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Transition metal complexes bearing NHC ligands substituted with secondary polyfluoroalkyl groups.

Dalton transactions (Cambridge, England : 2003) (2015-09-17)
V Kolaříková, O Šimůnek, M Rybáčková, J Cvačka, A Březinová, J Kvíčala
ABSTRACT

Using three different approaches, racemic 1-(perfluoroalkyl)ethylamines were synthesized from perfluoroalkyl iodides or perfluoroalkanoic acids, and further transformed to the corresponding N,N'-disubstituted ethane-1,2-diimines and ethane-1,2-diamines as mixtures of diastereoisomers. Their cyclization afforded imidazolium or dihydroimidazolium salts, which led to silver or palladium complexes bearing NHC ligands substituted with secondary polyfluoroalkyl groups. The palladium complexes bearing a throwaway 3-chloropyridine ligand proved to be moderately active in the model Suzuki-Miyaura coupling.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Toluene, anhydrous, 99.8%
Sigma-Aldrich
Diethyl ether, contains 1 ppm BHT as inhibitor, anhydrous, ≥99.7%
Sigma-Aldrich
Toluene, ACS reagent, ≥99.5%
Sigma-Aldrich
Diethyl ether, anhydrous, ACS reagent, ≥99.0%, contains BHT as inhibitor
Sigma-Aldrich
Diethyl ether, ACS reagent, anhydrous, ≥99.0%, contains BHT as inhibitor
Sigma-Aldrich
Phenylboronic acid, 95%
Sigma-Aldrich
Diethyl ether
Sigma-Aldrich
Perfluoroheptanoic acid, ≥97.0%
Sigma-Aldrich
4-Iodotoluene, 99%
Sigma-Aldrich
Perfluorohexyl iodide, 99%