Triangulenium Ions: Versatile Organic Photoredox Catalysts for Green-Light-Mediated Reactions
Triangulenium Ions: Versatile Organic Photoredox Catalysts for Green-Light-Mediated Reactions
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DOI：
10.1055/a-2117-8928
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发表时间：
2023-09-18
期刊：
影响因子：
2
通讯作者：
Gianetti，Thomas L.
中科院分区：
文献类型：
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作者：
Nowack，Marko H.;Moutet，Jules;Gianetti，Thomas L.
可调有机光氧化还原催化剂的开发是光氧化还原催化领域的一个重要研究方向。高度模块化和可调的triangulenium家族（azadioxatriangulenium、diazaoxatriangulenium和triazatriangulenium）和相关的[4]螺烯喹吖啶鎓（helicene quinacridinium）已被用作有机光氧化还原催化剂，用于在可见光照射（λ = 518-640 nm）下的光还原和光氧化。光氧化还原催化剂家族的一个亮点是其易于调节的氧化还原性质，从而导致不同的反应性。报道了它们作为光催化剂用于芳基硼酸的有氧氧化羟基化反应和N-苯基-1，2，3，5-四氢异喹啉与硝基甲烷的有氧交叉偶联反应。此外，它们作为光还原催化剂的潜力已被证明通过氧化猝灭的分子间原子转移自由基加成的催化。这些转换作为基准，以突出容易合成的trianguleniums，同系物的吖啶，是通用的有机光氧化还原催化剂与应用在光氧化和光还原。
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 (λ = 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 ofN-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.