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Decarboxylative/Oxidative Amidation of Aryl α‑Ketocarboxylic Acids with Nitroarenes and Nitroso Compounds in Aqueous Medium

The decarboxylative/oxidative amidation of aryl α-ketocarboxylic acids with 5-aryl-3-nitroisoxazole-4-carboxylates and substituted dinitrobenzenes under oxidative aqueous conditions to afford N-aryl amides is described. The reaction is suggested to proceed via a radical pathway in which a benzoyl ni...

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Bibliographic Details
Published in:Organic letters 2020-12, Vol.22 (23), p.9381-9385
Main Authors: Barak, Dinesh S, Dahatonde, Dipak J, Dighe, Shashikant U, Kant, Ruchir, Batra, Sanjay
Format: Article
Language:English
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Summary:The decarboxylative/oxidative amidation of aryl α-ketocarboxylic acids with 5-aryl-3-nitroisoxazole-4-carboxylates and substituted dinitrobenzenes under oxidative aqueous conditions to afford N-aryl amides is described. The reaction is suggested to proceed via a radical pathway in which a benzoyl nitroxyl radical, the key intermediate formed from reaction between nitroarene and benzoyl radical from glyoxalic acid, couples with hydroxyl radical from water to produce amide. Mechanistic insight allowed the scope of the strategy to be expanded to the synthesis of amides via reaction between aryl α-ketocarboxylic acids and nitroso compounds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03666