4.6 Article

9-Borabicyclo[3.3.l]nonane-induced Friedel-Crafts benzylation of arenes with benzyl fluorides

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 21, Pages 5258-5261

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob00912d

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Funding

  1. NSERC of Canada
  2. Canada Research Chair
  3. Visiting Einstein Fellowship at TU Berlin
  4. NSERC CGS-D scholarship

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Friedel-Crafts benzylation of arenes with benzyl fluorides using 9-borabicyclo[3.3.l]nonane (9-BBN) as a mediator has been developed. This provides a simple and cheap route to the activation of C-F bonds to synthesize 1,1-diarylmethanes in good to excellent yields (up to 98%) under mild conditions. Functional group tolerance and the mechanism are considered.

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