TY - JOUR

T1 - Triangulenium Ions

T2 - Versatile Organic Photoredox Catalysts for Green-Light-Mediated Reactions

AU - Nowack, Marko Heine

AU - Moutet, Jules

AU - Laursen, Bo W.

AU - Gianetti, Thomas L.

N1 - Publisher Copyright: © 2023 Georg Thieme Verlag. All rights reserved.

PY - 2024

Y1 - 2024

N2 - The development of tunable organic photoredox catalysts remains important in the field of photoredox catalysis. Herein, the highly modu-lar and tunable family of trianguleniums (azadioxa triangulenium, diazaoxa triangulenium, and triaza triangulenium), and the related [4]helicene quinacridinium have been used as organic photoredox catalysts for photoreductions and photooxidations under visible light (518-640 nm). This family of photoredox catalysts is highlighted by the readily tunable redox properties leading to different reactivies. We report their use as photocatalysts for the aerobic oxidative hydroxyla-tion of arylboronic acids and the aerobic cross-dehydrogenative cou-pling reaction of N-phenyltetrahydroisoquinoline with nitromethane through reductive quenching. Furthermore, their potential as photore-duction catalysts has been show through the catalysis of intermolecular atom-transfer radical addition via oxidative quenching. These transfor-mations serve as a benchmark to highlight that the easily synthesized trianguleniums, congeners to the acridiniums, are versatile organic photoredox catalysts with applications in both photooxidations and photoreductions.

AB - The development of tunable organic photoredox catalysts remains important in the field of photoredox catalysis. Herein, the highly modu-lar and tunable family of trianguleniums (azadioxa triangulenium, diazaoxa triangulenium, and triaza triangulenium), and the related [4]helicene quinacridinium have been used as organic photoredox catalysts for photoreductions and photooxidations under visible light (518-640 nm). This family of photoredox catalysts is highlighted by the readily tunable redox properties leading to different reactivies. We report their use as photocatalysts for the aerobic oxidative hydroxyla-tion of arylboronic acids and the aerobic cross-dehydrogenative cou-pling reaction of N-phenyltetrahydroisoquinoline with nitromethane through reductive quenching. Furthermore, their potential as photore-duction catalysts has been show through the catalysis of intermolecular atom-transfer radical addition via oxidative quenching. These transfor-mations serve as a benchmark to highlight that the easily synthesized trianguleniums, congeners to the acridiniums, are versatile organic photoredox catalysts with applications in both photooxidations and photoreductions.

KW - Heterocyclic Fused Cationic Compounds

KW - Organic Photoredox Catalysis

KW - Photooxidation

KW - Photoreduction

KW - Trianguleniums

KW - Versatile Redox Properties

U2 - 10.1055/a-2117-8928

DO - 10.1055/a-2117-8928

M3 - Journal article

AN - SCOPUS:85164980185

VL - 35

SP - 307

EP - 312

JO - SYNLETT: Accounts and Rapid Communications in Chemical Synthesis

JF - SYNLETT: Accounts and Rapid Communications in Chemical Synthesis

SN - 0936-5214

IS - 03

ER -