Bifunctional N-Heterocyclic Carbene Ferrocenyl Ligands - Synthesis and Palladium(II) Complexes

• Published in: European journal of inorganic chemistry Vol. 2015; no. 4; pp. 609 - 616
• Main Authors: Loxq, Pauline, Daran, Jean-Claude, Manoury, Eric, Poli, Rinaldo, Labande, Agnès
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.02.2015; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc; Wiley-VCH Verlag
• Subjects: Carbene ligands; Carbenes; Cationic; Chemical Sciences; Chemistry; Chemistry, Inorganic & Nuclear; Coordination chemistry; Ferrocenes; Ligands; Mass spectrometry; N ligands; NMR; NMR spectroscopy; Nuclear magnetic resonance; Palladium; Physical Sciences; Precursors; Science & Technology; Synthesis; TRANSITION-METAL COMPLEXES; CRYSTAL-STRUCTURE; Ferrocenes; ARYLATION; REACTIVITY; COORDINATION; Palladium; Carbene ligands; N ligands; PD; NHC LIGANDS; EFFICIENT; ARYL CHLORIDES; CATALYSTS
• ISSN: 1434-1948; 1099-0682
• DOI: 10.1002/ejic.201403001

Two ferrocenylimidazolium tetrafluoroborate salts [R = Me, 7 and R = (2,4,6‐trimethylphenyl), 8], precursors of new ferrocenylimidazol‐2‐ylidene bifunctional ligands, have been prepared for the first time. The free 1‐(2‐dimethylaminomethyl)ferrocenyl‐3‐methylimidazol‐2‐ylidene (12) was isolated and characterised by 1H and 13C NMR spectroscopy and represents the second example of an isolated and characterised imidazol‐2‐ylidene directly linked to ferrocene. Neutral (compound 13) and cationic (compound 14) palladium(II) complexes were obtained in moderate yields and characterised by 1H and 13C NMR spectroscopy and mass spectrometry. Two ferrocenylimidazolium tetrafluoroborate salts, precursors of new ferrocenylimidazol‐2‐ylidene bifunctional ligands, and the corresponding palladium(II) complexes have been prepared for the first time.