Electrochemical bromination of enamides with sodium bromide

Abstract

The electrochemical bromination of enamide derivatives was developed using inexpensive and non-toxic sodium bromide (NaBr). This transformation enabled the direct stereoselective formation of a C(sp²)−Br bond and was applied to a wide variety of enamides without the need for external hazardous oxidants, reductants or metal catalysts. The protocol showed a general efficiency and tolerance, allowing access to brominated enamides with yields ranging from 56% to 85%. The reaction conditions were applied to the chlorination reaction using sodium chloride (NaCl). The synthetic utility of the products was illustrated through Suzuki and Sonogashira cross-coupling reactions, offering a novel reaction procedure to access complex enamide derivatives.