American Chemical Society
ol501997n_si_001.pdf (13.6 MB)

Synthesis of Polyfluoroalkyl Aza-Polycyclic Aromatic Hydrocarbons Enabled by Addition of Perfluoroalkyl Radicals onto Vinyl Azides

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journal contribution
posted on 2014-08-15, 00:00 authored by Yi-Feng Wang, Geoffroy Hervé Lonca, Maïwenn Le Runigo, Shunsuke Chiba
Radical perfluoroalkylation of α-(biaryl-2-yl)­vinyl azides is capable of supplying polyfluoroalkyl aza-polycyclic aromatic hydrocarbons (aza-PAHs). Commercially available Me3SiRf (Rf = CF3, C2F5, and C3F7) are employed as the sources of perfluoroalkyl radicals upon oxidation with PhI­(OAc)2. The addition of perfluoroalkyl radicals to biarylvinyl azides generates the corresponding iminyl radicals, which subsequently cyclize with the intramolecular arene moiety, furnishing aza-PAH skeletons having polyfluoroalkyl (RfCH2) function.