碘和碘基试剂在脂肪族、芳香族和(异)环族体系硒化中的反应模式和机理方面的研究

IF 8.6 2区 化学 Q1 Chemistry Topics in Current Chemistry Pub Date : 2024-04-08 DOI:10.1007/s41061-024-00459-8
Pankaj Kumar, Aman Bhalla
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引用次数: 0

摘要

自生物活性化合物依布硒被发现以来,有机硒化合物一直是广泛研究的主题。最近,人们发现依布硒对 COVID-19 病毒的主要蛋白酶具有抑制作用。其他有机硒化合物也因其多种多样的生物活性而闻名,这些化合物还表现出与电子、材料和聚合物化学领域相关的有趣的物理特性。此外,由于硒有可能增强各种有机分子的生物活性,特别是与具有生物活性的杂环一起使用时,硒与这些分子的结合也引起了人们的极大关注。碘和碘基试剂在合成有机硒化合物的过程中发挥着重要作用,因其成本效益高、无毒、易于操作而备受重视。这些试剂能有效地硒化多种有机底物,包括烯烃、炔烃、环状分子、芳香分子和杂环分子。它们可用作催化剂、添加剂、诱导剂和氧化剂,促进在分子的不同位置引入不同的官能团,从而实现区域选择性和立体选择性方法。特定的碘试剂及其组合可以按照所需的反应途径进行定制。在此,我们全面回顾了过去十年中使用碘试剂对有机分子进行硒化反应的进展,重点介绍了反应模式、溶剂效应、加热、微波和超声条件。书中还详细讨论了机理方面的问题,如亲电、亲核、自由基、电化学以及通过硒化、多硒化和双官能化进行的扩环反应。综述还重点介绍了原位生成硒中间体所形成的各种环状、杂环和杂环烯,包括环酮、环醚、环内酯、硒酚、色酮、吡唑啉类、吡咯烷类、哌啶类、吲哚啉类、噁唑啉类、异噁唑啉类、内酯类、二氢呋喃类和异噁唑烷类。为了提高读者的阅读兴趣,本综述分为不同的章节,涵盖了脂肪族 sp2/sp 碳和环状 sp2 碳的硒化反应,然后又进一步细分为各种杂环分子。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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Reaction Pattern and Mechanistic Aspects of Iodine and Iodine-Based Reagents in Selenylation of Aliphatic, Aromatic, and (Hetero)Cyclic Systems

Organoselenium compounds have been the subject of extensive research since the discovery of the biologically active compound ebselen. Ebselen has recently been found to show activity against the main protease of the virus responsible for COVID-19. Other organoselenium compounds are also well-known for their diverse biological activities, with such compounds exhibiting interesting physical properties relevant to the fields of electronics, materials, and polymer chemistry. In addition, the incorporation of selenium into various organic molecules has garnered significant attention due to the potential of selenium to enhance the biological activity of these molecules, particularly in conjunction with bioactive heterocycles. Iodine and iodine-based reagents play a prominent role in the synthesis of organoselenium compounds, being valued for their cost-effectiveness, non-toxicity, and ease of handling. These reagents efficiently selenylate a broad range of organic substrates, encompassing alkenes, alkynes, and cyclic, aromatic, and heterocyclic molecules. They serve as catalysts, additives, inducers, and oxidizing agents, facilitating the introduction of different functional groups at alternate positions in the molecules, thereby allowing for regioselective and stereoselective approaches. Specific iodine reagents and their combinations can be tailored to follow the desired reaction pathways. Here, we present a comprehensive review of the progress in the selenylation of organic molecules using iodine reagents over the past decade, with a focus on reaction patterns, solvent effects, heating, microwave, and ultrasonic conditions. Detailed discussions on mechanistic aspects, such as electrophilic, nucleophilic, radical, electrochemical, and ring expansion reactions via selenylation, multiselenylation, and difunctionalization, are included. The review also highlights the formation of various cyclic, heterocyclic, and heteroarenes resulting from the in situ generation of selenium intermediates, encompassing cyclic ketones, cyclic ethers, cyclic lactones, selenophenes, chromones, pyrazolines, pyrrolidines, piperidines, indolines, oxazolines, isooxazolines, lactones, dihydrofurans, and isoxazolidines. To enhance the reader’s interest, the review is structured into different sections covering the selenylation of aliphatic sp2/sp carbon and cyclic sp2 carbon, and then is further subdivided into various heterocyclic molecules.

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来源期刊
Topics in Current Chemistry
Topics in Current Chemistry 化学-化学综合
CiteScore
11.70
自引率
1.20%
发文量
0
审稿时长
6-12 weeks
期刊介绍: Topics in Current Chemistry provides in-depth analyses and forward-thinking perspectives on the latest advancements in chemical research. This renowned journal encompasses various domains within chemical science and their intersections with biology, medicine, physics, and materials science. Each collection within the journal aims to offer a comprehensive understanding, accessible to both academic and industrial readers, of emerging research in an area that captivates a broader scientific community. In essence, Topics in Current Chemistry illuminates cutting-edge chemical research, fosters interdisciplinary collaboration, and facilitates knowledge-sharing among diverse scientific audiences.
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