In our efforts to synthesize large fluorinated polyarene scaffolds we require tera- and hexafluoronaphthalene derivatives as building blocks.  These compounds are not readily available and we developed two approaches to these important intermediates:(1) A series of fluorinated benzofused enediynes, obtained through Sonogashira cross-coupling, was subjected to Bergman cyclization, furnishing a variety of di- and tetrafluorinated naphthalene derivatives.  We will present selected structures of starting materials and cyclized products to discuss their molecular structures and packing arrangements.(2) A second route relies on the Diels-Alder reaction of fluorinated thiophenes with tetrafluorobenzye.  We will present our results on the synthesis of novel fluorinated 3,4-disubstituted thiophene derivatives and their cycloaddition to tetrafluorobenzyne, providing access to tetra- and hexafluoronaphthalene derivatives.

Syntheses of highly fluorinated naphthalene derivatives: Comparison of the Bergman cyclization approach with a fluorothiophene route

243rd National Meeting (2012)

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