Synthesis and characterization of triphenylphosphine adducts of ferrocene-based palladacycles and their performance in the Suzuki and Sonogashira reactions with bromo- and chloroarenes.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Su-Zhen BaiWei-Jun Fu

Abstract

A new triphenylphosphine adduct of cyclopalladated ferrocenylpyridazine containing a chloride anion, 2a, has been synthesized from the reaction of the chloride-bridged palladacyclic dimer 1a with triphenylphosphine. The corresponding adducts 3a,b containing iodide anion have been readily prepared through anion exchange reactions of 2a,b with NaI in acetone. These complexes were characterized by elemental analysis, IR and 1H-NMR. Additionally, their crystal structures have been determined by X-ray diffraction and intermolecular C-H···X (Cl, Br, I) bonds were found in the crystals. The use of these palladacycles as catalysts for the Suzuki and Sonogashira reactions was examined. The complexes 2a,b exhibited higher catalytic activity than the corresponding 3a,b in the Suzuki reaction. However, the order of activity of adducts with varying halogen anions is 3a~3b > 2a~>2b in the Sonogashira reaction.

References

Aug 23, 2003·Chemical Communications : Chem Comm·Robin B Bedford
Oct 10, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Chen XuYang-Jie Wu
Feb 20, 2007·Chemical Reviews·Rafael Chinchilla, Carmen Najera
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jun 15, 2010·Chemical Society Reviews·Diego A Alonso, Carmen Nájera
Jun 10, 2011·Chemical Society Reviews·Rafael Chinchilla, Carmen Nájera

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Citations

Jun 25, 2013·Chemical Reviews·Rafael Chinchilla, Carmen Nájera

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Methods Mentioned

BETA
X-ray

Software Mentioned

97
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