Oxidative Dearomative Coupling of Electron-Deficient Arenols Using Hypohalite Catalysis.

We developed performant in situ hypohalite, especially hypobromite, catalysis for the oxidative dearomatization of low-reactivity electron-deficient arenols. The reaction scope encompasses inter- and intramolecular oxidative dearomative C-O, C-N, and C-C coupling reactions. Notably, using a chiral ammonium countercation, we achieved enantioselective hypobromite catalysis for oxidative dearomative coupling reactions. Mechanistic studies revealed that the reaction mechanisms might differ depending on the halide identity.