An improved catalyst architecture for rhodium(III) catalyzed C-H activation and its application to pyridone synthesis

We have developed a method for preparing pyridones from the coupling reaction of acrylamides and alkynes with either stoichometric Cu(OAc)(2) or catalytic Cu(OAc)(2) and air as oxidants. In the course of these studies, it was found that a larger ligand, 1,3-di-tert-butylcyclopentadienyl (termed Cp-t) results in higher degrees of regioselectivity in the alkyne insertion event. The transformation tolerates a broad variety of alkynes and acrylamides. Furthermore, Cp-t and Cp* demonstrate similar catalytic activity. This similarity allows for mechanistic studies to be undertaken which suggest a difference in mechanism between this reaction and the previously studied benzamide system.