Department of Chemistry and Biochemistry, University of Arizona, Tucson, Arizona 85721, United States.
J Am Chem Soc. 2020 Jul 15;142(28):12056-12061. doi: 10.1021/jacs.0c05507. Epub 2020 Jul 5.
Red light has the advantages of low energy, less health risks, and high penetration depth through various media. Herein, a helical carbenium ion (-di--propyl-1,13-dimethoxyquinacridinium (Pr-DMQA) tetrafluoroborate) has been used as an organic photoredox catalyst for photoreductions and photooxidations in the presence of red light (λ = 640 nm). It has catalyzed red-light-mediated dual transition-metal/photo-redox-catalyzed C-H arylation and intermolecular atom-transfer radical addition through oxidative quenching. Moreover, its potential in photooxidation catalysis has also been demonstrated by successful applications in red-light-induced aerobic oxidative hydroxylation of arylboronic acids and benzylic C(sp)-H oxygenation through reductive quenching. Thus, a versatile organic photoredox catalyst (helical carbenium ion) for red-light-mediated photoredox reactions has been developed.
红光具有能量低、健康风险小、能穿透各种介质等优点。在此，我们使用一种螺旋碳鎓离子（-二丙基-1,13-二甲氧基喹吖啶鎓（Pr-DMQA）四氟硼酸盐）作为有机光氧化还原催化剂，在红光（λ = 640nm）存在下进行光还原和光氧化反应。它通过氧化猝灭催化了红光介导的双过渡金属/光氧化还原催化的 C-H 芳基化和分子间原子转移自由基加成反应。此外，通过还原猝灭成功地将其应用于红光诱导的芳基硼酸的有氧氧化羟基化和苄位 C(sp)-H 的氧化，证明了其在光氧化催化中的潜在应用。因此，开发了一种用于红光介导的光氧化还原反应的多功能有机光氧化还原催化剂（螺旋碳鎓离子）。
