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Molecules 2012, 17(5), 5532-5543; doi:10.3390/molecules17055532

Synthesis and Characterization of Triphenylphosphine Adducts of Ferrocene-Based Palladacycles and Their Performance in the Suzuki and Sonogashira Reactions with Bromo- and Chloroarenes

1
College of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan, Henan 467002, China
2
College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan 471022, China
*
Author to whom correspondence should be addressed.
Received: 12 April 2012 / Revised: 3 May 2012 / Accepted: 4 May 2012 / Published: 9 May 2012
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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.
Keywords: adduct; palladacycle; crystal structure; Suzuki reaction; Sonogashira reaction adduct; palladacycle; crystal structure; Suzuki reaction; Sonogashira reaction
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Bai, S.-Z.; Xu, C.; Li, H.-M.; Wang, Z.-Q.; Fu, W.-J. Synthesis and Characterization of Triphenylphosphine Adducts of Ferrocene-Based Palladacycles and Their Performance in the Suzuki and Sonogashira Reactions with Bromo- and Chloroarenes. Molecules 2012, 17, 5532-5543.

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