Visible Light‐Mediated Copper(I)‐Catalysed Aerobic Oxidation of Ynamides/Ynamines at Room Temperature: A Sustainable Approach to the Synthesis of α‐Ketoimides/α‐Ketoamides

Abstract

Abstract A novel visible light‐mediated, copper‐catalysed aerobic oxidation of the C≡C bond in ynamides/ynamines at room temperature by using molecular oxygen as an oxidant is described. Overall, 23 examples were demonstrated with substrates having a wide range of functional groups. The current protocol can be readily scaled up to a preparative (1–2 g) scale with high yields (78–92%), high atom efficiency, and reaction mass efficiency. The mechanistic study shows that in‐situ formation of a copper(I)‐coordinated π‐complex ( λ max =460 nm) is most probably the key light absorbing species responsible for the visible light‐induced oxidation of ynamides and ynamines. This sustainable oxidation approach allows the direct synthesis of potentially important novel α‐ketoimide/α‐ketoamide skeletons without the need of external oxidants (organic/inorganic oxidants) and generation of stoichiometric amounts of wastes. magnified image