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• W3080737942 abstract "Abstract The strong and unreactive C−F bond makes polyfluorocarbons extremely long‐lived and potentially toxic. A successive selective and controllable C( sp 3 )−F functionalization of polyfluoroalkylated ketones with S ‐ and O ‐nucleophiles to enable efficient synthesis of pharmaceutically important fluorine‐ and sulfur‐containing polycyclic furan and chromene derivatives under transition metal‐free conditions is demonstrated here. The combination of C−S/C−O coupling, aromatization, and cyclization cascade contribute to the accurate four/five C( sp 3 )−F bond cleavage at two different sites of perfluoroalkyl chain. The formation of reactive quinoid intermediates and the necessity of using TBAB (tetrabutylammonium bromide) as additive and Cs 2 CO 3 as base were identified by detailed mechanistic studies. magnified image" @default.
• W3080737942 created "2020-09-01" @default.
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• W3080737942 date "2020-09-17" @default.
• W3080737942 modified "2023-10-12" @default.
• W3080737942 title "Synthesis of Polycyclic Furan and Chromene Derivatives <i>via</i> Cascade Reactions Enabled by Cleavage of Multiple C( <i>sp</i> ³ )−F Bonds" @default.
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• W3080737942 doi "https://doi.org/10.1002/adsc.202000660" @default.
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