Indoles and benzofurans are important biologically relevant compounds, and in recent decades fluorinated compounds have become increasingly prevalent among newly approved pharmaceuticals.  Variously substituted fluorinated indoles and benzofurans have been synthesized in one-pot from aniline and phenol derived starting materials.  This new method makes use of an oxidative dearomatization enabled coupling with hexafluoroacetylacetone followed by cyclization and dehydration.  Transformations of the trifluoroacetyl group at the C-3 position have been explored and the unique versatility of this functionality has been leveraged towards the pursuit of pharmaceutical compounds.

Novel synthesis of fluorinated indoles and benzofurans via oxidative dearomatization

253rd National Meeting (2017)

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