1,3-Oxyalkynylation of Aryl Cyclopropanes with Ethylnylbenziodoxolones Using Photoredox Catalysis
Zhijun Zuo, Armido Studer
Abstract
Alkynes and cyclopropanes are vital motifs in chemistry. Herein, a photoredox catalyzed 1,3-oxyalkynylation of aryl cyclopropanes with ethylnylbenziodoxolones (EBXs) in an atom-economic fashion is described. This cascade comprises single-electron oxidation of the aryl cyclopropane and nucleophilic ring opening followed by radical alkynylation at the benzylic position. The EBX compounds act as bifunctional reagents providing the nucleophilic acid as well as the alkynyl entity. The introduced method features mild conditions and wide substrate scope.
Topics & Concepts
ChemistryCyclopropaneArylNucleophilePhotoredox catalysisBifunctionalRing (chemistry)CatalysisCombinatorial chemistryAlkynylationNucleophilic additionReagentAcid catalysisStereochemistryOrganic chemistryPhotocatalysisAlkylCyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods