钯催化构建C-P键反应的研究进展
Research Progress in Palladium Catalyzed C-P Bond Construction Reaction
DOI: 10.12677/jocr.2024.123042, PDF,   
作者: 姬鸿森, 吴新星*:南通大学,化学化工学院,江苏 南通;姚 龙*:南通大学,南通大学分析测试中心,江苏 南通
关键词: 钯催化有机磷化合物C-P键有机合成Palladium-Catalyzed Organic Phosphorus Compounds C-P Bonds Organic Synthesis
摘要: 有机磷化合物因其在药物化学、材料化学和有机化学领域的广泛应用,以及作为配体和有机催化剂在有机合成中的显著地位而受到越来越多的关注。通过钯催化构建C-P键的反应,可以将简单底物转化为结构复杂的有机磷化合物,实现具有重要化学价值的化学转化。根据构建的C-P键类型不同,本文对近年来基于过渡金属钯催化的反应策略合成有机磷化合物的反应及关键反应机理进行了综述和探讨,并展望该研究领域的未来发展前景。
Abstract: Organic phosphorus compounds have received increasing attention due to their widespread applications in pharmaceutical chemistry, material chemistry, and organic chemistry, as well as their outstanding position as ligands and organic catalysts in organic synthesis. The palladium catalyzed C-P bond construction reaction can convert simple substrates into structurally complex organic phosphorus compounds, achieving chemical transformations with significant chemical value. According to the different types of reactions, the synthesis of organophosphorus compounds base on palladium-catalyzed reaction strategies in recent years and the key reaction mechanisms were reviewed and discussed, and the future development prospect of this research field was prospected.
文章引用:姬鸿森, 姚龙, 吴新星. 钯催化构建C-P键反应的研究进展[J]. 有机化学研究, 2024, 12(3): 446-458. https://doi.org/10.12677/jocr.2024.123042

参考文献

[1] Monge, S., Canniccioni, B., Graillot, A. and Robin, J. (2011) Phosphorus-Containing Polymers: A Great Opportunity for the Biomedical Field. Biomacromolecules, 12, 1973-1982. [Google Scholar] [CrossRef] [PubMed]
[2] Quílez-Bermejo, J., Ghisolfi, A., Grau-Marín, D., San-Fabián, E., Morallón, E. and Cazorla-Amorós, D. (2019) Post-synthetic Efficient Functionalization of Polyaniline with Phosphorus-Containing Groups. Effect of Phosphorus on Electrochemical Properties. European Polymer Journal, 119, 272-280. [Google Scholar] [CrossRef
[3] Strasser, P. and Teasdale, I. (2020) Main-Chain Phosphorus-Containing Polymers for Therapeutic Applications. Molecules, 25, Article No. 1716. [Google Scholar] [CrossRef] [PubMed]
[4] Zhao, R.Y., Erickson, H.K., Leece, B.A., Reid, E.E., Goldmacher, V.S., Lambert, J.M., et al. (2012) Synthesis and Biological Evaluation of Antibody Conjugates of Phosphate Prodrugs of Cytotoxic DNA Alkylators for the Targeted Treatment of Cancer. Journal of Medicinal Chemistry, 55, 766-782. [Google Scholar] [CrossRef] [PubMed]
[5] Sullivan, I. and Planchard, D. (2017) Targeting ALK-Rearranged Non-Small-Cell Lung Cancer: An Update. Future Oncology, 13, 1213-1217. [Google Scholar] [CrossRef] [PubMed]
[6] Hodge, R.L., Kaduk, J.A., Gindhart, A.M. and Blanton, T.N. (2021) Crystal Structure of Brigatinib Form A (Alunbrig®), C29H39ClN7O2P. Powder Diffraction, 36, 262-269. [Google Scholar] [CrossRef
[7] Falagas, M.E., Vouloumanou, E.K., Samonis, G. and Vardakas, K.Z. (2016) Fosfomycin. Clinical Microbiology Reviews, 29, 321-347. [Google Scholar] [CrossRef] [PubMed]
[8] Edwards, J.E., Bequette, B.J., McKain, N., McEwan, N.R. and Wallace, R.J. (2005) Influence of Flavomycin on Microbial Numbers, Microbial Metabolism and Gut Tissue Protein Turnover in the Digestive Tract of Sheep. British Journal of Nutrition, 94, 64-70. [Google Scholar] [CrossRef] [PubMed]
[9] Huang, Y., Zhu, Y., Yue, H., Liu, Y., Deng, L., Lv, L., et al. (2024) Flavomycin Restores Colistin Susceptibility in Multidrug-Resistant Gram-Negative Bacteria. mSystems, 9, e00109-24. [Google Scholar] [CrossRef] [PubMed]
[10] Asselah, T. (2013) Sofosbuvir for the Treatment of Hepatitis C Virus. Expert Opinion on Pharmacotherapy, 15, 121-130. [Google Scholar] [CrossRef] [PubMed]
[11] Surial, B., Mugglin, C., Calmy, A., Cavassini, M., Günthard, H.F., Stöckle, M., et al. (2021) Weight and Metabolic Changes after Switching from Tenofovir Disoproxil Fumarate to Tenofovir Alafenamide in People Living with HIV: A Cohort Study. Annals of Internal Medicine, 174, 758-767. [Google Scholar] [CrossRef] [PubMed]
[12] Byun, K.S., Choi, J., Kim, J., Lee, Y.S., Lee, H.C., Kim, Y.J., et al. (2022) Tenofovir Alafenamide for Drug-Resistant Hepatitis B: A Randomized Trial for Switching from Tenofovir Disoproxil Fumarate. Clinical Gastroenterology and Hepatology, 20, 427-437.e5. [Google Scholar] [CrossRef] [PubMed]
[13] Hong, G., Gan, X., Leonhardt, C., Zhang, Z., Seibert, J., Busch, J.M., et al. (2021) A Brief History of OLEDs—Emitter Development and Industry Milestones. Advanced Materials, 33, Article ID: 2005630. [Google Scholar] [CrossRef] [PubMed]
[14] You, X., Gao, J., Duan, Y., Geng, Y., Zhang, M., Zhao, L., et al. (2022) A Theoretical Analysis on the Electron and Energy Transfer between Host and Guest Materials in Phosphor-Doped OLED. Journal of Photochemistry and Photobiology A: Chemistry, 432, Article ID: 114058. [Google Scholar] [CrossRef
[15] Hou, C., Ren, Y., Lang, R., Hu, X., Xia, C. and Li, F. (2012) Palladium-Catalyzed Direct Phosphonation of Azoles with Dialkyl Phosphites. Chemical Communications, 48, 5181-5183. [Google Scholar] [CrossRef] [PubMed]
[16] Berger, O., Petit, C., Deal, E.L. and Montchamp, J. (2013) Phosphorus-Carbon Bond Formation: Palladium-Catalyzed Cross-Coupling of H-Phosphinates and Other P(O)H-Containing Compounds. Advanced Synthesis & Catalysis, 355, 1361-1373. [Google Scholar] [CrossRef
[17] Dong, J., Liu, L., Ji, X., Shang, Q., Liu, L., Su, L., et al. (2019) General Oxidative Aryl C-P Bond Formation through Palladium-Catalyzed Decarbonylative Coupling of Aroylhydrazides with P(O)H Compounds. Organic Letters, 21, 3198-3203. [Google Scholar] [CrossRef] [PubMed]
[18] Chen, X., Liu, X., Zhu, H. and Wang, Z. (2021) Palladium-Catalyzed C-P Bond Activation of Aroyl Phosphine Oxides without the Adjacent “Anchoring Atom”. Tetrahedron, 81, Article ID: 131912. [Google Scholar] [CrossRef
[19] Chen, X., Wu, H., Yu, R., Zhu, H. and Wang, Z. (2021) Palladium-Catalyzed C-P(III) Bond Formation by Coupling ArBr/ArOTf with Acylphosphines. The Journal of Organic Chemistry, 86, 8987-8996. [Google Scholar] [CrossRef] [PubMed]
[20] Chen, C., Ding, J., Liu, L., Huang, Y. and Zhu, B. (2021) Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics. Advanced Synthesis & Catalysis, 364, 200-205. [Google Scholar] [CrossRef
[21] Chen, Z., Pang, W.H., Yuen, O.Y., Ng, S.S. and So, C.M. (2024) Palladium-Catalyzed Chemoselective Phosphorylation of Poly(pseudo)halides: A Route for Organophosphorus Synthesis. The Journal of Organic Chemistry. [Google Scholar] [CrossRef] [PubMed]
[22] Matsude, A., Hirano, K. and Miura, M. (2018) Palladium-Catalyzed Benzylic Phosphorylation of Diarylmethyl Carbonates. Organic Letters, 20, 3553-3556. [Google Scholar] [CrossRef] [PubMed]
[23] Chen, L., Zhou, Z., Zhang, S., Li, X., Ma, X. and Dong, J. (2019) Palladium(II)-Catalyzed Oxidative C(sp3)-P Bond Formation via C(sp3)-H Bond Activation. Chemical Communications, 55, 13693-13696. [Google Scholar] [CrossRef] [PubMed]
[24] Weng, J., Xing, L., Hou, W., Liang, R. and Jia, Y. (2019) Palladium-Catalyzed Dearomative Arylphosphorylation of Indoles. Organic Chemistry Frontiers, 6, 1577-1580. [Google Scholar] [CrossRef
[25] Zhang, P., Ying, J., Tang, G. and Zhao, Y. (2017) Phosphinodifluoroalkylation of Alkynes Using P(O)H Compounds and Ethyl Difluoroiodoacetate. Organic Chemistry Frontiers, 4, 2054-2057. [Google Scholar] [CrossRef
[26] Hu, S., Sun, W., Chen, J., Li, S., Zhao, R., Xu, P., et al. (2021) Palladium-Catalyzed C-P Cross-Coupling of Allenic Alcohols with H-Phosphonates Leading to 2-Phosphinoyl-1,3-butadienes. Chemical Communications, 57, 339-342. [Google Scholar] [CrossRef] [PubMed]
[27] Sun, J., Ye, H., Sun, F., Pan, Y., Zhu, X. and Wu, X. (2023) Palladium-Catalyzed Allylation of P(O)H Compounds: Access to 2-Fluoroallylic Phosphorus Compounds. Organic Letters, 25, 5220-5225. [Google Scholar] [CrossRef] [PubMed]
[28] Huang, H., Wu, Y., Han, L., Jiang, L., Zhang, Z., Zhang, X., et al. (2024) Palladium-Catalyzed (z)-Selective Allylation of Phosphine Oxides with Vinylethylene Carbonates to Construct Phosphorus Allyl Alcohols. Organic & Biomolecular Chemistry, 22, 3068-3072. [Google Scholar] [CrossRef] [PubMed]
[29] Ramesh, K. and Satyanarayana, G. (2019) Microwave-Assisted Domino Heck Cyclization and Phosphorylation: Synthesis of Phosphorus Containing Heterocycles. European Journal of Organic Chemistry, 2019, 3856-3866. [Google Scholar] [CrossRef
[30] Hong, Y., Liu, W., Dong, M., Chen, X., Xu, T., Tian, P., et al. (2019) Pd(0)-Catalyzed Cyclizative Phosphorylation of (z)-1-Iodo-1,6-Diene: Synthesis of Alkylphosphonate and Alkylthionophosphonate. Organic Letters, 21, 5742-5746. [Google Scholar] [CrossRef] [PubMed]
[31] Zhang, M., Ma, Z., Du, H. and Wang, Z. (2020) Palladium-Catalyzed C(sp3)-P(III) Bond Formation Reaction with Acylphosphines as Phosphorus Source. Tetrahedron Letters, 61, 152125. [Google Scholar] [CrossRef
[32] Pan, Y., Zhu, X., Shi, L., Jiang, G. and Wu, X. (2023) Palladium-Catalyzed Heck Cyclization with P(O)H Compounds to Construct Phosphinonyl-Azaindoline and-Azaoxindole Derivatives. The Journal of Organic Chemistry, 88, 9843-9852. [Google Scholar] [CrossRef] [PubMed]