4.7 Article

A Continuous-Flow Protocol for Light-Induced Benzylic Fluorinations

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 17, Pages 8486-8490

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo5016757

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Funding

  1. Eli Lilly and Company through the Lilly Research Award Program (LRAP)
  2. NAWI Graz

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A continuous-flow protocol for the light-induced fluorination of benzylic compounds is presented. The procedure uses Selectfluor as the fluorine source and xanthone as an inexpensive and commercially available photoorganocatalyst. The flow photoreactor is based on transparent fluorinated ethylene propylene tubing and a household compact fluorescent lamp. The combination of xanthone with black-light irradiation results in very efficient fluorination. Good to excellent isolated yields were obtained for a variety of substrates bearing different functional groups applying residence times below 30 mm.

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