Click and Bio-Orthogonal Reactions with Mesoionic Compounds,Chemical Reviews

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Click and Bio-Orthogonal Reactions with Mesoionic Compounds
Chemical Reviews ( IF 51.4 ) Pub Date : 2020-11-25 , DOI: 10.1021/acs.chemrev.0c00806
Karine Porte ₁ , Margaux Riomet ₁ , Carlotta Figliola ₁ , Davide Audisio ₁ , Frédéric Taran ₁

Affiliation

Click and bio-orthogonal reactions are dominated by cycloaddition reactions in general and 1,3-dipolar cycloadditions in particular. Among the dipoles routinely used for click chemistry, azides, nitrones, isonitriles, and nitrile oxides are the most popular. This review is focused on the emerging click chemistry that uses mesoionic compounds as dipole partners. Mesoionics are a very old family of molecules, but their use as reactants for click and bio-orthogonal chemistry is quite recent. The facility to derivatize these dipoles and to tune their reactivity toward cycloaddition reactions makes mesoionics an attractive opportunity for future click chemistry development. In addition, some compounds from this family are able to undergo click-and-release reactions, finding interesting applications in cells, as well as in animals. This review covers the synthetic access to main mesoionics, their reaction with dipolarophiles, and recent applications in chemical biology and heterocycle synthesis.

中文翻译：

与介离子化合物的点击和生物正交反应

点击和生物正交反应通常以环加成反应为主，特别是 1,3-偶极环加成反应。在通常用于点击化学的偶极子中，叠氮化物、硝酮、异腈和腈氧化物是最受欢迎的。这篇综述的重点是新兴的点击化学，它使用介离子化合物作为偶极子伙伴。Mesoionics 是一个非常古老的分子家族，但它们作为点击和生物正交化学反应物的使用是最近的事情。衍生这些偶极子并调整它们对环加成反应的反应性的设施使介离子成为未来点击化学发展的一个有吸引力的机会。此外，该家族中的一些化合物能够进行点击释放反应，在细胞和动物中发现了有趣的应用。

更新日期：2020-11-25

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