American Chemical Society
cs6b00866_si_001.pdf (8.86 MB)

Autocatalytic Friedel–Crafts Reactions of Tertiary Aliphatic Fluorides Initiated by B(C6F5)3·H2O

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journal contribution
posted on 2016-05-04, 00:00 authored by Marian Dryzhakov, Joseph Moran
The C–F bond is the strongest single bond to carbon, constituting an intrinsic challenge for selective catalytic activation in the presence of other functional groups. Existing methods for the activation of tertiary aliphatic fluorides involve stoichiometric abstraction with fluorophilic Lewis acids or by Lewis-acid-catalyzed trapping with Si reagents. Herein, we describe a B­(C6F5)3·H2O-catalyzed Friedel–Crafts reaction of tertiary alkyl fluorides that proceeds rapidly at room temperature without trapping reagents. The method is completely selective for F over traditionally better leaving groups and displays an autocatalytic kinetic profile.