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

Chemistry : a European Journal
Karlee L BamfordDouglas W Stephan

Abstract

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.

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Citations

Dec 25, 2019·Chemical Communications : Chem Comm·Evan A Patrick, Warren E Piers
May 21, 2019·Organic & Biomolecular Chemistry·Jing GuoDouglas W Stephan
Mar 7, 2020·Organic Letters·Liyan FuYasushi Nishihara
Jul 1, 2020·Chemical Reviews·Minyan Wang, Zhuangzhi Shi

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