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深入探讨 DMSO 与过氧化物在有机合成中的协同关系。

A Comprehensive Exploration of the Synergistic Relationship between DMSO and Peroxide in Organic Synthesis.

机构信息

Department of Chemistry, School of Advanced Sciences, VIT, Vellore, 632014, Tamil Nadu, India.

Department of Chemistry, Central Tribal University of Andhra Pradesh, Kondakarakam Village, Cantonment, Vizianagaram, Andhra Pradesh, 535003, India.

出版信息

Top Curr Chem (Cham). 2024 Nov 15;382(4):36. doi: 10.1007/s41061-024-00482-9.

DOI:10.1007/s41061-024-00482-9
PMID:39548041
Abstract

In the realm of organic synthesis, reagents can serve not only as solvents but also as synthons. Dimethyl sulfoxide (DMSO) is recognized for its efficiency in this dual capacity, enabling diverse chemical transformations. DMSO can generate various synthons, including methyl, methylene, methine, oxygen, and methyl sulfoxide, broadening the accessible compound repertoire. Activation of DMSO as a reagent relies heavily on synergies with secondary agents like peroxide, persulfate, or iodine. Recent years have witnessed a surge in innovative synthetic techniques harnessing the synergistic interplay of DMSO and peroxide, leading to environmentally friendly and cost-effective reactions with mild conditions. This review highlights the synergistic effects of DMSO and peroxides (up to 2023), detailing their activation mechanisms and the generation of various synthons, along with numerous reported derivatives. Although this topic has received considerable attention in recent years, there are numerous discrepancies and a plethora of possibilities yet to be explored. We anticipate that this review will significantly support researchers in advancing their innovations to a greater extent in the future.

摘要

在有机合成领域,试剂不仅可以充当溶剂,还可以作为合成子。二甲基亚砜(DMSO)因其在这两种功能上的高效性而备受认可,能够实现多种化学转化。DMSO 可以生成各种合成子,包括甲基、亚甲基、次甲基、氧和甲基亚砜,从而拓宽了可利用的化合物范围。DMSO 作为试剂的激活主要依赖于与过氧化物、过硫酸盐或碘等辅助试剂的协同作用。近年来,利用 DMSO 和过氧化物协同作用的创新合成技术呈爆发式增长,这些技术可实现温和条件下绿色环保且具有成本效益的反应。本综述重点介绍了 DMSO 和过氧化物(截至 2023 年)的协同效应,详细阐述了它们的激活机制和各种合成子的生成,以及大量报道的衍生物。尽管近年来该主题受到了广泛关注,但仍存在许多差异和大量尚未探索的可能性。我们预计,本综述将在未来更大程度上支持研究人员推进他们的创新。

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本文引用的文献

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Iodine and ammonium persulfate mediated activation of DMSO: an approach to -formylation of amides and synthesis of isatins.碘和过硫酸铵介导的 DMSO 活化:一种酰胺 - 甲酰化和异吲哚啉酮合成的方法。
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Regioselective Synthetic Approach to Higher Alkenes from Lower Alkenes with Sulfoxides in the Fe/HO System Direct Alkylation or Arylation of the Csp-H Bond on the C═C Bond of Alkenes.在铁/羟基体系中利用亚砜从低级烯烃合成高级烯烃的区域选择性方法 烯烃碳碳双键上Csp-H键的直接烷基化或芳基化
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[3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO.
基于 DMSO 作为非相邻双亚甲合成子的喹啉分子中吡啶结构的[3+1+1+1]环化反应:由芳醛、芳胺和 DMSO 简单合成 3-芳基喹啉。
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Potassium Persulfate Mediated Chemodivergent C-3 Functionalization of 2-Indazoles with DMSO as C Source.过硫酸钾介导的 2-吲哚与 DMSO 作为 C 源的化学发散性 C-3 官能团化。
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Iodine-Mediated Oxidative Rearrangement of α,β-Unsaturated Diaryl Ketones: A Facile Access to 1,2-Diaryl Diketones.碘介导的α,β-不饱和二芳基酮的氧化重排:一种简便合成1,2-二芳基二酮的方法。
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Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon.无过渡金属条件下利用二甲基亚砜合成喹唑啉酮。
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A cascade oxidation/[4 + 1] annulation of sulfonium salts for synthesis of polyfunctional furans: DMSO as one carbon source.用于合成多官能团呋喃的锍盐级联氧化/[4 + 1]环化反应:以二甲基亚砜作为一个碳源
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TFA-Mediated DMSO-Participant Sequential Oxidation/1,3-Dipolar Cycloaddition Cascade of Pyridinium Ylides for the Assembly of Indolizines.三氟乙酸介导的吡啶叶立德的二甲基亚砜-参与的顺序氧化/1,3-偶极环加成串联反应用于中氮茚的组装。
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