电化学卤化反应研究进展
Research Progress in Electrochemical Halogenation
DOI: 10.12677/JOCR.2022.104013, PDF,  被引量   
作者: 陈凌杰:兰州交通大学,化学化工学院,甘肃 兰州
关键词: 电化学卤源卤化Electrochemistry Halogen Source Halogenation
摘要: 有机电化学合成被认为是一个环境友好、高效和多用途的合成方法,常用于构建碳–碳和碳–杂原子键。此类方法往往可以避免使用过渡金属催化剂和昂贵的氧化剂,符合“绿色化学”理念。卤化反应在有机合成中占有重要地位,近年来,电化学卤化反应取得了重大进展。本文整理并总结了现有的电化学卤化反应研究。
Abstract: Organic electrochemical synthesis is considered to be an environmentally benign, highly effective and versatile synthesis method, which is often used to construct carbon-carbon and carbon-heteroatom bonds. Such methods can often avoid the use of transition metal catalysts and expensive oxidants, which is in line with the concept of “green chemistry”. Halogenation plays an important role in organic synthesis. In recent years, electrochemical halogenation has made great progress. In this paper, the existing studies on electrochemical halogenation are collected and summarized.
文章引用:陈凌杰. 电化学卤化反应研究进展[J]. 有机化学研究, 2022, 10(4): 127-137. https://doi.org/10.12677/JOCR.2022.104013

参考文献

[1] Butler, A. and Walker, J.V. (1993) Marine Haloperoxidases. Chemical Reviews, 93, 1937-1944. [Google Scholar] [CrossRef
[2] Wan, X.B., Xing, D., Fang, Z., et al. (2006) Multiple Deprotonations and Deaminations of Phenethylamines to Synthesize Pyrroles. Journal of the American Chemical Society, 128, 12046-12047. [Google Scholar] [CrossRef] [PubMed]
[3] Tsuchida, K., Kochi, T. and Kakiuchi, F. (2013) Copper-Catalyzed Electrochemical Chlorination of 1,3-Dicarbonyl Compounds Using Hydrochloric Acid. Asian Journal of Organic Chemistry, 2, 935-937. [Google Scholar] [CrossRef
[4] Kulangiappar, K., Anbukulandainathan, M. and Raju, T. (2014) Nuclear versus Side-Chain Bromination of 4-Methoxy Toluene by an Electrochemical Method. Synthetic Communications, 44, 2494-2502. [Google Scholar] [CrossRef
[5] Kulangiappar, K., Ramprakash, M., Vasudevan, D. and Raju, T. (2016) Electrochemical Bromination of Cyclic and Acyclic Enes Using Biphasic Electrolysis. Synthetic Communications, 46, 145-153. [Google Scholar] [CrossRef
[6] Yuan, Y., Yao, A.J., Zheng, Y.F., et al. (2019) Electrochemical Oxidative Clean Halogenation Using HX/NaX with Hydrogen Evolution. iScience, 12, 293-303. [Google Scholar] [CrossRef] [PubMed]
[7] Park, J.W., Kim, Y.H. and Kim, D.Y. (2020) Electrochemical Oxidative Iodination of Imidazo[1,2-a]pyridines Using NaI as Iodine Source. Synthetic Communications, 50, 710-718. [Google Scholar] [CrossRef
[8] Yu, D., Ji, R.X., Sun, Z.H., Li, W.J. and Liu, Z.Q. (2021) Electrochemical Chlorination and Bromination of Electron-Deficient C-H Bonds in Quinones, Coumarins, Quinoxalines and 1,3-Diketones. Tetrahedron Letters, 86, Article ID: 153514. [Google Scholar] [CrossRef
[9] Kim, R., Ha, J., Woo, J. and Kim, D.Y. (2022) Electrochemical Oxidative Bromolactonization of Unsaturated Carboxylic Acids with Sodium Bromide: Synthesis of Bromomethylated γ-Lactones. Tetrahedron Letters, 88, Article ID: 153567. [Google Scholar] [CrossRef
[10] Liu, X., Wu, Z.Z., Feng, C.L., et al. (2022) Catalyst- and Oxidant-Free Electrochemical Halogenation Reactions of 2H-Indazoles with NaX (X = Cl, Br). European Journal of Organic Chemistry, 2022, e202200262. [Google Scholar] [CrossRef
[11] Wang, Y.L., Simon, H., Chen, X.R., Lin, Z.P., Chen, S. and Ackermann, L. (2022) Distal Ruthenaelectro-Catalyzed Meta-C-H Bromination with Aqueous HBr. Angewandte Chemie International Edition, 61, e202201595. [Google Scholar] [CrossRef] [PubMed]
[12] Jagatheesan, R., Joseph Santhana Raj, K., Lawrence, S. and Christopher, C. (2016) Electroselective α-Bromination of Acetophenone Using in Situ Bromonium Ions from Ammonium Bromide. RSC Advances, 6, 35602-35608. [Google Scholar] [CrossRef
[13] Yang, Q.L., Wang, X.Y., Wang, T.L., et al. (2019) Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent. Organic Letters, 21, 2645-2649. [Google Scholar] [CrossRef] [PubMed]
[14] Yang, X., Yang, Q.L., Wang, X.Y., et al. (2020) Copper-Catalyzed Electrochemical Selective Bromination of 8-Ami- noquinoline Amide Using NH4Br as the Brominating Reagent. The Journal of Organic Chemistry, 85, 3497-3507. [Google Scholar] [CrossRef] [PubMed]
[15] Wu, Y.W., Xu, S.H., Wang, H., et al. (2021) Directing Group Enables Electrochemical Selectively Meta-Bromination of Pyridines under Mild Conditions. The Journal of Organic Chemistry, 86, 16144-16150. [Google Scholar] [CrossRef] [PubMed]
[16] Fu, N.K., Sauer, G.S. and Lin, S. (2017) Electrocatalytic Radical Dichlorination of Alkenes with Nucleophilic Chlorine Sources. Journal of the American Chemical Society, 139, 15548-15553. [Google Scholar] [CrossRef] [PubMed]
[17] Allen, B.D.W., Hareram, M.D., Seastram, A.C., et al. (2019) Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals. Organic Letters, 21, 9241-9246. [Google Scholar] [CrossRef] [PubMed]
[18] Zhou, Z.L., Yuan, Y., Cao, Y.M., et al. (2019) Synergy of Anodic Oxidation and Cathodic Reduction Leads to Electrochemical C-H Halogenation. Chinese Journal of Chemistry, 37, 611-615. [Google Scholar] [CrossRef
[19] Kim, K.S. and Kim, D.Y. (2022) Electrochemical Bromolactonization of Alkenoic Acids with Carbon Tetrabromide: Synthesis of Bromomethylated γ-Lactones. Synthetic Communications, 52, 402-412. [Google Scholar] [CrossRef
[20] Liang, Y.J., Jin, R., Jiao, N., et al. (2019) Efficient Electrocatalysis for the Preparation of (Hetero)aryl Chlorides and Vinyl Chloride with 1,2-Dichloroethane. Angewandte Chemie International Edition, 58, 4566-4570. [Google Scholar] [CrossRef] [PubMed]
[21] Liu, F., Wu, N. and Cheng, X. (2021) Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand. Organic Letters, 23, 3015-3020. [Google Scholar] [CrossRef] [PubMed]
[22] Dong, X.C., Roeckl, J.L., Waldvogel, S.R. and Morandi, B. (2021) Merging Shuttle Reactions and Paired Electrolysis for Reversible Vicinal Dihalogenations. Science, 371, 507-514. [Google Scholar] [CrossRef] [PubMed]