Chlorophyll-Catalyzed Visible-Light-Mediated Synthesis of Tetrahydroquinolines from N,N‑Dimethylanilines and Maleimides

Natural pigment chlorophyll was used as a green photosensitizer for the first time in a visible-light photoredox catalysis for the efficient synthesis of tetrahydroquinolines from N,N-dimethylanilines and maleimides in an air atmosphere. The reaction involves direct cyclization via an sp3 C–H bond f...

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Veröffentlicht in:Journal of organic chemistry 2017-02, Vol.82 (4), p.1888-1894
Hauptverfasser: Guo, Jun-Tao, Yang, Da-Cheng, Guan, Zhi, He, Yan-Hong
Format: Artikel
Sprache:eng
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Zusammenfassung:Natural pigment chlorophyll was used as a green photosensitizer for the first time in a visible-light photoredox catalysis for the efficient synthesis of tetrahydroquinolines from N,N-dimethylanilines and maleimides in an air atmosphere. The reaction involves direct cyclization via an sp3 C–H bond functionalization process to afford products in moderate to high yields (61–98%) from a wide range of substrates with a low loading of chlorophyll under mild conditions. This work demonstrates the potential benefits of chlorophyll as photosensitizer in visible light catalysis.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b03034