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Visible Light‐Enhanced C−H Amination of Cyclic Ethers with Iminoiodinanes

Igor D. Jurberg, René A. Nome, Stefano Crespi, Teresa Dib Zambón Atvars, Burkhard König

2022Advanced Synthesis & Catalysis22 citationsDOIOpen Access PDF

Abstract

Abstract A two‐step protocol allowing the C−H amination of cyclic ethers with iminoiodinanes, followed by the reduction of the resulting intermediate has been developed for the preparation of amino alcohols. The initial C−H functionalization is accelerated by visible light, improving the reactivity compared to the thermal process performed in the dark. The effect of different substituents on the photochemical reactivity of iminoiodinanes has been studied both experimentally and computationally. Photophysical measurements and DFT calculations were performed to better understand the observed reactivities and corroborate the proposed mechanistic proposal. magnified image

Topics & Concepts

ChemistryAminationReactivity (psychology)Visible spectrumSurface modificationPhotochemistryCombinatorial chemistryOrganic chemistryCatalysisPhysical chemistryMedicinePathologyOptoelectronicsAlternative medicinePhysicsRadical Photochemical ReactionsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods