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.
Original language | English (US) |
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Pages (from-to) | 873-877 |
Number of pages | 5 |
Journal | ACS Catalysis |
Volume | 6 |
Issue number | 2 |
DOIs | |
State | Published - Feb 5 2016 |
Keywords
- cross-coupling
- donor-acceptor fluorophores
- nickel catalysis
- photoredox catalysis
- visible light
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)