Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2019

Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

Résumé

We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)–H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)–H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.

Domaines

Chimie
Fichier principal
Vignette du fichier
Yuan et al_2019_Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides.pdf (1.29 Mo) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)
Loading...

Dates et versions

hal-02020140 , version 1 (16-05-2019)

Identifiants

Citer

Yu-Chao Yuan, Christian Bruneau, Vincent Dorcet, Thierry Roisnel, Rafael Gramage-Doria. Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides. Journal of Organic Chemistry, 2019, 84 (4), pp.1898-1907. ⟨10.1021/acs.joc.8b02899⟩. ⟨hal-02020140⟩
81 Consultations
352 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More