Issue 36, 2011

Synthesis of biphenyl-based arsine ligands by Suzuki–Miyaura coupling and their application to Pd-catalyzed arsination

Abstract

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%).

Graphical abstract: Synthesis of biphenyl-based arsine ligands by Suzuki–Miyaura coupling and their application to Pd-catalyzed arsination

Supplementary files

Article information

Article type
Paper
Submitted
07 Feb 2011
Accepted
08 Jun 2011
First published
10 Aug 2011

Dalton Trans., 2011,40, 9229-9237

Synthesis of biphenyl-based arsine ligands by Suzuki–Miyaura coupling and their application to Pd-catalyzed arsination

P. M. Uberman, M. N. Lanteri, S. C. Parajón Puenzo and S. E. Martín, Dalton Trans., 2011, 40, 9229 DOI: 10.1039/C1DT10207A

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