Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053 Regensburg, Germany.
Org Lett. 2012 Feb 3;14(3):672-5. doi: 10.1021/ol202857t. Epub 2012 Jan 19.
The photoredox-catalyzed coupling of N-aryltetrahydroisoquinoline and Michael acceptors was achieved using Ru(bpy)(3)Cl(2) or [Ir(ppy)(2)(dtb-bpy)]PF(6) in combination with irradiation at 455 nm generated by a blue LED, demonstrating the trapping of visible light generated α-amino radicals. While intermolecular reactions lead to products formed by a conjugate addition, in intramolecular variants further dehydrogenation occurs, leading directly to 5,6-dihydroindolo[2,1-a]tetrahydroisoquinolines, which are relevant as potential immunosuppressive agents.
通过使用 Ru(bpy)(3)Cl(2) 或 [Ir(ppy)(2)(dtb-bpy)]PF(6) 与在 455nm 下由蓝色 LED 产生的光辐照相结合，实现了 N-芳基四氢异喹啉和迈克尔受体的光氧化还原催化偶联，证明了可见光生成的α-氨基自由基的捕获。虽然分子间反应导致通过共轭加成形成产物，但在分子内变体中进一步发生脱氢反应，直接生成 5,6-二氢吲哚[2,1-a]四氢异喹啉，它们作为潜在的免疫抑制剂具有相关性。
