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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| Published in | ACS catalysis Vol. 6; no. 2; pp. 873 - 877 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
American Chemical Society
05.02.2016
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| Subjects | |
| Online Access | Get full text |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Zhang, Jian Luo, Jian |
| AuthorAffiliation | Department of Chemistry University of Nebraska−Lincoln |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: University of Nebraska−Lincoln |
| Author_xml | – sequence: 1 givenname: Jian surname: Luo fullname: Luo, Jian – sequence: 2 givenname: Jian surname: Zhang fullname: Zhang, Jian email: jzhang3@unl.edu |
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| Keywords | cross-coupling donor−acceptor fluorophores photoredox catalysis visible light nickel catalysis |
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| Snippet | We describe carbazolyl dicyanobenzene (CDCB)-based donor–acceptor (D–A) fluorophores as a class of cheap, easily accessible, and efficient metal-free... |
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| StartPage | 873 |
| Title | Donor–Acceptor Fluorophores for Visible-Light-Promoted Organic Synthesis: Photoredox/Ni Dual Catalytic C(sp3)–C(sp2) Cross-Coupling |
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