Alternative Synthetic Methods for PEPPSI-Type Palladium Complexes

Alternative procedures are reported for the preparation of PEPPSI‐type palladium complexes (PEPPSI = pyridine‐enhanced precatalyst preparation stabilization and initiation) in good to excellent yields. One method involves the reaction of [(NHC)Pd(acac)Cl] complexes (NHC = N‐heterocyclic carbene, aca...

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Bibliographic Details
Published in:European journal of inorganic chemistry 2014-08, Vol.2014 (22), p.3600-3607
Main Authors: Green, Kerry-Ann, Maragh, Paul T., Abdur-Rashid, Kamaluddin, Lough, Alan J., Dasgupta, Tara P.
Format: Article
Language:English
Subjects:
Carbene li­gands
Carbenes
Infrared spectroscopy
Methods
NHC ligands
NMR
NMR spectroscopy
Nuclear magnetic resonance
Palladium
Pyridines
Spectrum analysis
Stabilization
Synthesis design
X rays
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Summary:Alternative procedures are reported for the preparation of PEPPSI‐type palladium complexes (PEPPSI = pyridine‐enhanced precatalyst preparation stabilization and initiation) in good to excellent yields. One method involves the reaction of [(NHC)Pd(acac)Cl] complexes (NHC = N‐heterocyclic carbene, acac = acetylacetonate) with hydrohalides (HX; X = Cl, Br, I) of pyridine or 2,6‐lutidine. Two other one‐pot syntheses involve Pd(acac)2, the azolium salt and pyridine hydrohalide (or 2,6‐lutidine hydrohalide). The complexes were obtained as moisture‐ and air‐stable solids and were characterized by 1H and 13C NMR spectroscopy, CHN analysis, and IR spectroscopy. The various synthetic procedures and the yields of the desired products are discussed. The X‐ray structure of [1‐(2,6‐diisopropylphenyl)‐3‐(2,4,6‐trimethylphenyl)imidazolin‐2‐ylidene]Pd(acac)Cl (4c) is also reported. Several PEPPSI‐type complexes (PEPPSI = pyridine‐enhanced precatalyst preparation stabilization and initiation) were successfully prepared in good yields by a new synthetic method involving hydrohalides of pyridine, azolium salts and palladium bisacetylacetonate.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.201402317