Dearomative (3+2) Cycloadditions between Indoles and Vinyldiazo Species Enabled by a Red‐Shifted Chromium Photocatalyst
Bradley K. Gall, Avery K. Smith, Eric M. Ferreira
Abstract
Abstract A direct dearomative photocatalyzed (3+2) cycloaddition between indoles and vinyldiazo reagents is described. The transformation is enabled by the development of a novel oxidizing Cr III photocatalyst, its specific reactivity attributed to increased absorptive properties over earlier Cr analogs and greater stability than Ru counterparts. A variety of fused indoline compounds are synthesized using this method, including densely functionalized ring systems that are feasible due to base‐free conditions. Experimental insights corroborate a cycloaddition initiated by nucleophilic attack at C3 of the indole radical cation by the vinyldiazo species.
Topics & Concepts
CycloadditionOxidizing agentChemistryNucleophileReagentChromiumIndole testCombinatorial chemistryReactivity (psychology)IndolinePhotocatalysisRing (chemistry)PhotochemistryMedicinal chemistryCatalysisOrganic chemistryPathologyAlternative medicineMedicineCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCyclopropane Reaction Mechanisms