二氧化硫替代物参与的过渡金属催化偶联反应合成有机砜化合物
Synthesis of Organic Sulfones by Transition Metal-Catalyzed Coupling of SO2 Surrogates
DOI: 10.12677/AAC.2023.132027, PDF,   
作者: 卢瑶瑶：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；二氧化硫替代物；有机砜化合物；Transition Metal Catalysis； SO2 Surrogates； Organic Sulfones
摘要: 由于二氧化硫替代物具有简单易得、经济安全、操作简便等特点，因此通过二氧化硫替代物将二氧化硫引入有机框架来构建砜的策略引起了有机化学家们的广泛兴趣。近年来，过渡金属催化偶联反应越来越多的被用于机硫醚、亚砜以及砜等化合物的简洁合成。本文主要围绕基于过渡金属催化二氧化硫插入的偶联反应制备有机砜化合物这一主题进行了综述。
Abstract: Due to the characteristics of SO2 surrogates, such as simplicity, economy, safety, and ease of operation, the strategy of introducing SO2 into organic frameworks to construct sulfones through SO2 surrogates has attracted widespread interest among organic chemists. In recent years, transition metal-catalyzed coupling reactions have increasingly been used for the concise synthesis of organic sulfides, sulfoxides, and sulfones. This article reviews the topic of preparing organic sulfone compounds based on transition metal-catalyzed sulfur dioxide insertion coupling reactions of SO2 surrogates.
文章引用：卢瑶瑶. 二氧化硫替代物参与的过渡金属催化偶联反应合成有机砜化合物[J]. 分析化学进展, 2023, 13(2): 232-241. https://doi.org/10.12677/AAC.2023.132027

参考文献

[1] Zhang, Q.Q., Ying, G.G. and Pan, C.G. (2015) Comprehensive Evaluation of Antibiotics Emission and Fate in the River Basins of China: Source Analysis, Multimedia Modeling and Linkage to Bacterial Resistance. Environmental Science & Technology, 49, 6772-6782.
[Google Scholar] [CrossRef] [PubMed]
[2] Phillips, I., Casewell, M. and Cox, T. (2004) Does the Use of Antibiotics in Food Animals Pose a Risk to Human Health A Critical Review of Published Data. Journal of Antimicrobial Chemotherapy, 53, 28-52.
[Google Scholar] [CrossRef] [PubMed]
[3] Ye, S., Yang, M. and Wu, J. (2020) Recent Advances in Sulfonylation Reactions Using Potassium/Sodium Metabisulfite. Chemical Communications, 56, 4145-4155.
[Google Scholar] [CrossRef] 
[4] Blum, S.P., Hofman, K., Manolikakes, G. and Waldvogel, S.R. (2021) Advances in Photochemical and Electrochemical Incorporation of Sulfur Dioxide for the Synthesis of Value-Added Compounds. Chemical Communications, 57, 8236- 8249.
[Google Scholar] [CrossRef] 
[5] Shavnya, A., Coffey, S.B. and Smith, A.C. (2013) Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides. Organic Letters, 15, 6226-6229.
[Google Scholar] [CrossRef] [PubMed]
[6] Emmett, E.J., Hayter, B.R. and Willis, M.C. (2014) Palladium-Catalyzed Synthesis of Ammonium Sulfinates from Aryl Halides and a Sulfur Dioxide Surrogate: A Gas- and Reductant-Free Process. Angewandte Chemie International Edition, 53, 10204-10208.
[Google Scholar] [CrossRef] [PubMed]
[7] Davies, A.T., Curto, J.M. and Bagley, S.W. (2017) One-Pot Palladium-Catalyzed Synthesis of Sulfonyl Fluorides from Aryl Bromides. Chemical Science, 8, 1233-1237.
[Google Scholar] [CrossRef] 
[8] Emmett, E.J., Hayter, B.R. and Willis, M.C. (2013) Palladium-Catalyzed Three-Component Diaryl Sulfone Synthesis Exploiting the Sulfur Dioxide Surrogate DABSO. Angewandte Chemie International Edition, 52, 12679-12683.
[Google Scholar] [CrossRef] [PubMed]
[9] Johnson, M.W., Bagley, S.W., Mankad, N.P., Bergman, R.G., Mascitti, V. and Toste, F.D. (2014) Application of Fundamental Organometallic Chemistry to the Development of a Gold-Catalyzed Synthesis of Sulfinate Derivatives. Angewandte Chemie International Edition, 53, 4404-4407.
[Google Scholar] [CrossRef] [PubMed]
[10] Zhu, H., Shen, Y., Deng, Q., Chen, J. and Tu, T. (2017) Pd(NHC)-Catalyzed Alkylsulfonylation of Boronic Acids: A General and Efficient Approach for Sulfone Synthesis. Chemical Communications, 53, 12473-12476.
[Google Scholar] [CrossRef] 
[11] Deeming, A.S., Russell, C.J. and Willis, M.C. (2016) Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation. Angewandte Chemie International Edition, 55,747-775.
[Google Scholar] [CrossRef] [PubMed]
[12] Chen, Y. and Willis, M.C. (2017) Copper(I)-Catalyzed Sulfonylative Suzuki-Miyaura Cross-Coupling. Chemical Science, 8, 3249-3253.
[Google Scholar] [CrossRef] 
[13] Lo, P.K.T., Chen, Y. and Willis, M.C. (2019) Nickel(II)-Catalyzed Synthesis of Sulfinates from Aryl and Heteroaryl Boronic Acids and the Sulfur Dioxide Surrogate DABSO. ACS Catalysis, 9, 10668-10673.
[Google Scholar] [CrossRef] 
[14] Zheng, D., Mao, R. and Wu, J. (2016) A General Route to Sulfones via Insertion of Sulfur Dioxide Promoted by Cobalt Oxide. Organic Chemistry Frontiers, 3, 985-999.
[Google Scholar] [CrossRef] 
[15] Nguyen, B., Emmett, E.J. and Willis, M.C. (2010) Palladium-Catalyzed Aminosulfonylation of Aryl Halides. Journal of the American Chemical Society, 132, 16372-16373.
[Google Scholar] [CrossRef] 
[16] Ye, S. and Wu, J., (2012) A Palladium-Catalyzed Reaction of Aryl Halides, Potassium Metabisulfite and Hydrazine. Chemical Communications, 48, 10037-10039.
[Google Scholar] [CrossRef] [PubMed]
[17] Chen, Y., Murray, P.R.D. and Willis, M.C. (2018) Direct Copper-Catalyzed Three-Component Synthesis of Sulfonamides. Journal of the American Chemical Society, 140, 8781-8787.
[Google Scholar] [CrossRef] [PubMed]
[18] Shavnya, A., Hesp, K.D. and Smith, A.C. (2015) Palladium-Catalyzed Synthesis of (Hetero)Aryl Alkyl Sulfones from (Hetero)Aryl Boronic Acids, Unactivated Alkyl Halides, and Potassium Metabisulfite. Angewandte Chemie International Edition, 54, 13571-13575.
[Google Scholar] [CrossRef] [PubMed]
[19] Zheng, D., Mao, R., Li, Z. and Wu, J. (2016) A Copper(I)-Catalyzed Three-Component Reaction of Triethoxysilanes, Sulfur Dioxide and Alkyl Halides. Organic Chemistry Frontiers, 3, 359-363.
[Google Scholar] [CrossRef] 
[20] Yang, D., Sun, P., Wei, W., Liu, F., Zhang, H. and Wang, H. (2018) Copper-Catalyzed Regioselective Cleavage of C-X and C-H Bonds: A Strategy for Sulfur Dioxide Fixation. Chemistry: A European Journal, 24, 4423-4427.
[Google Scholar] [CrossRef] [PubMed]
[21] Liu, T., Zhou, W. and Wu, J. (2017) Palladium-Catalyzed Direct C-H Functionalization of Indoles with the Insertion of Sulfur Dioxide: Synthesis of 2-Sulfonated Indoles. Organic Letters, 19, 6638-6641.
[Google Scholar] [CrossRef] [PubMed]
[22] Xia, H., An, Y., Zeng, X. and Wu, J. (2017) Palladium-Catalyzed Direct Sulfonylation of C-H Bonds with the Insertion of Sulfur Dioxide. Chemical Communications, 53, 12548-12551.
[Google Scholar] [CrossRef] 
[23] Wang, K., Wang, G., Duan, G. and Xia, C. (2017) Cobalt(II)-Catalyzed Remote C5-Selective C-H Sulfonylation of Quinolines via Insertion of Sulfur Dioxide. RSC Advances., 7, 51313-51317.
[Google Scholar] [CrossRef] 
[24] Meng, Y., Wang, M. and Jiang. X. (2020) Multicomponent Reductive Cross-Coupling of an Inorganic Sulfur Dioxide Surrogate: Straightforward Construction of Diversely Functionalized Sulfones. Angewandte Chemie International Edition, 59, 1346-1353.
[Google Scholar] [CrossRef] [PubMed]

为你推荐