Metal‐Free Photoredox‐Catalyzed Hydrodefluorination of Fluoroarenes Utilizing Amide Solvent as Reductant
Naoyuki Toriumi, Kazuya Yamashita, Nobuharu Iwasawa
Abstract
A metal-free photoredox-catalyzed hydrodefluorination of fluoroarenes was achieved by using N,N,N',N'-tetramethyl-para-phenylenediamine (1) as a strong photoreduction catalyst. This reaction was applicable not only to electron-rich monofluoroarenes but also to polyfluoroarenes to afford non-fluorinated arenes. The experimental mechanistic studies indicated that the amide solvent NMP plays an important role for regeneration of the photocatalyst, enabling additive-free photoreduction catalysis.
Topics & Concepts
ChemistryCatalysisAmidePhotoredox catalysisPhotocatalysisPhotochemistrySolventMetalOrganic chemistryFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques