RESUMEN
A general copper/air catalytic system for selectively oxidative C-C bond cleavage of 1,2-diarylethan-1-one has been developed, giving aromatic aldehydes and N-benzoylation products of various amines in moderate to excellent yields. This research provides an alternative approach for the N-benzoylation of amine in mild and neutral conditions.
RESUMEN
A rhodium(III)-catalyzed strategy for the one-step synthesis of polysubstituted cis-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-1-ones from simple 2'-hydroxychalcones and alkynes is developed. This novel transformation involves a sequential C-C bond cleavage and dehydrogenative annulation, leading to the product bearing a quaternary and a tertiary carbon center. 13C labeling experiments revealed that C-C bond cleavage takes place not only at the C-C(CâO) bond but also at the C≡C bond. This study provides an alternative strategy using C-C bond cleavage thus demonstrating the power of this strategy combined with C-H bond functionalization for assembling complex structures from simple starting materials.
RESUMEN
A unique copper-catalyzed aerobic oxidative C-C bond cleavage of simple unstrained ketones with air and amines has been developed. In this chemistry, amides and oxo amides are easily synthesized through the selective C-C bond cleavage of simple ketones or unstrained cycloketones. The broad substrate scopes and use of an inexpensive copper catalyst and green molecular oxygen as an oxidant as well as an O-source make this protocol very attractive for potential synthetic applications. The control experiments reveal that the present copper-catalyzed oxidative C-C bond cleavage of simple ketones proceeds in a novel catalytic pathway rather than through the cleavage of a dioxetane intermediate.