Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes
Sourav Roy, Gourav Kumar, Indranil Chatterjee
Abstract
A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.
Topics & Concepts
DiazoChemistryCycloadditionReactivity (psychology)CarbeneCatalysisIn situPhotochemistryCombinatorial chemistryVisible spectrumOxygenOrganic chemistryAlternative medicineOptoelectronicsMedicinePathologyPhysicsCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods