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Rongalite/iodine-mediated C(sp 3 )-H bond oximation and thiomethylation reaction of methyl ketones using copper nitrate as the [NO] reagent: synthesis of thiohydroximic acids.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2024 Sep 02. Date of Electronic Publication: 2024 Sep 02. - Publication Year :
- 2024
- Publisher :
- Ahead of Print
-
Abstract
- 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 <subscript>2</subscript> radical or the NO <subscript>2</subscript> radical dimeric forms as an ion-pair equivalent to participate in the transformation.
Details
- Language :
- English
- ISSN :
- 1477-0539
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 39222034
- Full Text :
- https://doi.org/10.1039/d4ob01217h