Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Graduate School Materials Science in Mainz, Staudingerweg 9, 55128, Mainz, Germany.
Chemistry. 2020 Aug 12;26(45):10195-10198. doi: 10.1002/chem.202001171. Epub 2020 Jun 29.
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 %.
提出了一种新颖的方法，用于激活不同芳基和嘌呤，包括咖啡因和茶碱。使用带有掺硼金刚石（BDD）电极的简单电解装置进行了简单、安全且可扩展的电化学合成 1,1,1,3,3,3-六氟异丙醇（HFIP）芳基醚。获得了高达 59%的良好产率。使用三乙胺作为碱，因为它与 HFIP 形成了高导电性的介质，使得不需要额外的支持电解质。通过实验设计（DoE）技术对合成进行了优化，详细了解了反应参数的重要性。通过循环伏安法（CV）研究了该机制。随后的过渡金属催化和无金属官能化导致了高达 94%的优异产率的有趣主题。
