Palladium-Catalyzed <i>N</i>‑Arylation of Cyclopropylamines

Abstract

A general method has been developed for the previously challenging arylation of cyclopropyl­amine and <i>N</i>-arylcyclo­propyl­amines. Highly active, air-stable, and commercially available R-allylpalladium precatalysts provide access to a wide range of (hetero)­arylated cyclo­propyl­anilines in high yields. Precatalysts [(<i>t</i>BuBrettPhos)­Pd­(allyl)]­OTf and [(BrettPhos)­Pd­(crotyl)]­OTf, deliver monoarylated products, while (P<i>t</i>Bu₃)­Pd­(crotyl)Cl is suited for preparing unsymmetrical diarylated products. The developed conditions tolerate a range of functional groups and heterocycles, allowing access to an array of arylated cyclopropylamines, a motif present in prominent drug molecules