Urea Synthesis from Isocyanides and <i>O</i>-Benzoyl Hydroxylamines Catalyzed by a Copper Salt

Abstract

In the presence of CuOAc, a series of unsymmetric ureas can be generated in moderate to good yields under mild reaction conditions (10 mol% of CuOAc, 2 equiv t-BuONa or PhONa, 30 °C), using aryl isocyanides and O-benzoyl hydroxylamines as the readily accessible starting materials. The reactions might undergo a cascade process involving isocyanide insertion into the N-O bond and Mumm-type rearrangement. This work represents a rare example of isocyanide insertion into N-O bonds, which would extend isocyanide insertion chemistry.

Keywords

• copper catalysis
• isocyanides
• hydroxylamines
• ureas
• insertion