Copper catalyzed Heck-like cyclizations of oxime esters

Abstract

Copper catalyzed Heck-like cyclizations of oxime esters are described. Mechanistic studies indicate a reaction pathway that proceeds via the generation and cyclization of an intermediate that possesses iminyl radical character. To the best of our knowledge, this work encompasses the first examples of Cu-catalyzed aza-Heck reactions that proceed via oxidative initiation at nitrogen to generate products containing a new alkene. This new protocol is also an effective alternative to Pd-based systems and highlights the value of replacing precious metal catalysts with cheaper and more sustainable variants. This journal is © the Partner Organisations 2014.