Organometallic chemistry of 15-membered tri-olefinic macrocycles: catalysis by palladium(0) complexes in carbon–carbon bond-forming reactions

Moreno‐Mañas, Marcial; Pleixats, Roser; Sebastián, Rosa Marı́a; Vallribera, Adelina; Roglans, Anna

doi:10.1016/j.jorganchem.2004.05.024

Cited by 48 publications

(12 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Some of us have previously described the preparation of 15‐membered triolefinic macrocycles 3 4 and their complexes with silver( I ), platinum(0), and in particular, palladium(0) 4 (Figure 2). 4, 5 Moreover, complexes 4 have been used as recoverable catalysts in Suzuki‐type cross‐couplings,4a,d,f,g, 6 telomerization of butadiene with methanol,7 hydroarylation of alkynes in ionic liquids,8 and the Mizoroki–Heck reaction 9…”

Section: Introductionmentioning

confidence: 99%

Structural Analysis of Chiral Complexes of Palladium(0) with 15‐Membered Triolefinic Macrocyclic Ligands

Pla‐Quintana

Roglans

Julián-Ortiz

et al. 2005

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

The complete structural analysis of the palladium complexes of the triolefinic macrocycles (E,E,E)-1,6,11-tris(arylsulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-trienes, which featured from three identical to three different aryl groups, was achieved by performing X-ray diffraction studies, NMR spectroscopy, and other calculations. The stereochemical complexity is determined by the different isomers formed through complexation of the metal to one or other face of each of the three olefins involved. The palladacyclopropane formulation of the palladium-olefin interaction offers a clear picture of the stereogenicity of the olefin carbon atoms that are complexed to the metal. The energetically favorable isomers were identified in the solid-state and in solution by performing X-ray diffraction and NMR spectroscopic analysis, respectively.

show abstract

Section: Introductionmentioning

confidence: 99%

Structural Analysis of Chiral Complexes of Palladium(0) with 15‐Membered Triolefinic Macrocyclic Ligands

Pla‐Quintana

Roglans

Julián-Ortiz

et al. 2005

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

show abstract

“…4 complexes through three endocyclic olefins. [9,11] Since the transfer of metals from Pd is composed of Pd and Pt elements, and the approximate Pd-to-Pt atomic ratio is 7.5:2.5, which is higher than the initial Pd(PPh 3 ) 4 -to-Pt(PPh 3 ) 4 addition molar ratio of 7:3 in the bimetallic transfer system. Figure 5 presents XPS scans of the Pd and Pt binding energy regions for the G3-M(Pd 7 Pt 3 ) DSNs.…”

Section: Periphery Modification Of G3-ppimentioning

confidence: 98%

“…[10] The double bonds in nitrogencontaining 15-membered triolefinic macrocyclic ligands are excellent electron donors for transition metal atoms; the macrocyclic ligands have higher antioxide stabilization and tend to coordinate with metal atoms to form complexes, which are beneficial for the stability and recovery of metal nanoparticles. [11] One can see that they might be applicable for the catalytic reactions of polymer substrate. However, there are few reports of macrocyclic complexes being used in processes for the catalytic hydrogenation of NBR.…”

Section: Introductionmentioning

confidence: 99%

Preparation, characterization and catalytic application of PdPt bimetallic nanoparticles stabilized by 15‐membered triolefinic macrocycle‐terminated poly(propylene imine) dendrimer

Zhou

Xiao-ran

Jin

et al. 2016

Applied Organom Chemis

View full text Add to dashboard Cite

PdPt bimetallic nanoparticles stabilized by 15-membered triolefinic macrocycle-stabilized poly(propylene imine) dendrimer (G3-M(Pd x Pt 10−x ) DSNs) have been prepared via synthesis of a 15-membered triolefinic macrocycle-modified third-generation poly(propylene imine) dendrimer (G3-M) and then synchronous ligand exchange with Pd(PPh 3 ) 4 /Pt(PPh 3 ) 4 complexes. The structure and catalytic activity of the DSNs were characterized using Fourier transform infrared, 1 H NMR, transmission electron microscopy, energy-dispersive X-ray and X-ray photoelectron analyses. As a novel catalyst system, it can be concluded that the composition of the bimetallic nanoparticles has an influence on the catalytic activity of the hydrogenation reaction of acrylonitrile-butadiene rubber, which can be related to synergistic effect. Furthermore, the selectivity and recyclability of G3-M(Pd x Pt 10−x ) DSN catalyst are also discussed.

show abstract

“…In a previous project in which we participated, synthetic routes towards 15-membered triazatrienic macrocycles were optimized [ 45 , 46 ]. This was our source of inspiration towards the synthesis of the array of triacetylenic macrocycles that have been prepared for testing in the [2+2+2] cycloaddition reaction, shown in Figure 1 .…”

Section: Synthesis Of Polyunsaturated Azamacrocyclesmentioning

confidence: 99%

[2+2+2] Cycloaddition Reactions of Macrocyclic Systems Catalyzed by Transition Metals. A Review

Pla‐Quintana

Roglans

2010

Molecules

Self Cite

View full text Add to dashboard Cite

Polyalkyne and enediyne azamacrocycles are prepared from arenesulfonamides and various alkyne and alkene derivatives either under basic or neutral conditions. The new family of macrocyclic substrates is tested in the [2+2+2] cycloaddition reaction. Several catalysts are used for the cycloisomerization reaction, and their enantioinduction is evaluated as appropriate. The effect of the structural features of the macrocycles, namely the ring size, substituents in precise positions and the number and type of unsaturations, on the [2+2+2] cycloaddition reaction has also been studied.

show abstract

Organometallic chemistry of 15-membered tri-olefinic macrocycles: catalysis by palladium(0) complexes in carbon–carbon bond-forming reactions

Cited by 48 publications

References 36 publications

Structural Analysis of Chiral Complexes of Palladium(0) with 15‐Membered Triolefinic Macrocyclic Ligands

Structural Analysis of Chiral Complexes of Palladium(0) with 15‐Membered Triolefinic Macrocyclic Ligands

Preparation, characterization and catalytic application of PdPt bimetallic nanoparticles stabilized by 15‐membered triolefinic macrocycle‐terminated poly(propylene imine) dendrimer

[2+2+2] Cycloaddition Reactions of Macrocyclic Systems Catalyzed by Transition Metals. A Review

Contact Info

Product

Resources

About