Bis(triphenylphosphine)palladium(II)phthalimide – an easily prepared precatalyst for efficient Suzuki–Miyaura coupling of aryl bromides
作者:Nicholas M. Chaignon、Ian J.S. Fairlamb、Anant R. Kapdi、Richard J.K. Taylor、Adrian C. Whitwood
DOI:10.1016/j.molcata.2004.05.008
日期:2004.9
In this paper we report the synthesis and application of a novel palladium(II) complex, bis(triphenylphosphine)palladium(II)phthalimide 1. Its utility in the Suzuki-Miyaura coupling of aryl bromides with a variety of aryl- and heteroarylboronic acids, under relatively mild conditions, is described. Complex 1 is easily prepared from tetrakis(triphenylphosphine)palladium(0) and phthalimide in 78% yield and is air, light and moisture stable. On following the kinetics of the cross-coupling reaction of 4-nitro-1-bromobenzene with phenylboronic acid, mediated by 1 (1 mol%) in THF/aqueous 1 M NaCO3 (1/1, v/v) at 60degreesC, an initial induction period is observed, indicating that 1 is a precatalyst. The described work extends on our recent finding that 'imidate' type ligands have an influence in palladium-catalysed cross-coupling processes. (C) 2004 Elsevier B.V. All rights reserved.