Photoredox-Catalyzed Synthesis of Remote Fluoroalkylated Azaarene Derivatives and the α-Deuterated Analogues via 1,n-Hydrogen-Atom-Transfer-Involving Radical Reactions.

A modular strategy to access the remote fluoroalkylated azaarene derivatives and the α-deuterated analogues, which are the isosteres of many pharmaceutically important compounds, is reported. Transformations under the sustainable photoredox catalysis platform could efficiently experience cascade radical addition, 1,n-hydrogen atom transfer (HAT), and single-electron reduction to offer the crucial anions α to azaarenes. Through reacting with H2O or the inexpensive D2O, two series of valuable products were obtained in high yields with substantial deuterium incorporation. The work demonstrates that the HAT of the α-sp3 C-H of the electron-withdrawing azaarenes with alkyl radicals is viable.