Phenylation of Alkenyl Triflates: Reaction with Tetrabutylammonium Difluorotriphenylstannate.

Martı́nez, Antonio Garcı́a; Barcina, José Osío; Cerezo, Álvaro de Fresno; Subramanian, L. R.

doi:10.1055/s-1994-23081

Cited by 38 publications

(11 citation statements)

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“…As fluoride additives have been reported as ef- fective activators for this coupling reaction, [35] CsF was selected as the base. To achieve the optimized reaction conditions, several types of organic solvents and different reaction temperature were tested.…”

Section: Stille Coupling Reactionmentioning

confidence: 99%

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Air‐Stable and Highly Active Dendritic Phosphine Oxide‐ Stabilized Palladium Nanoparticles: Preparation, Characterization and Applications in the Carbon‐Carbon Bond Formation and Hydrogenation Reactions

Zhang

et al. 2008

Adv Synth Catal

109

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Dendrimer‐stabilized palladium nanoparticles were formed in the reduction of palldium bis(acetylacetonate) [Pd(acac)2] in the presence of phosphine dendrimer ligands using hydrogen in tetrahydrofuran. The resulting Pd nanoparticles were characterized by TEM, 31P NMR and 31P MAS NMR. The results indicated that the dendritic phosphine ligands were oxidized to phosphine oxides. These dendrimer‐stabilized Pd nanoparticles were demonstrated to be efficient catalysts for Suzuki and Stille coupling reactions and hydrogenations. The dendritic wedges served as a stabilizer for keeping the nanoparticles from aggregating, and as a vehicle for facilitating the separation and/or the recycling of the Pd catalyst. In the case of the Suzuki coupling reaction, these Pd nanoparticles exhibited high catalytic efficiency (TON up to 65,000) and air stability as compared with the commonly used homogeneous catalyst tetrakis(triphenylphosphine)palladium [Pd(PPh3)4]. In addition, the results obtained from the bulky dendritic substrate suggest that the Pd nanoparticles might act as reservoir of catalytically active species, and that the reaction is actually catalyzed by the soluble Pd(0) and/or Pd(II) species leached from the nanoparticle surface.

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Section: Stille Coupling Reactionmentioning

confidence: 99%

“…To a solution of the first-generation AB 3 -type dendritic bromide G 1 CH 2 Br (1.96 g, 4 mmol) [35] and 5-bromobenzene- …”

Section: Synthesis Of Ab 3 -Type Dendritic Bromobenzenementioning

confidence: 99%

Air‐Stable and Highly Active Dendritic Phosphine Oxide‐ Stabilized Palladium Nanoparticles: Preparation, Characterization and Applications in the Carbon‐Carbon Bond Formation and Hydrogenation Reactions

Zhang

et al. 2008

Adv Synth Catal

109

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“…More recently others have also employed the fluoride ion to enhance the Stille reaction. [9][10][11]16] On this basis we hypothesized that if the preliminary transmetalation between the organostannane and CuI did exist and it was in equilibrium, then removal of the Bu 3 SnI byproduct as insoluble Bu 3 SnF should favor the formation of the more reactive organocopper species, resulting in enhancement of the reaction (Scheme 1). To our knowledge, the tandem use of CuI and CsF to promote the Stille reaction has not been reported.…”

mentioning

confidence: 99%

Stille Coupling Made Easier—The Synergic Effect of Copper(I) Salts and the Fluoride Ion

2004

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“…Milder bases such as potassium and sodium carbonate did not provide the desired product at all (run 12). [11] Fluoride ion, which was expected to be effective according to the results for organotin cases, [5,12] did not promote the reaction either.…”

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confidence: 99%

Palladium‐Catalyzed Cross‐Coupling Reaction by Means of Organogermanium Trichlorides

et al. 2004

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Phenylation of Alkenyl Triflates: Reaction with Tetrabutylammonium Difluorotriphenylstannate.

Cited by 38 publications

References 0 publications

Air‐Stable and Highly Active Dendritic Phosphine Oxide‐ Stabilized Palladium Nanoparticles: Preparation, Characterization and Applications in the Carbon‐Carbon Bond Formation and Hydrogenation Reactions

Air‐Stable and Highly Active Dendritic Phosphine Oxide‐ Stabilized Palladium Nanoparticles: Preparation, Characterization and Applications in the Carbon‐Carbon Bond Formation and Hydrogenation Reactions

Stille Coupling Made Easier—The Synergic Effect of Copper(I) Salts and the Fluoride Ion

Palladium‐Catalyzed Cross‐Coupling Reaction by Means of Organogermanium Trichlorides

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