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 alpha-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 a 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 alpha-sp(3) C-H of the electron-withdrawing azaarenes with alkyl radicals is viable.

Automated summary

A modular strategy was reported for accessing remote fluoroalkylated azaarene derivatives and alpha-deuterated analogues, isosteres of many pharmaceutically important compounds. Transformations under sustainable photoredox catalysis platform efficiently yielded valuable products with high yields and substantial deuterium incorporation. The work demonstrated the viability of hydrogen atom transfer of the alpha-sp(3) C-H of electron-withdrawing azaarenes with alkyl radicals.