Visible Light Photoredox Catalysis: Generation and Addition of N-Aryltetrahydroisoquinoline-Derived alpha-Amino Radicals to Michael Acceptors

Kohls, Paul and Jadhav, Deepak and Pandey, Ganesh and Reiser, Oliver (2012) Visible Light Photoredox Catalysis: Generation and Addition of N-Aryltetrahydroisoquinoline-Derived alpha-Amino Radicals to Michael Acceptors. ORGANIC LETTERS, 14 (3). pp. 672-675. ISSN 1523-7060, 1523-7052

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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)]PF6 in combination with irradiation at 455 nm generated by a blue LED, demonstrating the trapping of visible light generated alpha-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.

Item Type: Article
Uncontrolled Keywords: PHOTOINDUCED REDOX REACTIONS; ELECTRON-DEFICIENT ALKENES; TERTIARY-AMINES; PHOTOCHEMICAL ADDITION; ORGANIC-SYNTHESIS; HIGHLY EFFICIENT; BOND FORMATION; TRANSFER PET; C-C; PHOTOCATALYSIS;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 19 May 2020 09:01
Last Modified: 19 May 2020 09:01
URI: https://pred.uni-regensburg.de/id/eprint/19242

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