Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[ b ]indoles: Access to  C , N ‐Diacyliminium Ions | Zendy

Frahm Mario | Zendy; Drathen Thorsten | Zendy; Gronbach Lisa Marie | Zendy; Voss Alice | Zendy; Lorenz Felix | Zendy; Bresien Jonas | Zendy; Villinger Alexander | Zendy; Hoffmann Frank | Zendy; Brasholz Malte | Zendy

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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

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.

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