Abstract
Enantiomerically pure chelating NHC-isobornylamide 1 was prepared and reacted with palladium and platinum salts. This gave monodentate complexes with carbonate (Pd12CO3, 4), and chelating or monodentate complexes with acetylacetonate M1acac (M = Pd (5a), Pt (5b)) and M1(acac)2 (M = Pd (7a), Pt (7b)). This is in contrast to the reactions of the achiral NHC-cyclohexylamide derivative 2, which gave only chelating complexes (M2acac (M = Pd (6a), Pt (6b)). The reaction of 1 and 2 with Pd(allyl)Cl gave exclusively monodenate complexes 8 (Pd1(allyl)Cl) and 9 (Pd2(allyl)Cl). Several of the complexes were characterized structurally in the solid-state using X-ray crystallography, which showed that, when chelated, significant steric bulk of the chiral isobornyl group was directed towards the metal atom. This was also demonstrated in the formation of monodentate 7a and 7b, which showed E/Z isomerism of the amide bond. We were able to identify the major isomer as the Z-anti, with the minor isomer E-anti forming due to the hydrophobic nature of the isobornyl group and weak hydrogen bonding between the amide and acetylacetonate ligands.
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