Design and Synthesis of Dialkylarylphosphine Urea Ligands and their Application in Palladium-Catalyzed Cross-Coupling Reactions

We describe herein the design and synthesis of a new class of dialkylarylphosphine ligands incorporating a Lewis-basic urea subunit. The ligand synthesis consisted of six linear steps and was enabled by the discovery of a new N-to-N alkyl migration reaction. This new series of dialkylarylphosphine urea ligands were applied in common palladium-catalyzed cross-coupling reactions for the formation of carbon-carbon and carbon-nitrogen bonds in moderate to high yields. The design and synthesis of a new class of dialkylarylphosphine urea ligands. Published in @HelvChimActa for their special #Denmark_Issue dedicated to Prof. Scott E. Denmark on the occasion of his 70th birthday.+ image