Visible‐light‐mediated Synthesis of Bromo‐containing Azaspirotrienediones from <i>N</i>‐phenylpropynamides
Yuan Chen, Fo‐Yun Lu, Rui‐Xue Li, Zhi Guan, Yan‐Hong He
Abstract
Abstract A visible‐light‐mediated reaction of N ‐phenylpropynamides with diethyl 2,2‐dibromomalonate for the synthesis of bromo‐substituted azaspirotrienediones has been developed. This method allows the formation of C−Br, C−C and C=O bonds in one pot via a cascade radical addition/ipso‐cyclization/oxidation process. A possible radical mechanism involving single electron transfer and energy transfer processes is proposed based on control experiments, cyclic voltammetry determination and Stern‐Volmer quenching experiments.
Topics & Concepts
ChemistryQuenching (fluorescence)Electron transferPhotochemistryCyclic voltammetryEnergy transferVisible spectrumCascadeRadicalCombinatorial chemistryElectrochemistryOrganic chemistryPhysical chemistryFluorescenceChemical physicsChromatographyElectrodeQuantum mechanicsOptoelectronicsPhysicsRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods