Consecutive cross-dehydrogenative C–O and C–N construction for the synthesis of polyarene with AIE properties under electrochemical condition involving oxygen radical species

Abstract

A practical and scalable protocol for the regioselective C–H phenoxylation and azolation of phenol derivatives via consecutive electro-oxidative CDC reaction has been demonstrated. The reaction runs under metal-, oxidant- and reagent-free conditions, allowing for the efficient construction of a diaryl ether skeleton by the O-radical participating pathway and a subsequent electro-induced nucleophilic substitution (S_NAr) between azoles and in situ generated phenol derivatives. The electrolysis strategy provides a short-cut to form polyarenes with various fluorescence properties and is amenable to gram-scale synthesis in quantitative yield. Finally, a DFT calculation was performed for the mechanistic study.