pot Formation of Fluorenones. Chemical Communications, 52, 3635-3638. [Google Scholar] [CrossRef] [PubMed]
[18] Patel, A., Shaikh, M. and Chikhalia, K. (2019) Palladium Catalyzed Domino C-H Activation Strategy: An Access to 9-Fluorenones. Tetrahedron, 75, 236-245. [Google Scholar] [CrossRef
[19] Fu, W.C. and Kwong, F.Y. (2020) A Denitrogenative Palladium-Catalyzed Cascade for Regioselective Synthesis of Fluorenes. Chemical Science, 11, 1411-1417. [Google Scholar] [CrossRef
[20] Gorin D.J., Watson I.D. and Toste F.D. (2008) Fluorenes and Styrenes by Au(I)-Catalyzed Annulation of Enynes and Alkynes. Journal of the American Chemical Society, 130, 3736-3737. [Google Scholar] [CrossRef] [PubMed]
[21] Bucher, J., Wurm, T., Taschinski, S., Sachs, E., Ascough, D., Rudolph, M., et al. (2016) Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes. Advanced Synthesis & Catalysis, 359, 225-233. [Google Scholar] [CrossRef
[22] Wilkerson-Hill, S.M., Lavados, C.M. and Sarpong, R. (2016) The Diels-Alder Reactivity of 2-Vinylindenes: Synthesis of Functionalized Tetrahydrofluorenes. Tetrahedron, 72, 3635-3640. [Google Scholar] [CrossRef
[23] Kaiser, R.P., Hessler, F., Mosinger, J., Císařová, I. and Kotora, M. (2015) A [2 + 2 + 2]‐Cyclotrimerization Approach to Selectively Substituted Fluorenes and Fluorenols, and Their Conversion to 9,9′‐Spirobifluorenes. ChemistryA European Journal, 21, 13577-13582. [Google Scholar] [CrossRef] [PubMed]
[24] Kaiser, R.P., Mosinger, J., Císařová, I. and Kotora, M. (2017) Synthesis of Selectively 4-Substituted 9,9′-Spirobifluorenes and Modulation of Their Photophysical Properties. Organic & Biomolecular Chemistry, 15, 6913-6920. [Google Scholar] [CrossRef] [PubMed]
[25] Ye, F., Haddad, M., Michelet, V. and Ratovelomanana-Vidal, V. (2016) Access toward Fluorenone Derivatives through Solvent-Free Ruthenium Trichloride Mediated [2 + 2 + 2] Cycloadditions. Organic Letters, 18, 5612-5615. [Google Scholar] [CrossRef] [PubMed]
[26] Nishida, M., Lee, D. and Shintani, R. (2020) Intermolecular Three-Component Synthesis of Fluorene Derivatives by a Rhodium-Catalyzed Stitching Reaction/remote Nucleophilic Substitution Sequence. The Journal of Organic Chemistry, 85, 8489-8500. [Google Scholar] [CrossRef] [PubMed]
[27] Hsu, C., Liu, Y. and Liu, S. (2024) Preparation of Benzo[a]Fluorenes via Pd-Catalyzed Annulation of 5-(2-Bromophenyl)Pent-3-En-1-Ynes. The Journal of Organic Chemistry, 89, 12341-12348. [Google Scholar] [CrossRef] [PubMed]
[28] Song, J., Li, Y., Sun, W., Yi, C., Wu, H., Wang, H., et al. (2016) Efficient Palladium-Catalyzed C(sp2)-H Activation Towards the Synthesis of Fluorenes. New Journal of Chemistry, 40, 9030-9033. [Google Scholar] [CrossRef
[29] Corrie, T.J.A., Ball, L.T., Russell, C.A. and Lloyd-Jones, G.C. (2016) Au-Catalyzed Biaryl Coupling to Generate 5-to 9-Membered Rings: Turnover-Limiting Reductive Elimination versus Π-Complexation. Journal of the American Chemical Society, 139, 245-254. [Google Scholar] [CrossRef] [PubMed]
[30] Gao, Q. and Xu, S. (2018) Palladium-catalyzed Synthesis of Fluoreones from Bis(2-Bromophenyl)Methanols. Organic & Biomolecular Chemistry, 16, 208-212. [Google Scholar] [CrossRef] [PubMed]
[31] Fujihara, T., Tanji, Y. and Tsuji, Y. (2020) Palladium-Catalyzed Synthesis of Fluorenes by Intramolecular C(Sp2)-H Activation at Room Temperature. Synlett, 31, 805-808. [Google Scholar] [CrossRef
[32] Zhao, Z., Jameel, I. and Murphy, G.K. (2019) Vicinal Dichlorination of O-Vinylbiphenyls and the Synthesis of 9-(Arylmethyl) Fluo-Renes via Tandem Friedel-Crafts Alkylations. Synthesis, 51, 2648-2659. [Google Scholar] [CrossRef
[33] Jourjine, I.A.P., Zeisel, L., Krauß, J. and Bracher, F. (2021) Synthesis of Highly Substituted Fluorenones via Metal-Free TBHP-Promoted Oxidative Cyclization of 2-(Aminomethyl)Biphenyls. Application to the Total Synthesis of Nobilone. Beilstein Journal of Organic Chemistry, 17, 2668-2679. [Google Scholar] [CrossRef] [PubMed]
[34] Guo, H., Zhang, S., Feng, X., Yu, X., Yamamoto, Y. and Bao, M. (2022) Palladium-Catalyzed Cycloisomerization of 2-Ethynylbiaryls to 9-Methylidene Fluorenes. Organic Letters, 24, 2596-2600. [Google Scholar] [CrossRef] [PubMed]
[35] Matsuyama, H., Zhang, X., Terada, M. and Jin, T. (2023) Construction of Alkylidene Fluorene Scaffolds Using Pd-Catalyzed Direct Arene/Alkene Coupling Strategy. Organic Letters, 25, 800-804. [Google Scholar] [CrossRef] [PubMed]