Room-Temperature Pd-Catalyzed Amidation of Aryl Bromides Using tert-Butyl Carbamate

The scope of Pd-catalyzed synthesis of N-Boc-protected anilines from aryl bromides and commercially available tert-butyl carbamate is described. For the first time, this process can be conducted at room temperature (17−22 °C) using a combination of Pd2dba3·CHCl3 and a monodentate ligand, tert-butyl X-Phos. Use of sodium tert-butoxide is crucial to the success of the reaction, which proceeds in 43−83% yield.