Highly efficient palladium-catalyzed arsination. Synthesis of a biphenyl arsine ligand and its application to obtain perfluoroalkylarsines

Abstract

An efficient one-pot, two-step Pd-catalyzed arsination with n-Bu 3SnAsPh2 (1) and sterically hindered aryl iodides (ArI) with different functional groups is reported. The cross-coupling reactions of this stannane with ArI afforded the functionalized triarylarsines in very good isolated yields (71-88%). By using this methodology, a biphenyl arsine ligand, AsPh2(bph), was achieved and its use as ligand in the Pd-catalyzed arsination with RfI to obtain perfluoroalkylarsines is also reported. In this reaction, the activity of a variety of phosphine and arsine ligands was investigated. The new biphenyl arsine ligand AsPh2(bph) proved to be the best one for the arsination reaction with RfI.