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Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[ b ]indoles: Access to C , N ‐Diacyliminium Ions
Author(s) -
Frahm Mario,
Drathen Thorsten,
Gronbach Lisa Marie,
Voss Alice,
Lorenz Felix,
Bresien Jonas,
Villinger Alexander,
Hoffmann Frank,
Brasholz Malte
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007549
Subject(s) - photooxygenation , chemistry , phosphoric acid , organocatalysis , cascade , ion , catalysis , singlet state , photochemistry , singlet oxygen , combinatorial chemistry , organic chemistry , enantioselective synthesis , physics , oxygen , chromatography , nuclear physics , excited state
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.