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Direct Electrochemical Synthesis of 2,3‐Disubstituted Quinoline N‐ oxides by Cathodic Reduction of Nitro Arenes

Winter, Johannes; Prenzel, Tobias; Wirtanen, Tom; Schollmeyer, Dieter; Waldvogel, Siegfried R.

Abstract:

The use of electric current in synthetic organic chemistry offers a sustainable tool for the selective reductive synthesis of quinoline N-oxides starting from easily accessible nitro compounds. The reported method employs mild and reagent-free conditions, a simple undivided cell, and constant current electrolysis set-up which provides conversion with a high atom economy. The synthesis of 30 differently substituted quinoline N-oxides was successfully performed in up to 90 % yield. Using CV studies, the mechanism of the selective formation of the quinoline N-oxides was elucidated. The technical relevance of the described reaction could be shown in a 50-fold scale-up reaction.


Verlagsausgabe §
DOI: 10.5445/IR/1000168473
Veröffentlicht am 15.02.2024
Originalveröffentlichung
DOI: 10.1002/chem.202203319
Scopus
Zitationen: 7
Web of Science
Zitationen: 7
Dimensions
Zitationen: 10
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 24.02.2023
Sprache Englisch
Identifikator ISSN: 0947-6539, 1521-3765
KITopen-ID: 1000168473
HGF-Programm 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in Chemistry – A European Journal
Verlag John Wiley and Sons
Band 29
Heft 12
Seiten e202203319
Vorab online veröffentlicht am 16.01.2023
Nachgewiesen in Web of Science
Scopus
Dimensions
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