Recent years have witnessed burgeoning interest in metal promoted  fluorination and trifluoromethylation of arenes due to unique properties  of fluorinated aromatic compounds in medicinal chemistry and material  science. However to date most of the reported strategies require  pre-functionalized arenes and have shown limited generality. In order to  address this limitation, we became interested in utilizing multi-ynes  to generate aromatic fluorides. We found that the treatment of multi-yne  substrates with various nucleophilic fluorinating reagents in the  presence catalytic amounts of silver salts afforded aryl fluorides  almost quantitatively with high level of regeoselectivity. Initial study  on the reaction scope showed that various functional groups containing  oxygen and nitrogen heteroatoms are compatible with this fluorination.  The success of this fluorination reaction suggests a potentially general  strategy to synthesize aromatic fluorides from non-aromatic building  blocks under mild conditions. Ongoing efforts to expand the reaction  scope and to probe the detailed reaction mechanism will be presented.

Metal-catalyzed formation of fluorinated arenes from multi-ynes

244th National Meeting (2012)

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