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Oxidative addition of N-halosuccinimides to palladium(0): The discovery of neutral palladium(II) imidate ligands, which enhance Stille coupling of allylic and benzylic halides

Crawforth, C.M., Burling, S., Fairlamb, I.J.S., Kapdi, A.R., Taylor, R.J.K. and Whitwood, A.C. (2005) Oxidative addition of N-halosuccinimides to palladium(0): The discovery of neutral palladium(II) imidate ligands, which enhance Stille coupling of allylic and benzylic halides. Tetrahedron, 61 (41). pp. 9736-9751. ISSN 0040 4020

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Abstract

The Stille coupling of organostannanes and organohalides, mediated by air and moisture stable palladium(II) phosphine complexes containing succinimide or phthalimide (imidate) ligands, has been investigated. An efficient synthetic route to several palladium(II) complexes containing succinimide and phthalimide ligands, has been developed. cis-Bromobis(triphenylphosphine)(N-succinimide)palladium(II) [(Ph3P)2Pd(N-Succ)Br] is shown to mediate the Stille coupling of allylic and benzylic halides with alkenyl, aryl and allyl stannanes. In competition experiments between 4-nitrobromobenzene and benzyl bromide with a cis-stannylvinyl ester, (Ph3P)2Pd(N-Succ)Br preferentially cross-couples benzyl bromide, whereas with other commonly employed precatalysts 4-nitrobromobenzene undergoes preferential cross-coupling. Furthermore, preferential reaction of deactivated benzyl bromides over activated benzyl bromides is observed for the first time. The type of halide and presence of a succinimide ligand are essential for effective Stille coupling. The type of phosphine ligand is also shown to alter the catalytic activity of palladium(II) succinimide complexes.

Item Type: Article
Academic Units: The University of York > Chemistry (York)
Depositing User: York RAE Import
Date Deposited: 04 Mar 2009 16:45
Last Modified: 04 Mar 2009 16:45
Published Version: http://dx.doi.org/10.1016/j.tet.2005.06.080
Status: Published
Publisher: Elsevier Science B.V., Amsterdam.
Identification Number: 10.1016/j.tet.2005.06.080
URI: http://eprints.whiterose.ac.uk/id/eprint/7588

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