Synthesis of N-heterocyclic amides from imidazoheterocycles through convergent paired electrolysis

An efficient ring opening of imidazoheterocycles induced by a direct C-H azidation resulting in an unusual formation of N-heterocyclic amides has been successfully developed through convergent paired electrolysis. A broad scope of pyridylbenzamides could be obtained in moderate to excellent yields u...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-11, Vol.22 (44), p.873-8736
Main Authors: Leclercq, Elise, Chevet, Laura, David, Nicolas, Durandetti, Muriel, Chausset-Boissarie, Laëtitia
Format: Article
Language:English
Subjects:
Amides
Chemical Sciences
Continuous flow
Electrochemistry
Electrolysis
Organic chemistry
Other
Oxidants
Oxidizing agents
Ring opening
Citations: Items that this one cites
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Summary:An efficient ring opening of imidazoheterocycles induced by a direct C-H azidation resulting in an unusual formation of N-heterocyclic amides has been successfully developed through convergent paired electrolysis. A broad scope of pyridylbenzamides could be obtained in moderate to excellent yields under exogenous-oxidant, electrolyte- and metal-free electrochemical conditions. The methodology was transferred to continuous flow conditions resulting in notable improvements particularly in terms of cost-efficiency over traditional batch versions. Herein, we present a novel electrochemical approach for the synthesis of N-heterocyclic amides with moderate to excellent yields in batch and flow.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d4ob01115e