The incorporation of fluorine based moieties into arene or heteroarene drug scaffolds can positively impact their pharmaceutical properties. As a consequence, much attention has been given to developing fluoronation methods which are cost-effective, operationally simple, and adaptable to large scale preparation. Here we report a robust state-of-the-art chlorodifluoromethylation method of arenes and heteroarenes mediated by visible light photosensitization. Chlorodifluoromethylacetic anhydride is applied here as a practical and widely available source of the reactive chlorodifluoromethyl radical. We then demonstrate the use of the chlorodifluoromethyl group as a functional handle for generating either aryl esters or difluoromethyl groups under one simple reaction manifold. <br/>

Radical chlorodifluoromethylation: Providing a versatile motif for (hetero)arene diversification

253rd National Meeting (2017)

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