Intermolecular 1,2-difunctionalization of alkenes

IF 39 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Yuanrui Wang, Zhi-Peng Bao, Xu-Dong Mao, Ming Hou, Xiao-Feng Wu
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Abstract

Alkenes are an important class of organic compounds with a carbon–carbon double bond and a wide range of industrial and natural sources. The presence of π bonds provides the possibility for many forms of transformations. The direct difunctionalization of olefins can continuously introduce two identical or different groups into the olefin molecule at one time, while achieving a rapid increase in molecular complexity, and it also gives the organic compound potential or specific application value. In general, olefin difunctionalization can be achieved via three different reaction modes. Firstly, metal species can add double bonds by employing transition metals; further coupling can then be followed to complete the difunctionalization. Another intriguing approach is that radicals add to the olefins and then are quenched in diverse ways. The ability to continuously introduce diverse functional groups is the most significant feature of this platform. The third mode is that the olefin is transformed into a cationic radical or anionic radical intermediate through single-electron transfer. This strategy is less developed and more novel, but has certain limitations. Driven by the innovation of synthetic chemistry strategies, the difunctionalization of olefins, which was previously difficult to achieve, has also been gradually achieved. This review updates the latest progress in the 1,2-difunctionalization of olefins in the past five years. We aim to classify reaction mechanisms and functional group types. It should be stated that reactions with olefin double bonds to form rings are not included here.

Abstract Image

烯烃分子间1,2-二官能化
烯烃是一类重要的碳碳双键有机化合物,具有广泛的工业和天然来源。π键的存在为多种形式的转化提供了可能性。烯烃直接双官能化可以在烯烃分子中同时连续引入两个相同或不同的基团,同时实现分子复杂性的快速增加,也赋予了有机化合物潜在的或特定的应用价值。一般来说,烯烃的双官能化可以通过三种不同的反应方式来实现。首先,金属可以通过过渡金属加入双键;然后可以遵循进一步的耦合来完成非功能化。另一种有趣的方法是,自由基加入烯烃,然后以不同的方式被淬灭。不断引入不同功能组的能力是该平台最重要的特性。第三种模式是烯烃通过单电子转移转化为阳离子自由基或阴离子自由基中间体。这一策略尚不成熟,也比较新颖,但也有一定的局限性。在合成化学策略创新的推动下,以前难以实现的烯烃双官能化也逐步实现。本文综述了近五年来烯烃1,2-双官能化的最新进展。我们的目标是对反应机理和官能团类型进行分类。应当说明的是,这里不包括用烯烃双键形成环的反应。
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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来源期刊
Chemical Society Reviews
Chemical Society Reviews 化学-化学综合
CiteScore
80.80
自引率
1.10%
发文量
345
审稿时长
6.0 months
期刊介绍: Chemical Society Reviews is published by: Royal Society of Chemistry. Focus: Review articles on topics of current interest in chemistry; Predecessors: Quarterly Reviews, Chemical Society (1947–1971); Current title: Since 1971; Impact factor: 60.615 (2021); Themed issues: Occasional themed issues on new and emerging areas of research in the chemical sciences
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