Azo-amide palladium(II) complexes: Synthesis, characterization and application in C–C cross-coupling reactions

Jahar Lal Pratihar*, Paritosh Mandal, Chia Her Lin, C. K. Lai, Dasarath Mal

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

The newly designed tridentate ligands bis-2,2′-(N-alkylamino)azobenzene, 1a-1d, have been prepared by the reaction between 2,2′-diaminoazobenzene and alkyl halides in the presence of K2CO3. These ligands were reacted with Na2[PdCl4] in a 1:1 ratio in methanol to give the new Pd(II) complexes 2a–2d. All the compounds were characterized by 1H NMR, IR spectroscopy and elemental analysis. Furthermore, the solid-state structures of the ligand 1a and two complexes (2a and 2c) were determined using single crystal X-ray diffraction analysis. The diffraction analysis revealed that the ligands bind with the Pd(II) ion in a monoanionic tridentate (N,N,N) fashion, offering a distorted square planar geometry where the fourth position is occupied by one chloride ligand. The air/moisture stable complex 2a was employed as an efficient catalyst for the Suzuki and Heck reactions under mild conditions. The catalyst exhibits high catalytic activities for the coupling of several aryl halides with phenyl boronic acid and styrene, providing excellent yields. Further, the catalyst can be easily recovered by simple chromatographic separation and reused up to three times without significant loss of its catalytic activity.

Original languageEnglish
Pages (from-to)224-230
Number of pages7
JournalPolyhedron
Volume135
DOIs
Publication statusPublished - 2017
Externally publishedYes

Keywords

  • Bis-2,2′-(N-alkylamino)azobenzene
  • Catalysis
  • Crystal structure
  • Palladium(II)
  • Suzuki and Heck reaction

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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