The combination of a urea catalyst and an a-nitro-a-diazo ester gives rise to a reactive species able to undergo insertion into the N-H bonds of anilines. This new strategy to achieve N-H insertion reactivity is in contrast to typical metal-catalyzed conditions for the generation of carbenoids from alpha-diazocarbonyl compounds. This report includes the extension of the insertion reaction to a three-component coupling for the construction of alpha-amino-alpha-aryl esters in high yield.