Visible- and UV-Light-Induced Decarboxylative Radical Reactions of Benzoic Acids Using Organic Photoredox Catalysts
Suzuka Kubosaki, Haruka Takeuchi, Yutaka Iwata, Yosuke Tanaka, Kazuyuki Osaka, Mugen Yamawaki, Toshio Morita, Yasuharu Yoshimi
Abstract
Photoinduced decarboxylative radical reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions and mild heating afforded adducts, arylboronate esters, and the reduction product, respectively. The reaction is thought to involve single-electron transfer promoted the generation of aryl radicals via decarboxylation. A diverse range of benzoic acids were found to be suitable substrates for this photoreaction. Only our two-molecule organic photoredox system can work well for the direct photoinduced decarboxylation of benzoic acids.
Topics & Concepts
DecarboxylationChemistryPhotochemistryPhotoredox catalysisRadicalCatalysisBenzoic acidAcetonitrileOrganic chemistryPhotocatalysisRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods