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Visible Light‐Mediated Metal‐Free Chlorodifluoromethylation of Arenes and Heteroarenes by a Hypervalent Iodine EDA Complex

Von Wiley-VCH zur Verfügung gestellt

A visible light-mediated electron donor–acceptor complex enabling direct chlorodifluoromethylation of (hetero)arenes is described. This method provides the privileged moiety with mild conditions across a broad range of functional groups and bioactive scaffolds. Post-functionalization reactions and key control experiments are reported as well. The core EDA complex is studied spectroscopically, enabling further synthetic applications in the future.


A novel EDA complex comprised of a bis(chlorodifluoroacetoxy)iodoarene and 1,3,5-trimethoxybenzene is described, which enables the direct radical C(sp2)−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 −CF2Cl moiety. Various mechanistic studies were performed to explore the EDA complex and radical generation pathway.

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