Tsuji–Trost allylations with palladium recovery by phosphines/Pd(0)-triolefinic macrocyclic catalysts

Serra‐Muns, Anna; Pleixats, Roser

doi:10.1016/j.jorganchem.2010.01.033

Cited by 15 publications

(7 citation statements)

References 60 publications

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“…1) as a green reactant and solvent produces cinnamyl methyl carbonate (product I), a valuable carbonate ester, as the main and the desired compound with some amounts of the side products [4]. Carbonate ester finds its application as an allylic electrophile affording the alkylated products in organic synthesis, namely the Tsuji-Trost reaction and asymmetric allylic substitution [5][6][7]. At the same time cinnamyl methyl carbonate can be utilized for phenol group protection [8] and used in synthesis of biologically active compounds [7,9,10].…”

Section: Introductionmentioning

confidence: 99%

Carboxymethylation of cinnamylalcohol with dimethyl carbonate over the slag-based catalysts

Kholkina

Kumar

Eränen

et al. 2021

Reac Kinet Mech Cat

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The carboxymethylation of cinnamylalcohol with dimethyl carbonate was performed using low-cost catalysts obtained from desulfurization slag. Processing of steel slag performed by different techniques was resulted in a wide range of the catalysts with different morphological and structural properties. Catalytic evaluation of the slag catalysts illustrated diversity of the obtained results strongly dependent on the surface area, crystal morphology and basicity. Catalytic materials demonstrated high variability of the conversion (8–85%) exhibiting similar selectivity to the desired product – cinnamyl methyl carbonate (ca. 80%). A significant impact of ultrasonication on catalytic activity was observed. Comparison of the synthesized samples with commercial basic materials illustrated competitive ability of the slag catalysts. Based on the results of catalytic evaluation and product analysis the reaction network was proposed and verified by thermodynamic analysis. A kinetic model was developed to describe concentration dependencies in carboxymethylation.

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Section: Introductionmentioning

confidence: 99%

Carboxymethylation of cinnamylalcohol with dimethyl carbonate over the slag-based catalysts

Kholkina

Kumar

Eränen

et al. 2021

Reac Kinet Mech Cat

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“…The exocyclic double bond in the 3-position of the 1,5,9-triazacyclododecane ring, which is important for activity, enables an alternate macrocyclization strategy involving double N -allylation, as shown in Scheme (method B). Tsuji–Trost − N -allylation is well-precedented, − and hydroxyl groups in erythromycin A and other macrolide antibiotics have been bridged with an isobutylene unit by palladium-catalyzed reaction with 3-methylene-1,3-propanediyl bis( t -butylcarbonate) in THF or toluene. − In addition, palladium-catalyzed C -allylation with similar dielectrophiles has been used in natural product total syntheses. , …”

Section: Introductionmentioning

confidence: 99%

Tsuji–Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines

Ali

Anugu²,

Chawla

et al. 2019

ACS Omega

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Macrocyclic triamine disulfonamides can be synthesized by double Tsuji–Trost N-allylation reaction of open-chain disulfonamides with 2-alkylidene-1,3-propanediyl bis(carbonates). The previously used Atkins–Richman macrocyclization method generally gives lower yields and requires more tedious purification of the product. Solvent, palladium source, ligand, and concentration have all been varied to optimize the yields of two key 12-membered ring bioactive compounds, CADA and VGD020. The new approach tolerates a wide range of functional groups and gives highest yields for symmetrical compounds in which the acidities of the two sulfonamide groups are matched, although the yields of unsymmetrical compounds are still generally good. The method has also been extended to the synthesis of 11-membered rings, pyridine-fused macrocycles, and products bearing an ester or aryl substituent on the exocyclic double bond.

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“…The 15-membered triolefinic macrocycle (MAC), possessing excellent oxidation-resistant property and insolubility of alcohols, is a suitable electron donor for transition metals and easily removed from the reaction system [ 20 ]. Therefore, bimetallic DSNs with high stability, easy-removal and favourable catalytic activity and selectivity can be obtained [ 21 ], which will be a promising research field for the catalytic hydrogenation of unsaturated compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and hydrogenation application of Pt–Pd bimetallic nanocatalysts stabilized by macrocycle-modified dendrimer

et al. 2017

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Different generations of poly(propylene imine) (Gn-PPI) terminated with N-containing 15-membered triolefinic macrocycle (GnM) (n = 2, 3, 4, 5) were prepared. The bimetallic nanoparticle catalysts GnM-(Ptx/Pd10−x) (x = 0, 3, 5, 7, 10) were prepared by the synchronous ligand-exchange reaction between GnM and the complexes of Pt(PPh3)4 and Pd(PPh3)4. The structure and catalytic properties of GnM-(Ptx/Pd10−x) were characterized via Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance spectroscopy, X-ray diffraction, X-ray photoelectron spectroscopy, high-resolution transmission electron microscopy, energy-dispersive spectroscopy and inductively coupled plasma atomic emission spectroscopy. The novel bimetallic Pd–Pt nanoparticle catalysts stabilized by dendrimers (DSNs) present higher catalytic activities for the hydrogenation of dimeric acid (DA) than that of nitrile butadiene rubber (NBR). It can be concluded that bimetallic Pd–Pt DSNs possess alloying and synergistic electronic effects on account of the hydrogenation degree (HD) of DA and NBR. Furthermore, the HD of DA and NBR shows a remarkable decrease with the incremental generations (n) of GnM-(Pt3/Pd7) (n = 2, 3, 4, 5).

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Tsuji–Trost allylations with palladium recovery by phosphines/Pd(0)-triolefinic macrocyclic catalysts

Cited by 15 publications

References 60 publications

Carboxymethylation of cinnamylalcohol with dimethyl carbonate over the slag-based catalysts

Carboxymethylation of cinnamylalcohol with dimethyl carbonate over the slag-based catalysts

Tsuji–Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines

Synthesis and hydrogenation application of Pt–Pd bimetallic nanocatalysts stabilized by macrocycle-modified dendrimer

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