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Visible-Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C,N-Diacyliminium Ions |
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| Authors: | Mario Frahm Thorsten von Drathen Lisa Marie Gronbach Alice Voss Felix Lorenz Jonas Bresien Alexander Villinger Frank Hoffmann Prof?Dr Malte Brasholz |
| Institution: | 1. Institute of Chemistry, University of Rostock, Albert-Einstein-Str. 3A, 18059 Rostock, Germany;2. Department of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
These authors contributed equally to this work.;3. Institute of Chemistry, University of Rostock, Albert-Einstein-Str. 3A, 18059 Rostock, Germany These authors contributed equally to this work.;4. Department of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany |
| Abstract: | Tetrahydrocarbazoles and perhydrocycloheptab]indoles undergo a catalytic cascade singlet oxygenation in alkaline medium, which leads to chiral tricyclic perhydropyrido- and perhydroazepino1,2-a]indoles in a single operation. These photooxygenation products are new synthetic equivalents of uncommon C,N-diacyliminium ions and can be functionalized with the aid of phosphoric acid organocatalysis. |
| Keywords: | cascade reactions indoles N-acyliminium ions photooxidation singlet oxygen |