Synthesis of Biphenyl-Based Arsine Ligands by Suzuki-Miyaura Coupling and their Application to Pd-Catalyzed Arsination

PAULA M. UBERMAN; MARIO N. LANTERI; SOL C. PARAJÓN PUENZO ; SANDRA E. MARTÍN

DALTON TRANSACTIONS

ROYAL SOC CHEMISTRY

Año: 2011 vol. 40 p. 9229 - 9237

1477-9226

A versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands including first the Pd-catalyzed arsination to introduce the -AsPh2 moiety, and then the Suzuki-Miyaura cross-coupling for biaryl construction is reported. By the Pd-catalyzed arsination with n-Bu3SnAsPh2 (1), the (2-bromophenyl)diphenylarsine (2, 83%) was obtained. The Suzuki-Miyaura reaction between bromoarsine 2 and aryl boronic acids bearing different substituents provided biarylarsine ligands (80-99%). The efficiency of catalysts derived from the new biarylarsine ligands was evaluated in the Pd-catalyzed arsination with perfluoroalkyl iodides (RfI). Outstanding activities of catalysts derived from Pd/methoxybiarylarsine ligands were found in this coupling reaction affording perfluoroalkyl arsines in very good yields (57-100%).