Ligand-dependent stereoselective Suzuki-Miyaura cross-coupling reactions of β-enamido triflates

Abstract

The stereoselective Suzuki-Miyaura cross-coupling of (Z)-β-enamido triflates is demonstrated. Depending on the nature of the ligand in the palladium catalyst, either retention or inversion of the configuration during the synthesis of β,β-diaryl-substituted enamides is observed. Thus, the method provides synthetic access to both isomers of the target enamides from (Z)-β-enamido triflates.

Keywords: Suzuki–Miyaura coupling; enamides; isomerization; vinyl triflates.