Triphenylphosphine oxide promoting visible-light-driven C–C coupling <i>via</i> desulfurization
Shea Stewart, Robert Maloney, Yugang Sun
Abstract
Triphenylphosphine oxide (TPPO) and triphenylphosphine (TPP) can form a complex in solution, promoting visible light absorption to trigger electron transfer within the complex and generate radicals. Subsequent radical reactions with thiols enable desulfurization to produce carbon radicals that react with aryl alkenes to yield new C-C bonds. Since ambient oxygen can easily oxidize TPP to TPPO, the reported method requires no explicit addition of a photocatalyst. This work highlights the promise of using TPPO as a catalytic photo-redox mediator in organic synthesis.
Topics & Concepts
TriphenylphosphineTriphenylphosphine oxideFlue-gas desulfurizationPhotochemistryChemistryVisible spectrumOxideAbsorption (acoustics)RadicalCoupling (piping)Electron transferMaterials scienceOrganic chemistryCatalysisOptoelectronicsMetallurgyComposite materialSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsAsymmetric Hydrogenation and Catalysis