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Dalton Trans. 2015 Dec 07;44(45):19663-73. doi: 10.1039/c5dt02258d. Epub 2015 Sep 16.

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

Dalton transactions (Cambridge, England : 2003)

V Kolaříková, O Šimůnek, M Rybáčková, J Cvačka, A Březinová, J Kvíčala

Affiliations

  1. Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic. [email protected].

PMID: 26374142 DOI: 10.1039/c5dt02258d

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.

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