Rongalite/iodine-mediated C(sp)-H bond oximation and thiomethylation reaction of methyl ketones using copper nitrate as the [NO] reagent: synthesis of thiohydroximic acids

In this work, a highly efficient rongalite/iodine-mediated oxime formation reaction for the preparation of thiohydroximic acids from methyl ketones by employing copper nitrate as the [NO] reagent has been developed. Notably, copper nitrate participated as both a catalyst and the mild oximation reage...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-09, Vol.22 (37), p.7623-7627
Main Authors: Wang, Miao, Ren, Hui-Ying, Pu, Xiao-Yu, Zhang, Xiao-Lu, Zhu, He-Ying, Wu, An-Xin, Zhao, Bang-Tun
Format: Article
Language:English
Subjects:
Catalysts
Chemical synthesis
Copper
Copper converters
Hydrogen bonds
Iodine
Ion pairs
Ketones
Natural products
Nitrates
Nitrogen dioxide
Reagents
Substrates
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Summary:In this work, a highly efficient rongalite/iodine-mediated oxime formation reaction for the preparation of thiohydroximic acids from methyl ketones by employing copper nitrate as the [NO] reagent has been developed. Notably, copper nitrate participated as both a catalyst and the mild oximation reagent in the transformation. This reaction is highly efficient and facile, with a broad substrate scope, especially for fused ring skeleton substrates, heterocyclic skeleton substrates, and acetyl-substituted natural products. Mechanistic studies revealed that copper nitrate might be converted into a NO 2 radical or the NO 2 radical dimeric forms as an ion-pair equivalent to participate in the transformation. Rongalite/iodine-mediated oxime formation reaction for the synthesis of thiohydroximic acids from methyl ketones by employing copper nitrate as the [NO] reagent was developed.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob01217h