Cobalt-Catalyzed Decarboxylative Methylation and Ethylation of Aliphatic N -(Acyloxy)phthalimides with Organoaluminum Reagents.

A cobalt-catalyzed decarboxylative methylation of aliphatic redox-active esters [ N -(acyloxy)phthalimides; RAEs] with trimethylaluminum under mild conditions was developed, providing a method for transforming a carboxylate group into a methyl group without redox fluctuation. Primary and secondary RAEs were both amenable substrates, whereas a tertiary RAE delivered an elimination product. Triethylaluminum was also used to deliver a decarboxylative ethylation product. [ABSTRACT FROM AUTHOR]