Copper-catalyzed rearrangement of oximes into primary amides

The atom-efficient and cost-effective rearrangement of oximes into primary amides is catalyzed by simple copper salts. The use of homogeneous Cu(OAc)2 (1-2 mol %) was found to be effective for this transformation at 80 °C. The reaction was successful with either conventional or microwave heating. CuO and CuO/ZnO on activated carbon provided a competent reuseable heterogeneous catalyst which could be used in a batch process or in flow. Copper salts are much cheaper than the precious metals previously used for this rearrangement, and the reaction conditions are milder than those reported.