Palladium-catalyzed synthesis of mixed anhydrides <i>via</i> carbonylative telomerization

A convenient and general palladium-catalyzed carbonylative coupling for the synthesis of 2-arylbenzoxazinones.

Benzoxazinones represent a class of annulated nitrogen heterocycles that are of interest to organic synthesis owing to their various biological activities. Among the different methodologies developed for their preparation, cyclization of anthranilic acid, N-acylanthranilic acid, or isotonic anhydride are most accepted. Although alternative methodologies are known, the availability of substrates...

Palladium-catalyzed carbonylative Sonogashira coupling between aryl triazenes and alkynes.

We developed a palladium-catalyzed carbonylative Sonogashira reaction with aryl triazenes and alkynes as substrates and methanesulfonic acid as the additive. A series of α,β-ynones were synthesized by this alternative procedure. Notably, bromides, iodides and hydroxyl groups could be well-tolerated under these reaction conditions.

Sc(OTf)3-catalyzed synthesis of anhydrides from twisted amides.

A novel synthesis of anhydrides from twisted amides is reported. Sc(OTf)3 catalysis in the presence of water is used to synthesize anhydrides in one step from amides without external nucleophiles. Mechanistic studies indicate that the coordination of the catalyst is critical to induce the challenging N-C activation step. This process further highlights the utility of twisted amides in organic s...

Palladium-catalyzed regioselective carbonylation of C-H bonds of N-alkyl anilines for synthesis of isatoic anhydrides.

A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety...

Palladium-catalyzed carbonylative Negishi-type coupling of aryl iodides with benzyl chlorides.