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

Jian Luo, Jian Zhang

Research output: Contribution to journalArticle

223 Scopus citations

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 languageEnglish (US)
Pages (from-to)873-877
Number of pages5
JournalACS Catalysis
Volume6
Issue number2
DOIs
StatePublished - Feb 5 2016

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Keywords

  • cross-coupling
  • donor-acceptor fluorophores
  • nickel catalysis
  • photoredox catalysis
  • visible light

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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