Transition metals in organic synthesis: Highlights for the year 2003

Söderberg, Björn C.G.

doi:10.1016/j.ccr.2005.03.033

Cited by 13 publications

(5 citation statements)

References 1,691 publications

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“…1−4 On the other hand, transition metals are used as catalysts in a large number of organic reactions, including the carbon–carbon (C–C) coupling reaction using metals like Cu, Cr, Co, Pd, Ni, etc. 5−7 Among these, Pd is special and found to be the metal of the most comprehensive use.…”

Section: Introductionmentioning

confidence: 99%

Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki–Miyaura Coupling Reactions

Chatterjee

Bhattacharya

2018

ACS Omega

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Stable, catalytically active palladium nanoparticles of various average diameters (1.9–7.4 nm) have been synthesized and characterized by X-ray diffraction, spectroscopy, and microscopy techniques to demonstrate remarkable size-dependent and renewed catalytic activity toward the Suzuki–Miyaura coupling reaction in green protocol. The catalytic activity is found to depend on the amount of the reducing agent, stabilizer–precursor ratio, solvent composition, and aryl halides used. The product obtained by this reaction is characterized by 1 H NMR, 13 C NMR, and IR spectroscopy analyses. A newly developed kinetic equation illustrates that while the catalyst particles of the lowest dimension are gradually exposed to the reactants and hence activated due to partial removal of capping polymer from the catalyst surface, others are deactivated due to agglomeration during the progress of the reaction, as conformed by the microscopic profiles of the used and unused catalysts.

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Section: Introductionmentioning

confidence: 99%

Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki–Miyaura Coupling Reactions

Chatterjee

Bhattacharya

2018

ACS Omega

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“…Metal-catalyzed cycloaddition reactions are excellent candidates to include in this reaction category . For instance, a powerful method for the construction of three new bonds in a one-step process is the [2 + 2 + 2] metal-catalyzed cycloaddition of unsaturated moieties (such as three alkynes, two alkynes and an alkene, two alkynes and nitriles, etc.…”

Section: Introductionmentioning

confidence: 99%

“Formal” and Standard Ruthenium-Catalyzed [2 + 2 + 2] Cycloaddition Reaction of 1,6-Diynes to Alkenes: A Mechanistic Density Functional Study

et al. 2008

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"Formal" and standard Ru(II)-catalyzed [2 + 2 + 2] cycloaddition of 1,6-diynes 1 to alkenes gave bicyclic 1,3-cyclohexadienes in relatively good yields. The neutral Ru(II) catalyst was formed in situ by mixing equimolecular amounts of [Cp*Ru(CH3CN)3]PF6 and Et4NCl. Two isomeric bicyclic 1,3-cyclohexadienes 3 and 8 were obtained depending on the cyclic or acyclic nature of the alkene partner. Mechanistic studies on the Ru catalytic cycle revealed a clue for this difference: (a) when acyclic alkenes were used, linear coupling of 1,6-diynes with alkenes was observed giving 1,3,5-trienes 6 as the only initial reaction products, which after a thermal disrotatory 6e-pi electrocyclization led to the final 1,3-cyclohexadienes 3 as probed by NMR studies. This cascade process behaved as a formal Ru-catalyzed [2 + 2 + 2] cycloaddition. (b) With cyclic alkenes, the standard Ru-catalyzed [2 + 2 + 2] cycloaddition occurred, giving the bicyclic 1,3-cyclohexadienes 8 as reaction products. A complete catalytic cycle for the formal and standard Ru-catalyzed [2 + 2 + 2] cycloaddition of acetylene and cyclic and acyclic alkenes with the Cp*RuCl fragment has been proposed and discussed based on DFT/B3LYP calculations. The most likely mechanism for these processes would involve the formation of ruthenacycloheptadiene intermediates XXIII or XXVII depending on the alkene nature. From these complexes, two alternatives could be envisioned: (a) a reductive elimination in the case of cyclic alkenes 7 and (b) a beta-elimination followed by reductive elimination to give 1,3,5-hexatrienes 6 in the case of acyclic alkenes. Final 6e-pi electrocyclization of 6 gave 1,3-cyclohexadienes 3.

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“…The synthesis of 3’-deoxy-3’-fluoro-β-D-ribofuranosyl purine derivatives began with a palladium-catalyzed cross coupling [ 45 – 46 ] to install the aromatic moieties to the 6-position of the purine ring. In order to accomplish efficient cross-couplings of a wide range of aromatic rings, we utilized three different protocols that were employed for Stille and Suzuki reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides

Ren¹,

An²,

Hatala³

et al. 2015

Beilstein J. Org. Chem.

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SummaryA unified synthetic strategy accessing novel 3'-fluorinated purine nucleoside derivatives and their biological evaluation were achieved. Novel 3’-fluorinated analogues were constructed from a common 3’-deoxy-3’-fluororibofuranose intermediate. Employing Suzuki and Stille cross-coupling reactions, fifteen 3’-fluororibose purine nucleosides 1–15 and eight 3’-fluororibose 2-chloro/2-aminopurine nucleosides 16–23 with various substituents at position 6 of the purine ring were efficiently synthesized. Furthermore, 3’-fluorine analogs of natural products nebularine and 6-methylpurine riboside were constructed via our convergent synthetic strategy. Synthesized nucleosides were tested against HT116 (colon cancer) and 143B (osteosarcoma cancer) tumor cell lines. We have demonstrated 3’-fluorine purine nucleoside analogues display potent tumor cell growth inhibition activity at sub- or low micromolar concentration.

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Transition metals in organic synthesis: Highlights for the year 2003

Cited by 13 publications

References 1,691 publications

Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki–Miyaura Coupling Reactions

Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki–Miyaura Coupling Reactions

“Formal” and Standard Ruthenium-Catalyzed [2 + 2 + 2] Cycloaddition Reaction of 1,6-Diynes to Alkenes: A Mechanistic Density Functional Study

Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides

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