Interactions of C-F Bonds with Hydridoboranes: Reduction, Borylation and Friedel-Crafts Alkylation.

The stoichiometric reactions of the alkylfluorides 1-fluoroadamantane (Ad-F), fluorocyclohexane (Cy-F), 1-fluoropentane (Pent-F) and benzyl fluorides with secondary boranes pinacolborane (HBpin), catecholborane (HBcat), 9-borabicyclo(3.3.1)nonane (9-BBN) and Piers' borane (HB(C6 F5 )2 ) are described. While HBcat, 9-BBN and HB(C6 F5 )2 reduce Ad-F to Ad-H, the latter borane was shown to react with secondary and primary fluoroalkanes, affording C-F borylation, while benzyl fluorides undergo Friedel-Crafts chemistry.