Donor–Acceptor Fluorophores for Visible-Light-Promoted Organic Synthesis: Photoredox/Ni Dual Catalytic C(sp3)–C(sp2) Cross-Coupling

We describe carbazolyl dicyanobenzene (CDCB)-based donor–acceptor (D–A) fluorophores as a class of cheap, easily accessible, and efficient metal-free photoredox catalysts for organic synthesis. By changing the number and position of carbazolyl and cyano groups on the center benzene ring, CDCBs with...

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Bibliographic Details
Published inACS catalysis Vol. 6; no. 2; pp. 873 - 877
Main Authors Luo, Jian, Zhang, Jian
Format Journal Article
LanguageEnglish
Published American Chemical Society 05.02.2016
Subjects
cross-coupling
donor−acceptor fluorophores
photoredox catalysis
visible light
nickel catalysis
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Summary:We describe carbazolyl dicyanobenzene (CDCB)-based donor–acceptor (D–A) fluorophores as a class of cheap, easily accessible, and efficient metal-free photoredox catalysts for organic synthesis. By changing the number and position of carbazolyl and cyano groups on the center benzene ring, CDCBs with a wide range of photoredox potentials are obtained to effectively drive the energetically demanding C­(sp3)–C­(sp2) cross-coupling of carboxylic acids and alkyltrifluoroborates with aryl halides via a photoredox/Ni dual catalysis mechanism. This work validates the utility of D–A fluorophores in guiding the rational design of metal-free photoredox catalysts for visible-light-promoted organic synthesis.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.5b02204