Cathode Material Determines Product Selectivity for Electrochemical C−H Functionalization of Biaryl Ketoximes

The synthesis of polycyclic N‐heteroaromatic compounds and their corresponding N‐oxides has been developed through electrochemical C−H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wid...

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Bibliographic Details
Published in:Angewandte Chemie 2018-11, Vol.130 (46), p.15373-15376
Main Authors: Zhao, Huai‐Bo, Xu, Pin, Song, Jinshuai, Xu, Hai‐Chao
Format: Article
Language:English
Subjects:
C-H-Funktionalisierung
Cathodes
Chemistry
Dehydrogenation
Deoxygenation
Electrochemistry
Electrode materials
Gekoppelte Elektrolyse
Heterocyclen
Heterocyclic compounds
Oxides
Oxime
Radikale
Selectivity
Substrates
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Summary:The synthesis of polycyclic N‐heteroaromatic compounds and their corresponding N‐oxides has been developed through electrochemical C−H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wide range of N‐heteroaromatic N‐oxides. The products of the electrosynthesis are switched to the deoxygenated N‐heteroaromatics by employing a Pb cathode through sequential anode‐promoted dehydrogenative cyclization and cathodic cleavage of the N−O bond in the initially formed N‐oxide. Gespaltene Persönlichkeit: Eine divergente Synthese von polycyclischen N‐Heteroarenen und den entsprechenden N‐Oxiden durch elektrochemische C‐H‐Funktionalisierung von Biarylketoximen wurde entwickelt. Die Wahl des Kathodenmaterials steuert die Produktselektivität.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201809679