Synthesis, structure and norbornene polymerization activity of a bulky β-diketiminato palladium(II) complex

Olson, Jeremy A.; Paulose, Tressia Alias Princy; Wennek, P.; Quail, J. Wilson; Foley, Stephen Ronan

doi:10.1016/j.inoche.2008.08.006

Cited by 12 publications

(9 citation statements)

References 15 publications

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“…The whole molecule has a ‘W’ shape with the bridging O atom present in the centre. The bond distances and the bond angles compare well with those of the reported β‐diketiminate complex [L 1 Pd(OAc)] …”

Section: Resultssupporting

confidence: 69%

“…In the present work, vinylidene β‐diketimine L 2 was employed to synthesize metal complexes. It has been reported that when an equimolar mixture of L 1 H and Pd(OAc) 2 is stirred, a β‐diketiminate Pd complex, [L 1 Pd(OAc)], is formed, in which the diketiminate ligand is monoanionic . Since there is no acidic proton in L 2 it is difficult to predict how it reacts with Pd(OAc) 2 but it is interesting to probe such a reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Ligating groups like ─CN, ─CHO, ─PPh 2 and ─NO 2 have been integrated into the β‐diketimine ligand, resulting in the alteration of its coordination mode and/or its donor ability towards metals . Monoanionic β‐diketiminate and neutral β‐diketimine complexes of transition metals such as Fe, Co, Ni, Cu, Zn and Pd have been widely used in organic synthesis for the construction of natural products, biologically significant molecules and polymers through C─C bond formation. Among these methodologies, the Heck coupling reaction is a very convenient method to carry out C─C coupling between aryl halides and olefins.…”

Section: Introductionmentioning

confidence: 99%

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Pd and Ni complexes of a novel vinylidene β‐diketimine ligand: Their application as catalysts in Heck coupling and alkyne trimerization

Raghavendra

Nareddula

2017

Applied Organom Chemis

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A β-diketimine ligand with vinylidene substitution at γ-carbon, CH 2 C(CH 3 CNAr) 2 (Ar = 2,6-diisopropylphenyl) (L 2 ), was synthesized by treating β-diketimine H 2 C(CH 3 CNAr) 2 with n-BuLi followed by paraformaldehyde. L 2 formed the homobimetallic ether-bridged β-diketiminate complex [O{(CH 2 -β-diketiminate) Pd(OAc)} 2 ] (1) with (PdOAc) 2 . It also gave complexes [L 2 PdCl 2 ] (2) and [L 2 NiBr 2 ] (3) when treated with PdCl 2 (CH 3 CN) 2 and NiBr 2 (dimethoxyethane), respectively. All the compounds were characterized using 1 H/ 13 C NMR spectroscopy and single-crystal X-ray diffraction studies. The catalytic activity of Pd and Ni complexes 1, 2 and 3 was explored in Heck coupling and alkyne trimerization reactions and it was found that they are very good catalysts. The results are reported in detail.

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Section: Resultssupporting

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Pd and Ni complexes of a novel vinylidene β‐diketimine ligand: Their application as catalysts in Heck coupling and alkyne trimerization

Raghavendra

Nareddula

2017

Applied Organom Chemis

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“…Our results present rare examples of such insertion chemistry in Pd(II) complexes with a monoanionic, bidentate nitrogen ligand. 17,31…”

Section: Resultsmentioning

confidence: 99%

Palladium alkyl complexes with a formazanate ligand: synthesis, structure and reactivity

et al. 2018

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Palladium(ii) complexes with a bidentate, anionic formazanate ligand are described. Attempts to prepare mono(formazanate) palladium alkyl complexes often leads to the homoleptic bis(formazanate) complex, which shows rich electrochemistry due to the redox-active nature of the ligands. Performing salt metathesis between the precursor [Pd(COD)(CH3)Cl] and the potassium salt of the ligand in the presence of tetrabutylammonium chloride yields a square planar mono(formazanate) palladate complex through coordination of chloride anion. Ligand exchange allows binding of unsaturated molecules and evaluation of the reactivity of the Pd-CH3 fragment. Using this approach, insertion reactions of CO, isocyanide and methyl acrylate into the Pd-CH3 bond are demonstrated.

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“…Unlike most acetate‐bridged dinuclear palladium complexes, 1 and 2 are mononuclear complexes with a η 2 ‐acetate ligand. This might result from the steric hindrance of the substituents on the anilido groups 1k,1w. The Pd–N oxazoline [1.972(2) for 1 , 1.974(2) Å for 2 ] and Pd–N anilido bonds [1.9578(19) for 1 , 1.9675(19) Å for 2 ] are shorter than those found in structurally related palladium anilido‐oxazolinate complexes [Pd–N oxazoline 2.0254(14)–2.0731(13) Å; Pd–N anilido 1.9942(13)–2.0077(14) Å]5c,5f and close to those found in palladium β‐diketiminatecomplexes [Pd–N 1.958(4)–2.1113(7) Å] [1j,1k,1u–1z] and palladium anilidoiminate complexes [Pd–N imine 1.931–2.086(2) Å; Pd–N anilido 1.938(3)–2.109(3) Å] 6.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural Studies, and Catalytic Application of Palladium Complexes Containing Anilido‐Oxazolinate Ligands

Peng

Chen

2011

Eur J Inorg Chem

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A series of palladium anilido-oxazolinate complexes 18 prepared from ligand precursors HNArOxa [ortho-C6H4(NHAr)(4,4-dimethyl-2-oxazoline) where Ar = 2,4,6-trimethylphenyl, HNPhTriMeOxa; 2,6-diisopropylphenyl, HNPhDiiPrOxa; phenyl, HNPhHOxa; 2-methoxyphenyl, HNPhOMeOxa; 2-methylthiophenyl, HNPhSMeOxa] is reported. Treatment of HNArOxawith 1.1 equiv. Pd(OAc)2 afforded palladium(II) acetate complexes (NPhTriMeOxa)Pd(?2-OAc) (1) and (NPhDiiPrOxa)Pd(?2-OAc) (2) as monomeric complexes, [(NPhHOxa)Pd(OAc)]2 (3) as an anilido-bridged dinuclear complex, [(NPhOMeOxa)Pd(OAc)]2 (4) as an acetate-bridged dinuclear complex, and (NPhSMeOxa)Pd(OAc) (5) as a monomeric complex. The reactions of 2, 4, and 5 with an excess of NaCl(aq.) in acetone yielded palladium(II) chloride complexes, [(NPhDiiPrOxa)Pd(Cl)]2 (6) as a chloro-bridged dinuclear complex, (NPhOMeOxa)Pd(Cl) (7) as a monomeric complex, [(NPhOMeOxa)Pd(Cl)]2 (7') as an anilido-bridged dinuclear complex, and (NPhSMeOxa)Pd(Cl) (8) as a monomeric complex. The crystal and molecular structures of 18 are reported, and their application towards Suzuki and Heck reactions with a wide range of aryl halides has been examined

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Synthesis, structure and norbornene polymerization activity of a bulky β-diketiminato palladium(II) complex

Cited by 12 publications

References 15 publications

Pd and Ni complexes of a novel vinylidene β‐diketimine ligand: Their application as catalysts in Heck coupling and alkyne trimerization

Pd and Ni complexes of a novel vinylidene β‐diketimine ligand: Their application as catalysts in Heck coupling and alkyne trimerization

Palladium alkyl complexes with a formazanate ligand: synthesis, structure and reactivity

Synthesis, Structural Studies, and Catalytic Application of Palladium Complexes Containing Anilido‐Oxazolinate Ligands

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