Visible Light Photoredox Catalysis: Generation and Addition of N-Aryltetrahydroisoquinoline-Derived α-Amino Radicals to Michael Acceptors
Organic Letters2012Vol. 14(3), pp. 672–675
Citations Over TimeTop 1% of 2012 papers
Abstract
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.
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