Visible- and UV-Light-Induced Decarboxylative Radical Reactions of Benzoic Acids Using Organic Photoredox Catalysts

Photoinduced decarboxylative radical reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions and mild heating afforded adducts, arylboronate esters, and the reduction product, respectively. The reaction is thought to involv...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-04, Vol.85 (8), p.5362-5369
Main Authors: Kubosaki, Suzuka, Takeuchi, Haruka, Iwata, Yutaka, Tanaka, Yosuke, Osaka, Kazuyuki, Yamawaki, Mugen, Morita, Toshio, Yoshimi, Yasuharu
Format: Article
Language:English
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Summary:Photoinduced decarboxylative radical reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions and mild heating afforded adducts, arylboronate esters, and the reduction product, respectively. The reaction is thought to involve single-electron transfer promoted the generation of aryl radicals via decarboxylation. A diverse range of benzoic acids were found to be suitable substrates for this photoreaction. Only our two-molecule organic photoredox system can work well for the direct photoinduced decarboxylation of benzoic acids.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00055