Triangulenium Ions: Versatile Organic Photoredox Catalysts for Green-Light-Mediated Reactions

Marko H. Nowack, Jules Moutet, Bo W. Laursen, Thomas L. Gianetti

Research output: Contribution to journalArticlepeer-review

Abstract

The development of tunable organic photoredox catalysts remains important in the field of photoredox catalysis. A highly modular and tunable family of trianguleniums (azadioxatriangulenium, diazaoxatriangulenium, and triazatriangulenium), and the related [4]helicene quinacridinium have been used as organic photoredox catalysts for photoreductions and photooxidations under visible light irradiation (O = 518.640 nm). A highlight of this family of photoredox catalysts is their readily tunable redox properties, leading to different reactivities. We report their use as photocatalysts for the aerobic oxidative hydroxylation of arylboronic acids and the aerobic cross-dehydrogenative coupling reaction of N-phenyl-1,2,3,5-tetrahydroisoquinoline with nitromethane through reductive quenching. Furthermore, their potential as photoreduction catalysts has been demonstrated through the catalysis of an intermolecular atom-transfer radical addition via oxidative quenching. These transformations serve as benchmarks to highlight that the easily synthesized trianguleniums, congeners of the acridiniums, are versatile organic photoredox catalysts with applications in both photooxidations and photoreductions.

Original languageEnglish (US)
Pages (from-to)307-312
Number of pages6
JournalSynlett
Volume35
Issue number3
DOIs
StatePublished - Jun 2 2023

Keywords

  • heterocyclic fused cationic compounds
  • photooxidation
  • photoredox organocatalysis
  • photoreduction
  • trianguleniums

ASJC Scopus subject areas

  • Organic Chemistry

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