Elumalai Vijayaragavan, Hansen Jørn H
UiT The Arctic University of Norway, Department of Chemistry, Chemical Synthesis and Analysis Group N9037 Tromsø Norway
RSC Adv. 2020 Nov 7;10(66):40582-40587. doi: 10.1039/d0ra08580d. eCollection 2020 Nov 2.
A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols -hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and HO/HBr as the reagent under unprecedentedly simple and convenient conditions. A wide range of arylboronic acids were smoothly transformed into substituted phenols in very good to excellent yields without chromatographic purification. The reaction is scalable up to at least 5 grams at room temperature with one-minute reaction time and can be combined in a one-pot sequence with bromination and Pd-catalyzed cross-coupling to generate more diverse, highly substituted phenols.
开发了一种温和、绿色且高效的方法用于合成取代酚——在乙醇中进行芳基硼酸的羟基化反应。该方法在前所未有的简单便捷条件下，利用过氧化氢水溶液作为氧化剂，HO/HBr作为试剂。多种芳基硼酸能顺利转化为取代酚，产率良好至优异，无需柱色谱纯化。该反应在室温下反应一分钟，放大至至少5克规模时仍可顺利进行，并且可以与溴化反应和钯催化的交叉偶联一锅法结合，生成更多样化、高度取代的酚。
