Exploring the reactivity of (hetero)aryl amides in the Chan-Evans-Lam reaction with arylalkenyl boron reagents

Abstract

The unique reactivity and stability of enamides make them attractive reagents in organic synthesis. Herein, we investigated the reactivity of acetanilides and pyridyl acetamides in the formation of a C–N bond through a Chan-Evans-Lam reaction using arylalkenyl boron-based reagents yielding a wide scope of N-aryl enamides with an E configuration. The products obtained have been applied in the synthesis of N-heterocycles, an important scaffold in several biologically active compounds, via sequential Heck reaction to prove the practical utility of the prepared N-aryl enamides.