A Preparatively Convenient Ligand-Free Catalytic PEG 2000 Suzuki−Miyaura Coupling

Razler, Thomas M.; Hsiao, Yi; Qian, Feng; Fu, Ruiling; Khan, R. Kashif M.; Doubleday, Wendel W.

doi:10.1021/jo802277z

Cited by 71 publications

(36 citation statements)

References 31 publications

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“…The eluent was hexanes:ethyl acetate 9:1, which afforded the desired compound as a white solid; yield: 94 mg (38%); mp 136-138 8C (Lit. [35] mp: 138-140 8C). A reaction using the general conditions was carried out with tert-butyl isonitrile (171 mL, 1.5 mmol), aniline (93 mg, 1 mmol), tert-butyldimethyl(pent-4-ynyloxy)silane (198 mg, 1 mmol), and TiA C H T U N G T R E N N U N G (NMe 2 ) 2 A C H T U N G T R E N N U N G (dpma) (1, 32.3 mg, 0.1 mmol) in toluene (2 mL) and was heated for 24 h at 100 8C.…”

Section: -Phenyl-4-butylpyrazole (3n)mentioning

confidence: 99%

Pyrazole Synthesis Using a Titanium‐Catalyzed Multicomponent Coupling Reaction and Synthesis of Withasomnine

et al. 2009

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The titanium-catalyzed 3-component coupling of an alkyne, isonitrile, and amine can be used to generate tautomers of 1,3-diimines. These di-A C H T U N G T R E N N U N G imines produced in situ undergo cyclization with hydrazine and hydrazine derivatives in a one-pot procedure to provide pyrazoles. Seventeen examples of pyrazoles are provided using this one-pot, 4-component procedure from simple starting materials. The regioselectivity of the alkyne addition can be controlled in some cases with catalyst architecture, and regioselectivity of monosubsituted hydrazines to unsymmetrical 1,3-diimines is discussed. This multicomponent coupling strategy was applied to the synthesis of withasomnine in an efficient procedure, which gave the natural product in 24% overall yield from 4-pentyn-1-ol.

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Section: -Phenyl-4-butylpyrazole (3n)mentioning

confidence: 99%

Pyrazole Synthesis Using a Titanium‐Catalyzed Multicomponent Coupling Reaction and Synthesis of Withasomnine

et al. 2009

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“…[1][2][3][4] Usually, carbon-carbon coupling reactions are catalyzed by palladium compound [5][6][7] or Ni-Pd bimetallic catalysts. [8][9][10][11][12][13] On the other hand, the Ni catalysts have many advantages over the Pd catalyst, for example, they are more reactive and often cheaper than the Pd complexes.…”

Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO₂-ZrO₂Composite

Kalbasi¹,

Mosaddegh²

2011

Bulletin of the Korean Chemical Society

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Nickel nanoparticle-poly(N-vinyl-2-pyrrolidone)/TiO 2 -ZrO 2 composite (Ni-PVP/TiO 2 -ZrO 2 ) was prepared by in situ polymerization method. The physical and chemical properties of Ni-PVP/TiO 2 -ZrO 2 were investigated by XRD, FT-IR, BET, TGA, SEM and TEM techniques. The catalytic performance of this novel heterogeneous catalyst was determined for the Suzuki-Miyaura cross-coupling reaction between aryl halides and phenylboronic acid in the presence of methanol-water mixture as solvent. The effects of reaction temperature, the amount of catalyst, amount of support, solvent, and amount of metal for the synthesis of Ni-PVP/TiO 2 -ZrO 2 , were investigated as well as recyclability of the heterogeneous composite. The catalyst used for this synthetically useful transformation showed considerable level of reusability besides very good activity.

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“…[30][31][32][33] and by using them, high yield can mostly be obtained. It has been veried that coordination bonding catalytic active substances with high surface energies and high surface-tovolume ratios can improve supported catalysts' efficiency.…”

mentioning

confidence: 99%

Highly efficient and recyclable water-soluble fullerene-supported PdCl₂ nanocatalyst in Suzuki–Miyaura cross-coupling reaction

Huo

Zheng

et al. 2018

RSC Adv.

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A water-soluble fullerene-supported PdCl 2 nanocatalyst [C 60 -TEG S /PdCl 2 ] was prepared by coordination of water-soluble fullerene nanoparticles with palladium chloride. In pure water, the catalytic activity of nanocatalyst [C 60 -TEG S /PdCl 2 ] for Suzuki-Miyaura cross-coupling reaction was investigated under different reaction conditions. The results showed that biphenyl compounds could be synthesized in high yields at room temperature using 0.01 mol% of [C 60 -TEG S /PdCl 2 ] as the catalyst and K 2 CO 3 as the base with the reaction time of 4 h. The catalyst was recycled five times, and the yield clearly did not decrease.

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A Preparatively Convenient Ligand-Free Catalytic PEG 2000 Suzuki−Miyaura Coupling

Cited by 71 publications

References 31 publications

Pyrazole Synthesis Using a Titanium‐Catalyzed Multicomponent Coupling Reaction and Synthesis of Withasomnine

Pyrazole Synthesis Using a Titanium‐Catalyzed Multicomponent Coupling Reaction and Synthesis of Withasomnine

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO₂-ZrO₂Composite

Highly efficient and recyclable water-soluble fullerene-supported PdCl₂ nanocatalyst in Suzuki–Miyaura cross-coupling reaction

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A Preparatively Convenient Ligand-Free Catalytic PEG 2000 Suzuki−Miyaura Coupling

Cited by 71 publications

References 31 publications

Pyrazole Synthesis Using a Titanium‐Catalyzed Multicomponent Coupling Reaction and Synthesis of Withasomnine

Pyrazole Synthesis Using a Titanium‐Catalyzed Multicomponent Coupling Reaction and Synthesis of Withasomnine

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO2-ZrO2Composite

Highly efficient and recyclable water-soluble fullerene-supported PdCl2 nanocatalyst in Suzuki–Miyaura cross-coupling reaction

Contact Info

Product

Resources

About

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Nickel Nanoparticles Supported on Poly(N-vinyl-2-pyrrolidone)/TiO₂-ZrO₂Composite

Highly efficient and recyclable water-soluble fullerene-supported PdCl₂ nanocatalyst in Suzuki–Miyaura cross-coupling reaction