Visible Light‐Mediated Metal‐Free Chlorodifluoromethylation of Arenes and Heteroarenes by a Hypervalent Iodine EDA Complex
Daniel Lin, Vinayak Krishnamurti, G. K. Surya Prakash
Abstract
Abstract A novel EDA complex comprised of a bis(chlorodifluoroacetoxy)iodoarene and 1,3,5‐trimethoxybenzene is described, which enables the direct radical C(sp 2 )−H chlorodifluoromethylation of arenes and heteroarenes under monochromatic visible‐light irradiation. The procedure is mild, operationally simple, and utilizes commercially available reagents. The developed conditions demonstrate compatibility with a host of commonly encountered functionalities and biologically relevant scaffolds, whilst showcasing the post‐functionalization capabilities of the −CF 2 Cl moiety. Various mechanistic studies were performed to explore the EDA complex and radical generation pathway.
Topics & Concepts
ChemistryHypervalent moleculeMoietyReagentCombinatorial chemistryIodineSurface modificationVisible spectrumPhotochemistryOrganic chemistryOptoelectronicsPhysical chemistryPhysicsFluorine in Organic ChemistryRadical Photochemical ReactionsOxidative Organic Chemistry Reactions