NH⋯O and NH⋯N Hydrogen Bonded Networks in Imidazole-Based Phosphane Oxides: Structures of Tris(2-Isopropylimidazol-4(5)-yl)Phosphane Oxide, Bis(2-Isopropylimidazol-4(5)-yl)Phosphane Oxide and Diphenyl-2-Isopropylimidazol-4(5)-yl Phosphane Oxide

A variety of piano-stool complexes of cyclopentadienyl ruthenium(II) with imidazole-based PN ligands have been synthesized starting from the precursor complexes CpRu(C10H8)]PF6, CpRu(NCMe)(3)]PF6 and CpRu(PPh3)(2)Cl]. PN ligands used are imidazol-2-yl, -4-yl and -5-yl phosphines. Depending on the ligand and precursor different types of coordination modes were observed; in the case of polyimidazolyl PN ligands these were kappa P-1-monodentate, kappa P-2,N-, kappa N-2,N-and kappa N-3,N,N-chelating and mu-kappa P:kappa N-2,N-brigding. The solid-state structures of CpRu(1a)(2)Cl]center dot H2O (5 center dot H2O) and CpRu(mu-kappa(2)-N,N-kappa('1)-P-2b)(2)](C6H5PO3H)(2)(C6H5PO3H2)( 2), a hydrolysis product of the as well determined CpRu(2b) (2)](PF6)(2)center dot 2CH(3)CN (7b center dot 2CH(3)CN) were determined (1a = imidazol-2-yldiphenyl phosphine, 2b = bis(1-methylimidazol-2-yl) phenyl phosphine, 3a = tris(imidazol-2-yl) phosphine). Furthermore, the complexes CpRu(L) (2) [e] Anorganisch-Chemisches Institut, Universität Zürich-Irchel, Winterthurerstr. 190, CH-8057 Zürich, Switzerland.[ ‡] X-ray structure analysis.

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Gold(I) Catalysts with Bifunctional P, N Ligands

Wetzel

Kunz

Thiel

et al. 2011

Inorg. Chem.

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A series of phosphanes with imidazolyl substituents were prepared as hemilabile PN ligands. The corresponding gold(I) complexes were tested as bifunctional catalysts in the Markovnikov hydration of 1-octyne, as well as in the synthesis of propargylamines by the three component coupling reaction of piperidine, benzaldehyde, and phenylacetylene. While the activity in the hydration of 1-octyne was low, the complexes are potent catalysts for the three component coupling reaction. In homogeneous solution the conversions to the respective propargylamine were considerably higher than under aqueous biphasic conditions. The connectivity of the imidazolyl substituents to the phosphorus atom, their substitution pattern, as well as the number of heteroaromatic substituents have pronounced effects on the catalytic activity of the corresponding gold(I) complexes. Furthermore, formation of polymetallic species with Au(2), Au(3), and Au(4) units has been observed and the solid-state structures of the compounds (5)(2)Au(3)Cl(2)]Cl and (3c)(2)Au(4)Cl(2)]Cl(2) (3c = tris(2-isopropylimidazol-4(5)-yl phosphane, 5 = 2-tert-butylimidazol-4(5)-yldiphenyl phosphane) were determined. The gold(I) complexes of imidazol-2-yl phosphane ligands proved to be a novel source for bis(NHC)gold(I) complexes (NHC = N-heterocyclic carbene). 1 Gold(I) catalysts with bifunctional P,N ligands Corinna Wetzel, [a] Peter C. Kunz,* [a] Indre Thiel, [a] Bernhard Spingler [b] [a] Institut für Anorganische Chemie und Strukturchemie I, Heinrich-Heine Universität Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany. Fax: (+)49 211 8112287; E-mail:peter.kunz@uni-duesseldorf.de.

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NH⋯O and NH⋯N Hydrogen Bonded Networks in Imidazole-Based Phosphane Oxides: Structures of Tris(2-Isopropylimidazol-4(5)-yl)Phosphane Oxide, Bis(2-Isopropylimidazol-4(5)-yl)Phosphane Oxide and Diphenyl-2-Isopropylimidazol-4(5)-yl Phosphane Oxide

Abstract: NH ... O and NH ... N hydrogen bonded networks in imidazole-based phosphane oxides: Structures of tris(2-isopropylimidazol-4(5)-yl)phosphane oxide, bis(2-isopropylimidazol-4(5)yl)phosphane oxide and diphenyl-2-isopropylimidazol-4(5)-yl phosphane oxide

Cited by 6 publications

References 21 publications

Synthesis and coordination chemistry of pyrimidine-substituted phosphine ligands

Synthesis and coordination chemistry of pyrimidine-substituted phosphine ligands

Ruthenium piano-stool complexes bearing imidazole-based PN ligands

Gold(I) Catalysts with Bifunctional P, N Ligands

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