Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 46, Pages 15153-15156Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809679
Keywords
C-H functionalization; heterocycles; oximes; paired electrolysis; radicals
Categories
Funding
- MOST [2016YFA0204100]
- NSFC [21672178]
- Fundamental Research Funds for the Central Universities
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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.
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