Visible‐Light‐Mediated α‐Oxygenation of 3‐(N,N‐Dimethylaminomethyl)‐Indoles to Aldehydes

The visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents afforded a series of 3‐carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)‐vi...

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Veröffentlicht in:European journal of organic chemistry 2018-12, Vol.2018 (47), p.6624-6628
Hauptverfasser: Stanek, Filip, Pawłowski, Robert, Mlynarski, Jacek, Stodulski, Maciej
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Sprache:eng
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Zusammenfassung:The visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents afforded a series of 3‐carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)‐vincorine is described as well. 3‐Carbaindole derivatives can be accessed through a visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents. A plausible mechanism and practical application of this transformation in formal synthesis of (–)‐Vincorine is also described.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201801335