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- W4226268424 abstract "We present here a copper-catalyzed electrophilic ortho C-H amination of protected naphthylamines with N-(benzoyloxy)amines, cyclization with the pendant amide, and carbon to nitrogen 1,2-directing group migration cascade to access N,N-disubstituted 2-benzimidazolinones. Remarkably, this highly atom-economic tandem reaction proceeds through a C-H and C-C bond cleavage and three new C-N bond formations in a single operation. Intriguingly, the reaction cascade was altered by the subtle tuning of the directing group from picolinamide to thiopicolinamide furnishing 2-heteroaryl-imidazoles via the extrusion of hydrogen sulfide. This strategy provided a series of benzimidazolones and benzimidazoles in moderate to high yields with low catalyst loading (66 substrates with yields up to 99%). From the control experiments, it was observed that after the C-H amination an incipient tetrahedral oxyanion or thiolate intermediate is formed via an intramolecular attack of the primary amine to the amide/thioamide carbonyl. It undergoes either a 1,2-pyridyl shift with the retention of the carbonyl moiety or H2S elimination for scaffold diversification. Remarkably, inspite of a positive influence of copper in the reaction outcome, from our preliminary investigations, the benzimidazolone product was obtained in good to moderate yields in two steps under metal-free conditions. The N-pyridyl moiety of the benzimidazolone was removed for further manipulation of the free NH group." @default.
- W4226268424 created "2022-05-05" @default.
- W4226268424 creator A5019706746 @default.
- W4226268424 creator A5023300512 @default.
- W4226268424 creator A5080912808 @default.
- W4226268424 date "2022-01-01" @default.
- W4226268424 modified "2023-10-01" @default.
- W4226268424 title "A directing group switch in copper-catalyzed electrophilic C–H amination/migratory annulation cascade: divergent access to benzimidazolone/benzimidazole" @default.
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- W4226268424 doi "https://doi.org/10.1039/d2sc01420c" @default.
- W4226268424 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/35694354" @default.
- W4226268424 hasPublicationYear "2022" @default.
- W4226268424 type Work @default.