Effective palladium(II)-bis(oxazoline) catalysts: Synthesis, crystal structure, and catalytic coupling reactions

Mansur B. Ibrahim, S. M. Shakil Hussain, Atif Fazal, Mohammed Fettouhi, Bassam El Ali*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

New bis(oxazoline) ligands and their palladium complexes were synthesized and characterized. X-ray crystal structures of the two new complexes showed distorted square planar geometry with the palladium ion bonded to nitrogens of two bidentate heterocycles in addition to two bromides and two acetate ions for Pd-BOX-1 and Pd-BOX-2, respectively. The complexes adopt a chair structure with a rigid curvature inducing an inherent chirality. The complexes were effective catalysts for Suzuki-Miyaura, Mizoroki-Heck, and copper-free Sonogashira coupling reactions in aqueous dimethylformamide and under aerobic conditions. The reaction conditions were optimized for best solvent, base, and temperature. The substrate scope of the new catalytic system was evaluated for coupling reactions of a variety of aryl halides with aryl boronic acids, alkenes, and alkynes.

Original languageEnglish
Pages (from-to)432-448
Number of pages17
JournalJournal of Coordination Chemistry
Volume68
Issue number3
DOIs
StatePublished - 1 Feb 2015

Bibliographical note

Publisher Copyright:
© 2015 Taylor and Francis.

Keywords

  • Bis(oxazoline)
  • Crystal structure
  • Mizoroki-Heck
  • Palladium
  • Sonogashira
  • Suzuki-Miyaura

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Chemistry

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