Michael Addition and Oxidative Cross‐Coupling Reaction of α‐Oxo Ketene Dithioacetals and Maleimides: Switchable Synthesis of 3‐Alkenyl Succinimides and Maleimides

Abstract

AbstractSwitchable synthesis of 3‐alkenyl succinimides and maleimides has been achieved via Michael addition and oxidative cross‐coupling reaction of α‐oxo ketene dithioacetals and maleimides by switching different reaction conditions. In the presence of 30 mol% of CH3SO3H in DCE at 120 °C, Michael addition reaction of α‐oxo ketene dithioacetals and maleimides occurred to afford 3‐alkenyl succinimides in 40–90% yields, whereas in the presence of 30 mol% of Pd(OAc)2 in DMF at 20 °C, 3‐alkenyl maleimides were obtained in 40–80% yields from the oxidative cross‐coupling reaction of α‐oxo ketene dithioacetals with maleimides. The presupposition of directing groups onto the substrates is not required in the Michael addition reaction. The method can be extended to gram scale.