Pd-Catalyzed 1,4-Carboamination of Bromoarenes with Diazo Compounds and Amines

A palladium-catalyzed 1,4-carboamination of bromoarenes with diazo compounds and amines was developed. This reaction proceeds through a palladium-carbene that then generates a π-benzylpalladium intermediate, forming ipso C–C and para C–N bonds on haloarenes in a regioselective manner. The nature of this reaction as a multi-component reaction and its high regioselectivity can lead to a rapid construction of a range of para-substituted anilines. The successful application of this transformation to the rapid synthesis of an anti-tumor agent demonstrates its synthetic utility.