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 AND SANDRA E. MARTÍN

DALTON TRANSACTIONS

ROYAL SOC CHEMISTRY

Año: 2011 vol. 2011 p. 9229 - 9237

1477-9226

A versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands, by a Pd-catalyzed arsination to introduce the -AsPh2 moiety, and then a Suzuki–Miyaura cross-coupling for biaryl construction is reported. By Pd-catalyzed arsination with n-Bu3SnAsPh2 (1), (2-bromophenyl)diphenylarsine (2, 83%) was obtained. The Suzuki–Miyaura reaction between the 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%).