Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability

Herein, we report chemoselective trifluoroethylation routes of unmasked 2-arylquinazolin-4­(3H)-ones using mesityl­(2,2,2-trifluoroethyl)­iodonium triflate at room temperature. Homologous C-, O-, and N-functionalized subclasses are accessed in a straightforward manner with a wide substrate scope. These chemoselective branching events are driven by Pd-catalyzed ortho-selective C–H activation at the pendant aryl ring and base-promoted reactivity modulation of the amide group, leveraging the intrinsic directing capability and competing pronucleophilicity of the quinazolin-4­(3H)-one framework. Furthermore, outstanding photostability of the quinazolin-4­(3H)-one family associated with nonradiative decay is presented.本文报道了以均三甲苯基(2,2,2-三氟乙基)三氟甲磺酸碘鎓盐为试剂，在室温条件下实现未保护2-芳基喹唑啉-4(3H)-酮（2-arylquinazolin-4(3H)-ones）的化学选择性三氟乙基化反应路径。该反应可通过简便策略获得C、O、N位官能化的同源产物子类，且底物适用范围广泛。这类化学选择性分支反应的核心驱动机制为：钯催化侧连芳环的邻位选择性C-H活化，以及碱促进的酰胺基团反应性调控，同时借助了喹唑啉-4(3H)-酮骨架固有的导向能力与竞争性亲核性。此外，本文还展示了喹唑啉-4(3H)-酮类化合物优异的光稳定性，该特性与其分子的无辐射衰减过程相关。