二甲亚砜作为甲基化试剂在有机合成中的应用
收稿日期: 2022-11-23
修回日期: 2023-01-31
网络出版日期: 2023-03-07
基金资助
山西省高等学校科技创新项目基金(2021L081)
Application of Dimethyl Sulfoxide as Methylating Reagent in Organic Synthesis
Received date: 2022-11-23
Revised date: 2023-01-31
Online published: 2023-03-07
Supported by
Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi Province(2021L081)
在药物分子中引入甲基可改变其药代动力学特性与药理特性, 这种“神奇的甲基效应”使得甲基化成为有机合成与药物化学领域十分重要的一类反应. 近年来, 过渡金属催化的偶联反应以及光或电促进的有机反应成为甲基化反应的新策略, 并相继开发了系列廉价易得、低毒高效、适用性广的甲基化试剂. 其中, 二甲亚砜(DMSO)作为一种来源广泛、性能优良的溶剂与多功能反应试剂, 受到研究者们越来越多的关注. 基于此, 聚焦交叉偶联反应与自由基反应, 系统阐述DMSO/DMSO-d6作为甲基化/三氘甲基化试剂在有机合成中的应用, 并探讨相关的反应机理、发展趋势以及合成过程所面临的挑战.
关键词： 二甲亚砜(DMSO); 氘代二甲亚砜; 甲基化; 三氘甲基化; 自由基反应
田钰 , 张娟 , 高文超 , 常宏宏 . 二甲亚砜作为甲基化试剂在有机合成中的应用[J]. 有机化学, 2023 , 43(7) : 2391 -2406 . DOI: 10.6023/cjoc202211026
The introduction of methyl groups into drug molecules can change their pharmacokinetic and pharmacological properties. This “magical methyl effectˮ makes methylation a very important reaction in the field of organic synthesis and pharmaceutical chemistry. In recent years, the transition metal-catalyzed coupling reaction and the organic reaction promoted by light or electricity have become the new strategies for methylation reaction. A series of cheap, low toxicity, high efficiency and wide applicability of methylating reagents have been developed. Among them, dimethyl sulfoxide (DMSO), as a kind of solvent with wide sources, excellent performance and multi-functional reagent, has been paid more and more attention by researchers. Based on this, by focusing on the cross-coupling reaction and free radical reaction, the application of DMSO/ DMSO-d6 as methylation/trideuterium methylating reagent in organic synthesis is systematically described, and the relevant reaction mechanism, development trend and challenges in the synthesis process are discussed.
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