六氟磷酸盐
化学
氢同位素
氢键
动力学同位素效应
三键
氢
有机化学
离子液体
氘
催化作用
分子
双键
物理
量子力学
作者
Yang Ni,Jonathan Lebelt,Milena Barp,Florian Kreuter,Jiaye Jin,H. Buttkus,Martin Kretzschmar,Ralf Tonner,Knut R. Asmis,Tanja Gulder
标识
DOI:10.1002/ange.202417889
摘要
There is a perpetual need for efficient and mild methods to integrate deuterium atoms into carbon frameworks through late‐stage modifications. We have developed a simple and highly effective synthetic route for hydrogen isotope exchange (HIE) in aromatic compounds under ambient conditions. This method utilizes catalytic amounts of hexafluorophosphate (PF6−) in deuterated 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP‐d1) and D2O. Phenols, anilines, anisoles, and heterocyclic compounds were converted with high yields and excellent deuterium incorporations, which allows for the synthesis of a wide range of deuterated aromatic compounds. Spectroscopic and theoretical studies show that an interactive H‐bonding network triggered by HFIP‐d1 activates the typically inert P‐F bond in PF6‐ for D2O addition. The thus in‐situ formed DPO2F2 triggers then HIE, offering a new way to deuterated building blocks, drugs, and natural‐product derivatives with high deuterium incorporation via the activation of strong bonds.
科研通智能强力驱动
Strongly Powered by AbleSci AI