DDQ-mediated three-component dioxygenation of alkenes

Tian-Shu Zhang, Yan-Jie Xiong, Wen-Juan Hao, Xiao-Tong Zhu, Shu-Liang Wang,* Guigen Li, Shu-Jiang Tu,* Bo Jiang*

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

J. Org. Chem. 2016, 81, 9350-9355