Pd(0)/Blue Light Promoted Carboiodination Reaction – Evidence for Reversible C–I Bond Formation via a Radical Pathway
Austin D. Marchese, Andrew G. Durant, Cian M. Reid, Clara Jans, Ramon Arora, Mark Lautens
Abstract
A Pd(0)/blue light catalyzed carboiodination reaction is reported. A simple, air-stable catalytic system, utilizing [Pd(allyl)Cl]2 and DPEPhos, generated a variety of iodinated hetero- and carbocycles including oxindoles, dihydrobenzofurans, indolines, a chromane, and a tetrahydronaphthalene. This protocol was tolerant of sensitive functional groups including free carboxylic acids, phenols, and anilines, as well as pyridines, while delivering products in up to 94% yield. Support for a reversible C–I bond formation via a single electron mechanism was obtained using a deuterium labeled substrate and a stoichiometric neopentylpalladium species.
Topics & Concepts
ChemistryYield (engineering)StoichiometryCatalysisSubstrate (aquarium)PhotochemistryMedicinal chemistryReaction mechanismDeuteriumPhenolsCombinatorial chemistryOrganic chemistryMaterials scienceQuantum mechanicsPhysicsOceanographyMetallurgyGeologyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions