过渡金属催化砜的脱硫交叉偶联反应的研究进展
Research Progress in Transition Metal Catalyzed Desulfurization Cross-Coupling Reactions of Sulfone
DOI: 10.12677/AAC.2023.132024, PDF,   
作者: 段璐琼, 黄晓雷*:浙江师范大学化学与材料科学学院,浙江 金华
关键词: 过渡金属催化有机砜脱硫交叉偶联Transition Metal-Catalysis Sulfones Desulfurization Cross-Coupling
摘要: 近年来,有机砜作为新型交叉偶联试剂在过渡金属催化反应中的应用成为有机合成领域的研究热点。将砜试剂作为新型偶联底物,可以避免底物的预活化,而且砜基官能团易在温和的条件下引入和脱除,对各种官能团容忍性较好,在有机合成领域具有极高的应用价值。本文主要对近年来不同金属催化的砜的脱硫交叉偶联反应相关研究进行了综述。
Abstract: In recent years, the application of organic sulfones as novel cross coupling reagents in transition metal catalyzed reactions has become a research hotspot in the field of organic synthesis. Using sulfone reagents as a novel coupling substrate can avoid the pre activation of the substrate, and sulfonyl functional groups can be easily introduced and removed under mild conditions, with good tolerance for various functional groups, which has high application value in the field of organic synthesis. This article mainly reviews the recent studies on the desulfurization cross coupling reactions of sulfone catalyzed by different metals.
文章引用:段璐琼, 黄晓雷. 过渡金属催化砜的脱硫交叉偶联反应的研究进展[J]. 分析化学进展, 2023, 13(2): 203-215. https://doi.org/10.12677/AAC.2023.132024

参考文献

[1] Sangeetha, S., Muthupandi, P. and Sekar, G. (2015) Copper-Catalyzed Domino Synthesis of 2-Arylthiochromanones through Concomitant C-S Bond Formations Using Xanthate as Sulfur Source. Organic Letters, 17, 6006-6009.
[Google Scholar] [CrossRef] [PubMed]
[2] Correa, A., Carril, M. and Bolm, C. (2008) Iron-Catalyzed S-Arylation of Thiols with Aryl Iodides. Angewandte Chemie International Edition, 47, 2880-2883.
[Google Scholar] [CrossRef] [PubMed]
[3] Itoh, T. and Mase, T. (2007) A Novel Practical Synthesis of Benzothiazoles via Pd-Catalyzed Thiol Cross-Coupling. Organic Letters, 9, 3687-3689.
[Google Scholar] [CrossRef] [PubMed]
[4] Zhou, J.Y., Tian, R. and Zhu, Y.M. (2021) Nickel-Catalyzed Selective Decarbonylation of α-Amino Acid Thioester: Aminomethylation of Mercaptans. The Journal of Organic Chemistry, 86, 12148-12157.
[Google Scholar] [CrossRef] [PubMed]
[5] Chen, L., Hua, Z., Li, G. and Jin, Z. (2011) Controlling the Facial Selectivity of Asymmetric [4 + 2] Cyclo-Additions: A Concise Synthesis of the cis-Decalin Core Structure of Superstolides A and B. Organic Letters, 13, 3580-3583.
[Google Scholar] [CrossRef] [PubMed]
[6] RaoVolla, C.M. and Vogel, P. (2008) Iron-Catalyzed Desulfinylative C-C Cross-Coupling Reactions of Sulfonyl Chlorides with Grignard Reagents. Angewandte Chemie International Edition, 47, 1305-1307.
[Google Scholar] [CrossRef] [PubMed]
[7] Chu, X. Q., Ge, D., Cui, Y. Y., Shen, Z. L. and Li, C. J., (2021) Desulfonylation via Radical Process: Recent Developments in Organic Synthesis. Chemical Reviews, 121, 12548-12680.
[Google Scholar] [CrossRef] [PubMed]
[8] Nambo, M. and Crudden, C.M. (2021) Transition Metal-Catalyzed Cross-Couplings of Benzylic Sulfone Derivatives. The Chemical Record, 21, 3978-3989.
[Google Scholar] [CrossRef] [PubMed]
[9] Milburn, R.R. and Snieckus, V. (2004) The Tertiary Sulfonamide as a Latent Directed-Metalation Group: Ni0-Catalyzed Reductive Cleavage and Cross-Coupling Reactions of Aryl Sulfonamides with Grignard Reagents. Angewandte Chemie International Edition, 43, 888-891.
[Google Scholar] [CrossRef] [PubMed]
[10] Wu, J.C., Gong, L.B., Xia, Y., Song, R.J., Xie, Y.X. and Li, J.X. (2012) Nickel-Catalyzed Kumada Reaction of Tosylalkanes with Grignard Reagents to Produce Alkenes and Modified Arylketones. Angewandte Chemie International Edition, 51, 9909-9913.
[Google Scholar] [CrossRef] [PubMed]
[11] Chen, L., Lang, H., Fang, L., Yu, J. and Wang, L. (2014) Nickel-Catalyzed Desulfitative Suzuki-Miyaura Cross- Coupling of N, N-Disulfonylmethylamines and Arylboronic Acids. European Journal of Organic Chemistry, 29, 6385- 6389.
[Google Scholar] [CrossRef
[12] Merchant, R.R., Edwards, J.T., Qin, T., Kruszyk, M.M., Bi, C., Che, G., Bao, D.H., Qiao, W., Sun, L., Collins, M.R., Fadeyi, O.O., Gallego, G.M., Mousseau, J.J., Nuhant, P. and Baran, P.S. (2018) Modular Radical Cross-Coupling with Sulfones Enables Access to sp3-Rich (Fluoro) Alkylated Scaffolds. Science, 360, 75-80.
[Google Scholar] [CrossRef] [PubMed]
[13] Ariki, Z.T., Maekawa, Y., Nambo, M. and Crudden, C.M. (2018) Preparation of Quaternary Centers via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Tertiary Sulfones. Journal of the American Chemical Society, 140, 78-81.
[Google Scholar] [CrossRef] [PubMed]
[14] Gong, L., Sun, H.B., Deng, L.F., Zhang, X., Liu, J., Yang, S. and Niu, D. (2019) Ni-Catalyzed Suzuki-Miyaura Cross- Coupling of α-Oxo-Vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers. Journal of the American Chemical Society, 141, 7680-7686.
[Google Scholar] [CrossRef] [PubMed]
[15] Hughes, J.M.E. and Fier, P.S. (2019) Desulfonylative Arylation of Redox-Active Alkyl Sulfones with Aryl Bromides. Organic Letters, 21, 5650-5654.
[Google Scholar] [CrossRef] [PubMed]
[16] Miao, W., Ni, C., Xiao, P., Jia, R. and Hu, J. (2021) Nickel-Catalyzed Reductive 2-Pyridination of Aryl Iodides with Difluoromethyl 2-Pyridyl Sulfone. Organic Letters, 23, 711-715.
[Google Scholar] [CrossRef] [PubMed]
[17] Ramberg, L. and Bäcklund, B. (1940) The Reactions of Some Monohalogen Derivatives of Diethyl Sulfone. Arkiv för Kemi, Mineralogi Och Geologi, 13A, 1-50.
[18] Takahashi, F., Nogi, K. and Yorimitsu, H. (2018) Intramolecular Desulfitative Coupling: Nickel-Catalyzed Transformation of Diaryl Sulfones into Biaryls via Extrusion of SO2. Organic Letters, 20, 6601-6605.
[Google Scholar] [CrossRef] [PubMed]
[19] Yu, T.Y., Zheng, Z.J., Bai, J.H., Fang, H. and Wei, H. (2019) Nickel-Catalyzed Intramolecular Coupling of Sulfones via the Extrusion of Sulfur Dioxide. Advanced Synthesis & Catalysis, 361, 2020-2024.
[Google Scholar] [CrossRef
[20] Nambo, M. and Crudden, C.M. (2014) Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone. Angewandte Chemie International Edition, 53, 742-746.
[Google Scholar] [CrossRef] [PubMed]
[21] Nambo, M., Keske, E.C., Rygus, J.P.G., Yim, J. C.H. and Crudden, C.M. (2017) Development of Versatile Sulfone Electrophiles for Suzuki—Miyaura Cross-Coupling Reactions. ACS Catalysis, 7, 1108-1112.
[Google Scholar] [CrossRef
[22] Nambo, M., Yim, J.C., Freitas, L.B.O., Tahara, Y., Ariki, Z.T., Maekawa, Y., Yokogawa, D. and Crudden C.M. (2019) Modular Synthesis of α-Fluorinated Arylmethanes via Desulfonylative Cross-Coupling. Nature Communications, 10, Article No. 4528.
[Google Scholar] [CrossRef] [PubMed]
[23] Chatelain, P., Sau, A., Rowley, C.N. and Moran, J. (2019) Suzuki-Miyaura Coupling of (Hetero) Aryl Sulfones: Complementary Reactivity Enables Iterative Polyaryl Synthesis. Angewandte Chemie International Edition, 58, 14959- 14963.
[Google Scholar] [CrossRef] [PubMed]
[24] Markovic, T., Murray, P.R.D., Rocke, B.N., Shavnya, A., Blakemore, D.C. and Willis, M.C. (2018) Heterocyclic Allylsulfones as Latent Heteroaryl Nucleophiles in Palladium-Catalyzed Cross-Coupling Reactions. Journal of the American Chemical Society, 140, 15916-15923.
[Google Scholar] [CrossRef] [PubMed]
[25] Dang, H.T., Nguyen, V.D., Pham, H.H., Arman, H.D. and Larionov, O.V. (2019) Highly Stereoselective and Catalytic Desulfitative C-O and C-I Dienylation with Sulfolenes: The Importance of Basic Additives. Tetrahedron, 75, 3258- 3264.
[Google Scholar] [CrossRef] [PubMed]
[26] Ren, R., Wu, Z., Xu, Y. and Zhu, C. (2016) C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring- Opening Cyanation and Ethynylation of Cyclobutanol Derivatives. Angewandte Chemie International Edition, 55, 2866-2869.
[Google Scholar] [CrossRef] [PubMed]
[27] Miao, W., Zhao, Y., Ni, C., Bing, G., Wei, Z. and Hu, J. (2018) Iron-Catalyzed Difluoromethylation of Arylzincs with Difluoromethyl 2-Pyridyl Sulfone. Journal of the American Chemical Society, 140, 880-883.
[Google Scholar] [CrossRef] [PubMed]