Pletz Jakob, Koeberl Christoph, Fuchs Michael, Steiner Oliver, Goessler Walter, Kroutil Wolfgang
Institute of Chemistry NAWI Graz BioTechMed Graz University of Graz Heinrichstraße 28 8010 Graz Austria.
Institute of Chemistry NAWI Graz University of Graz Universitätsplatz 1/1 8010 Graz Austria.
European J Org Chem. 2019 Jan 31;2019(4):682-690. doi: 10.1002/ejoc.201801111. Epub 2018 Oct 8.
Fluorination and trifluoromethylation are indispensable tools in the preparation of modern pharmaceuticals and APIs. Herein we present a concept for the introduction of a trifluoromethyl group into unprotected phenols employing catalytic copper(I) iodide and hydroquinone, BuOOH, and the Langlois' reagent. The method proceeds under mild conditions and exhibits an extended substrate scope compared to the biocatalytic trifluoromethylation using laccase from . Various functional groups such as aldehydes, esters, ethers, ketones and nitriles were tolerated. The hydroquinone-mediated trifluoromethylation reaction allowed accessing trifluoromethylated phenols, which are cumbersome to prepare via previously known chemical methods.
氟化和三氟甲基化是现代药物和活性药物成分制备中不可或缺的工具。在此，我们提出了一种利用催化碘化亚铜、对苯二酚、叔丁基过氧化氢和朗格卢瓦试剂将三氟甲基引入未保护酚类的概念。该方法在温和条件下进行，与使用来自[具体来源未给出]的漆酶进行的生物催化三氟甲基化相比，底物范围有所扩大。醛、酯、醚、酮和腈等各种官能团都能耐受。对苯二酚介导的三氟甲基化反应能够得到通过先前已知化学方法难以制备的三氟甲基化酚类。
