Triangulenium Ions: Versatile Organic Photoredox Catalysts for Green-Light-Mediated Reactions
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Triangulenium Ions : Versatile Organic Photoredox Catalysts for Green-Light-Mediated Reactions. / Nowack, Marko Heine; Moutet, Jules; Laursen, Bo W.; Gianetti, Thomas L.
I: Synlett, Bind 35, Nr. 03, 2024, s. 307-312.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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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 -
ID: 371552209