The preparation of trans-2,5-dialkylpyrrolidinylbenzyldiphenylphosphines: new phosphinamine ligands for asymmetric catalysis

Cahill, John P.; Bohnen, Frank M.; Goddard, Richard; Guiry, Patrick J.

doi:10.1016/s0957-4166(98)00393-0

Cited by 37 publications

(20 citation statements)

References 19 publications

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“…For comparison, we synthesized a phosphine–amine complex of iridium(I), [Ir(P–NH 2 )(cod)]PF 6 ( 4 ), by the reaction of 2-(diphenylphosphino)benzylamine (P–NH 2 ) and [Ir(cod)Cl] 2 in the presence of a stoichiometric amount of AgPF 6 in a mixture of CH 2 Cl 2 and acetonitrile (CH 3 CN) solution (in a 6/1 ratio; Scheme ). This was also characterized by 1 H, 13 C{ 1 H}, and 31 P{ 1 H} NMR spectroscopy and an X-ray diffraction study (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Primary Amine Functionalized N-Heterocyclic Carbene Complexes of Iridium: Synthesis, Structure, and Catalysis

Lough

Morris

2013

Organometallics

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Always cite the published version, so the author(s) will receive recognition through services that track citation counts, e.g. Scopus. If you need to cite the page number of the author manuscript from TSpace because you cannot access the published version, then cite the TSpace version in addition to the published version using the permanent URI (handle) found on the record page. AbstractA square-planar iridium(I) complex [Ir(cod)(C-NH2)]PF6 (3·PF6) containing a primary amine based Nheterocyclic carbene ligand (C-NH2) ligand was synthesized by a transmetalation reaction of the nickel(II) complex 1, [Ni(C-NH2)2](PF6)2, with [Ir(cod)Cl]2 (cod = 1,5-cyclooctadiene). An addition reaction of HCl with 3·PF6 afforded a mixture of two isomers of the octahedral iridium(III) hydridochloride complex 5, IrHCl(cod)(C-NH2)PF6. One of the isomers, 5-cis-HCl, was found to have a rare geometry containing trans-H-Ir-NH2 and cis-H-Ir-Cl moieties. All of these iridium complexes were tested in the hydrogenation of unsaturated bonds. They are active catalysts in the H2-hydrogenation of acetophenone, with activity superior to a phosphine-amine (P-NH2) complex [Ir(cod)(P-NH2)]PF6 4, and half sandwich complexes [Ir(C5Me5)(C-NH2)Cl]PF6 (2a) and [Ir(C5H5)(C-NH2)Cl]PF6 (2b). Complex 3·PF6, however, was ineffective as a catalyst for the hydrogenation of trans--methylstilbene and N-(1-phenylethylidene)aniline.

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Section: Resultsmentioning

confidence: 99%

Primary Amine Functionalized N-Heterocyclic Carbene Complexes of Iridium: Synthesis, Structure, and Catalysis

Lough

Morris

2013

Organometallics

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“…Dioxane was dried with sodium metal and distilled under argon. phenyl]methylamine [20] was prepared by reduction of 2-(diphenylphosphino)benzonitrile [21]. Hdpf [12], [PdCl 2 (cod)] (cod = g 2 :g 2 -cycloocta-1,5-diene) [22], [PdCl(Me)(cod)] [23],…”

Section: Methodsmentioning

confidence: 99%

trans-Spanning ferrocene amidodiphosphine ligand: Synthesis, palladium complexes and catalytic use in Suzuki–Miyaura cross-coupling

Štěpnička

Krupa

Lamač

et al. 2009

Journal of Organometallic Chemistry

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“…of RuCp*(cod)Cl and subsequent workup in THF and toluene mixtures afforded crystallization of small amounts of [RuCp*(Z 6 -toluene)]PF 6 12 as a side product. Complex 3a was synthesized from the reaction of 2-(diphenylphosphino)benzylamine 13 and RuCp*(cod)Cl in dichloromethane. Subsequent halide abstraction with AgPF 6 and addition of excess pyridine at ambient temperature afforded a moderately oxygen-sensitive yellow solid in 67% yield (Scheme 1).…”

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confidence: 99%

The hydrogenation of molecules with polar bonds catalyzed by a ruthenium(ii) complex bearing a chelating N-heterocyclic carbene with a primary amine donor

2010

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The complex [RuCp*(C-NH(2))(py)]PF(6) bearing a chelating N-heterocyclic carbene with an NH(2) group (C-NH(2)) is an active catalyst for the H(2)-hydrogenation of ketones, an epoxide, ester and ketimine in basic solution. A maximum turnover frequency of 17,600 h(-1) is achieved under mild reaction conditions (25 °C) and economical use of hydrogen (8 bar) while the TOF of a related complex with a phosphine-amine ligand is much smaller.

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The preparation of trans-2,5-dialkylpyrrolidinylbenzyldiphenylphosphines: new phosphinamine ligands for asymmetric catalysis

Cited by 37 publications

References 19 publications

Primary Amine Functionalized N-Heterocyclic Carbene Complexes of Iridium: Synthesis, Structure, and Catalysis

Primary Amine Functionalized N-Heterocyclic Carbene Complexes of Iridium: Synthesis, Structure, and Catalysis

trans-Spanning ferrocene amidodiphosphine ligand: Synthesis, palladium complexes and catalytic use in Suzuki–Miyaura cross-coupling

The hydrogenation of molecules with polar bonds catalyzed by a ruthenium(ii) complex bearing a chelating N-heterocyclic carbene with a primary amine donor

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