Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C, N‐Diacyliminium Ions. Issue 30 (23rd June 2020)

• Record Type: Journal Article
• Authors: Frahm, Mario; von Drathen, Thorsten; Gronbach, Lisa Marie; Voss, Alice; Lorenz, Felix; Bresien, Jonas; Villinger, Alexander; Hoffmann, Frank; Brasholz, Malte
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 30(2020)
• Page Start: 12450
• Page End: 12454
• Publication Date: 2020-06-23
• Subjects: cascade reactions -- indoles -- N-acyliminium ions -- photooxidation -- singlet oxygen; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202007549
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Tetrahydrocarbazoles and perhydrocyclohepta[b]indoles undergo a catalytic cascade singlet oxygenation in alkaline medium, which leads to chiral tricyclic perhydropyrido‐ and perhydroazepino[1, 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. Abstract : Splashing down the ponds : The cascade photooxygenation of tetrahydrocarbazoles and cyclohepta[ b ]indoles leads to chiral tricyclic perhydropyrido‐ and perhydroazepino[1, 2‐ a ]indoles, which are precursors to uncommon C, N ‐diacyliminium ions.