Prior to the modern era of cross-coupling, the nucleophilic substitution of arenes played a dominant role in the synthesis of substituted aromatics.  However, concerning the types of nucleophiles which can be added, substantial limitations exist.  Furthermore, very few catalytic strategies exist to facilitate this type of processes.  Thus, the field could substantially benefit from the development of new catalytic strategies for S<sub>N</sub>Ar reactions which might allow for broadened scope and more facile substitutions.  Herein, we present our efforts to develop an organocatalyst capable of facilitating the addition of nucleophiles to fluoroarenes, which do not ordinarily undergo substitution at any temperature, to substitute under relatively mild conditions.  We use this new form of catalysis to transform relatively inert C–F bonds into easily activated C–Cl bonds, allowing rapid use in other coupling strategies. This work further contributes to the growing number of selective C–F functionalization strategies available for use with highly fluorinated arenes.

New strategies for aromatic substitution; the development of S<sub>N</sub>Ar catalysis

253rd National Meeting (2017)

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New strategies for aromatic substitution; the development of SNAr catalysis

New strategies for aromatic substitution; the development of S_NAr catalysis