Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 60, Pages 16014-16018Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201804705
Keywords
Alkyl-fluorides; borylation; C-F reduction; Friedel-Crafts; hydridoboranes
Categories
Funding
- NSERC of Canada
- Canada Research Chair
- NSERC CGS-D scholarship
- Deutsche Forschungsgemeinschaft
- TU Berlin
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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(C6F5)(2)) are described. While HBcat, 9-BBN and HB(C6F5)(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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