Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons

Abstract

We here report a catalytic strategy to enable the decarboxylative allylic amination of vinyl cyclic carbonates using various aliphatic and nucleophilic amines. The use of a protic medium and chelating diphosphine ligands is a main driver towards chemo-selective allylic amine formation, thereby minimizing undesired ligand-driven complex speciation and aminolysis of the involved substrate. This improved approach amplifies the repertoire of allylic amine synthons that can be prepared from a variety of substrate combinations.