Lanthanide-catalyzed deamidative cyclization of secondary amides and ynones through tandem C-H and C-N activation.

Abstract

The tandem inert α-C-H and C-N bond activation of amides represents a highly valuable but challenging transformation in organic synthesis. Herein, a simple rare earth metal amido complex has been shown to catalyse unprecedented cyclization of amides with ynones to form trisubstituted 2-pyrones. This protocol significantly enables the selective merger of inert α-C-H and C-N bond activations of amides and indicates a particular role of rare earth catalysts in enhancing the selectivity for the α-C-H bond of amides in the presence of N-H bonds.