Monodentate palladium complexes bearing abnormal and normal carbene ligands with a formally identical steric environment

Chun Hung Ke, Bing Chiuan Kuo, Debkumar Nandi, Hon Man Lee

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

We report a series of novel isomeric Pd(II) complexes with monodentate abnormal and normal carbene ligands, possessing a formally identical steric environment around the metal center. The corresponding ligand precursors were prepared via the key steps based on Pd-catalyzed direct C-H arylation between imidazo[1,2-a]pyridine and aryl bromides and Cu-catalyzed C-N coupling reactions between benzoimidazole and aryl bromides. The new complexes were characterized by 1D and 2D NMR spectroscopy, X-ray crystallography, and elemental analysis. The isomeric pairs of ligands show minor differences among their steric properties, which were examined by calculating their buried volume. The abnormal carbene Pd(II) complexes were found to be more efficient in catalyzing Mizoroki-Heck coupling, direct C-H arylation, and decarboxylative coupling reactions, which can be clearly attributed to a stronger electronic donating effect of the abnormal carbene ligands.

Original languageEnglish
Pages (from-to)4775-4784
Number of pages10
JournalOrganometallics
Volume32
Issue number17
DOIs
Publication statusPublished - 2013 Sep 9

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Bearings (structural)
Palladium
carbenes
palladium
Ligands
ligands
Bromides
bromides
X ray crystallography
Nuclear magnetic resonance spectroscopy
crystallography
pyridines
Metals
nuclear magnetic resonance
carbene
Chemical analysis
electronics
metals
spectroscopy
x rays

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Ke, Chun Hung ; Kuo, Bing Chiuan ; Nandi, Debkumar ; Lee, Hon Man. / Monodentate palladium complexes bearing abnormal and normal carbene ligands with a formally identical steric environment. In: Organometallics. 2013 ; Vol. 32, No. 17. pp. 4775-4784.
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Monodentate palladium complexes bearing abnormal and normal carbene ligands with a formally identical steric environment. / Ke, Chun Hung; Kuo, Bing Chiuan; Nandi, Debkumar; Lee, Hon Man.

In: Organometallics, Vol. 32, No. 17, 09.09.2013, p. 4775-4784.

Research output: Contribution to journalArticle

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AB - We report a series of novel isomeric Pd(II) complexes with monodentate abnormal and normal carbene ligands, possessing a formally identical steric environment around the metal center. The corresponding ligand precursors were prepared via the key steps based on Pd-catalyzed direct C-H arylation between imidazo[1,2-a]pyridine and aryl bromides and Cu-catalyzed C-N coupling reactions between benzoimidazole and aryl bromides. The new complexes were characterized by 1D and 2D NMR spectroscopy, X-ray crystallography, and elemental analysis. The isomeric pairs of ligands show minor differences among their steric properties, which were examined by calculating their buried volume. The abnormal carbene Pd(II) complexes were found to be more efficient in catalyzing Mizoroki-Heck coupling, direct C-H arylation, and decarboxylative coupling reactions, which can be clearly attributed to a stronger electronic donating effect of the abnormal carbene ligands.

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