Visible-Light Mediated Metal-Free 6π-Photocyclization of <i>N</i>-Acrylamides: Thioxanthone Triplet Energy Transfer Enables the Synthesis of 3,4-Dihydroquinolin-2-ones
Meghan J. Oddy, Daniel A. Kusza, Wade F. Petersen
Abstract
An efficient thioxanthone-catalyzed triplet energy transfer process for the synthesis of 3,4-dihydroquinolin-2-ones via a 6π-photocyclization is reported. Featuring a rare example of a metal-free formal C(sp2)–H/C(sp3)–H arylation mediated by visible-light, this work hopes to inspire further interest in these small molecules as sustainable alternatives to existing transition-metal photocatalysts in related processes.
Topics & Concepts
ThioxanthoneChemistryCombinatorial chemistryPhotochemistryEnergy transferVisible spectrumMoleculeOrganic chemistryChemical physicsOptoelectronicsMaterials sciencePolymerizationPolymerPhotopolymerRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods