The influence of C–F⋯H–X hydrogen-bonding interactions on the reactivity and selectivity of organic reactions

IF 39 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Pengwei Xu, Xin Wang, Tao Wang, Zhong-Yan Cao, Jin-Sheng Yu, Jian Zhou
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引用次数: 0

Abstract

Hydrogen-bonding interactions are ubiquitous in biological and chemical systems. Nevertheless, whether fluorine bonded to carbon (C–F bond) can act as a hydrogen bond (H-bond) acceptor has been debated for decades. Evidence accumulated to date supports the existence of C–F⋯H–X interactions, and uncovering such non-classical interactions can greatly influence the reactivity and selectivity of organic reactions. Notably, the focus has shifted from applying such interactions to explaining the observed fluorine effects of organic reactions, to harness it for rational design of new reagents and catalysts for precise synthesis. This review will summarize the advances in understanding the impact of C–F⋯H–X interactions on organic reactions, and cast light on its future applications in organic synthesis.

Abstract Image

C-F⋯H-X氢键相互作用对有机反应活性和选择性的影响
氢键相互作用在生物和化学系统中无处不在。然而,氟与碳键(C-F键)是否可以作为氢键(h键)受体一直争论了几十年。迄今为止积累的证据支持C-F⋯H-X相互作用的存在,发现这种非经典相互作用可以极大地影响有机反应的反应性和选择性。值得注意的是,重点已经从应用这种相互作用转移到解释观察到的有机反应的氟效应,利用它来合理设计用于精确合成的新试剂和催化剂。本文将总结C-F⋯H-X相互作用对有机反应影响的研究进展,并展望其在有机合成中的未来应用。
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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