Electrochemical C-H Functionalization of (Hetero)Arenes-Optimized by DoE.,Chemistry - A European Journal

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Electrochemical C-H Functionalization of (Hetero)Arenes-Optimized by DoE.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-03-30 , DOI: 10.1002/chem.202001171
Maurice Dörr ₁ , Johannes L Röckl _{1,

2} , Jonas Rein ₁ , Dieter Schollmeyer ₁ , Siegfried R Waldvogel _{1,

2}

Affiliation

A novel approach towards the activation of different arenes and purines including caffeine and theophylline is presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron‐doped diamond (BDD) electrodes. Good yields up to 59 % were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized using Design of Experiment (DoE) techniques giving a detailed insight to the significance of the reaction parameters. The mechanism was investigated by cyclic voltammetry (CV). Subsequent transition metal‐catalyzed as well as metal‐free functionalization led to interesting motifs in excellent yields up to 94 %.

中文翻译：

通过DoE优化（杂）戊烯的电化学CH功能化。

提出了一种新的方法来激活包括咖啡因和茶碱在内的不同的芳烃和嘌呤。1,1,1,1,3,3,3-六氟异丙醇（HFIP）芳基醚的简单，安全和可扩展的电化学合成是使用带有硼掺杂金刚石（BDD）电极的简易电解装置进行的。获得了高达59％的高产率。三乙胺被用作碱，因为它与HFIP形成高导电性介质，从而使多余的辅助电解质成为多余。使用实验设计（DoE）技术优化了合成，从而深入了解了反应参数的重要性。通过循环伏安法（CV）研究了该机理。随后的过渡金属催化以及无金属官能化导致有趣的图案，产率高达94％。

更新日期：2020-03-30

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