Highly Efficient Palladium-Catalyzed Arsination. Synthesis of a Biphenyl Arsine Ligand and Their Application to Obtained Perfluoralkylarsines

PAULA M. UBERMAN; MARIO N. LANTERI; SANDRA E. MARTÍN

ORGANOMETALLICS

American Chemical Society

Año: 2009 vol. 28 p. 6927 - 6934

0276-7333

An efficient one-pot, two-step Pd-catalyzed arsination with n-Bu3SnAsPh2 (1) and sterically hindered aryl iodides (ArI) is reported. The stannane n-Bu3SnAsPh2 was synthesized by the reaction of Ph2As- anion with n-Bu3SnCl. 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.