ReportOrganic Chemistry

Hydrogenation of fluoroarenes: Direct access to all-cis-(multi)fluorinated cycloalkanes

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Science  10 Aug 2017:
DOI: 10.1126/science.aao0270

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All-cis-multifluorinated cycloalkanes exhibit intriguing electronic properties. In particular they display extremely high dipole moments perpendicular to the aliphatic ring, making them highly desired motifs in material science. Only very few such motifs have been prepared, with their syntheses requiring multistep sequences from diastereoselectively prefunctionalized precursors. Herein, we report a synthetic strategy to access these valuable materials via the rhodium-cyclic (alkyl)(amino)carbene (CAAC)-catalyzed hydrogenation of readily available fluorinated arenes in hexane. This route enables the scalable single-step preparation of a plethora of multisubstituted and multifluorinated cycloalkanes, including all-cis-1,2,3,4,5,6-hexafluorocyclohexane as well as cis-configured fluorinated aliphatic heterocycles.

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