Organophotochemical S N Ar Reactions of Mildly Electron‐Poor Fluoroarenes

C–F functionalization of arenes with a range of alcohol and pyrazole nucleophiles has been achieved without the need for metal catalysts or highly electron‐poor substrates. Treatment of fluoroarenes with alcohols or pyrazoles and DDQ under irradiation by blue LED light provides the corresponding sub...

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Published inEuropean journal of organic chemistry Vol. 2020; no. 18; pp. 2766 - 2770
Main Authors Sheridan, Thomas, Yayla, Hatice G., Lian, Yajing, Genovino, Julien, Monck, Nat, Burton, Jonathan W.
Format Journal Article
LanguageEnglish
Published 14.05.2020
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Summary:C–F functionalization of arenes with a range of alcohol and pyrazole nucleophiles has been achieved without the need for metal catalysts or highly electron‐poor substrates. Treatment of fluoroarenes with alcohols or pyrazoles and DDQ under irradiation by blue LED light provides the corresponding substituted products. The procedure is complementary to classical S N Ar chemistry which generally requires basic reaction conditions and high temperatures, and provides products under non‐basic conditions at ≈ 40 °C.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000337