A Continuous-Flow Protocol for Light-Induced Benzylic Fluorinations

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 pr...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 79; no. 17; pp. 8486 - 8490
Main Authors Cantillo, David, de Frutos, Oscar, Rincón, Juan A, Mateos, Carlos, Kappe, C. Oliver
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.09.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
C-H FLUORINATION
PHOTOREDOX CATALYSIS
TRIFLUOROMETHYLATION
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Summary: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 min.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5016757