DDQ-Mediated Three-Component Dioxygenation of Alkenes

A new DDQ-mediated three-component dioxygenation of alkenes has been established, providing a direct and metal-free access toward densely functionalized 4,5-dichloro-3-hydroxyphthalonitrile derivatives with generally good to excellent yields under mild conditions. During this process, DDQ plays dual roles as both a dehydrogenation reagent and a coupling partner, enabling oxidative coupling to form two C–O functionalities in a highly atom-economy fashion.本研究建立了一种由2,3-二氯-5,6-二氰基对苯醌（DDQ）介导的烯烃三组分双氧化新反应，可在温和条件下以普遍良好至优异的收率，直接且无金属地获得高度官能化的4,5-二氯-3-羟基邻苯二甲腈衍生物。在此反应过程中，DDQ同时兼具脱氢试剂与偶联底物的双重作用，可通过氧化偶联以高原子经济性的方式构建两个C-O官能团。