The Journal of Organic Chemistry · 2014 · 96 citations · 71 references
Natural SciencesChemical EngineeringChemistryCatalysisInorganic ChemistryOrganic ChemistryCatalytic MaterialsCatalytic MechanismsCatalytic Reaction KineticsHeterocyclic ChemistryMetal CatalysisOrganic SynthesisCatalytic Reaction MechanismsHeterocycle FunctionalizationMetal-based CatalysisMetal-mediated CyclizationMild Reaction ConditionsNoble Metal CatalysisRadical MechanismsTransition-metal-catalyzed Functionalization
Silver-catalyzed C(sp(2))-H functionalization/C-O cyclization has been developed. The scalable reaction proceeds at room temperature in an open flask. The present method exhibits good functional-group compatibility because of the mild reaction conditions. Using a AgNO3 catalyst and a (NH4)2S2O8 oxidant in CH2Cl2/H2O solvent, various lactones are obtained in good to excellent yields. A kinetic isotope effect (KIE) study indicates that the reaction may occur via a radical process.
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