Journal
ACS CATALYSIS
Volume 6, Issue 2, Pages 873-877Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b02204
Keywords
donor-acceptor fluorophores; photoredox catalysis; nickel catalysis; visible light; cross-coupling
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Funding
- University of Nebraska-Lincoln
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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(sp(3))-C(sp(2)) 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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