Bis(triphenylphosphine)palladium(II)phthalimide - an easily prepared precatalyst for efficient Suzuki-Miyaura coupling of aryl bromides

N M Chaignon, I J S Fairlamb, A R Kapdi, R J K Taylor, A C Whitwood

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)191-199
Number of pages9
JournalJournal of Molecular Catalysis A: Chemical
Volume219
Issue number2
DOIs
Publication statusPublished - 16 Sept 2004

Keywords

  • palladium
  • cross-coupling
  • biaryls
  • heteroaryls
  • catalysis
  • ACTIVE PALLADIUM CATALYSTS
  • PHENYLBORONIC ACID
  • C-C
  • ORGANIC ELECTROPHILES
  • ARYLBORONIC ACIDS
  • METAL-COMPLEXES
  • MILD CONDITIONS
  • HECK REACTION
  • CHLORIDES
  • BOND

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