The first heterogeneous Sonogashira coupling reaction of aryl halides with terminal alkynes catalyzed by diatomite‐supported palladium(II) salophen complex

Bahramian, Bahram; Bakherad, Mohammad; Keivanloo, Ali; Bakherad, Zohre; Karrabi, Behzad

doi:10.1002/aoc.1778

Cited by 16 publications

(14 citation statements)

References 30 publications

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“…Hex‐1‐yn‐1‐ylbenzene (3ca): 42 mg, 89 % yield. 1 H NMR (400 MHz, CDCl 3 ): δ = 7.40–7.37 (m, 2H), 7.27–7.24 (m, 3H), 2.40 (t, J = 7.2 Hz, 2H), 1.60–1.55 (m, 2H), 1.50–1.44 (m, 2H), 0.94 (t, J = 7.2 Hz, 3H).…”

Section: Methodsmentioning

confidence: 99%

In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor

et al. 2019

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A highly efficient and convenient Negishi cross‐coupling reaction has been developed for the synthesis of unsymmetrical alkynes and enynes in a continuous‐flow process. The reaction proceeds through an in situ generated alkynylzinc reagent by the reaction of lithium acetylide with zinc halide at room temperature followed by a cross‐coupling reaction with aryl or vinyl iodides. The notable features of this work compared to the conventional benchtop method are mild reaction conditions, good to excellent yields, broad functional‐group compatibility, short residence time (73 sec) and especially desilylation of TMS group with the residence time of only 10.5 sec.

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Section: Methodsmentioning

confidence: 99%

In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor

et al. 2019

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“…Palladium-catalysed sp 2 -sp Sonogashira coupling reaction of terminal alkynes with aryl halides is one of the most promising methods for the formation of phenylated alkynes [1]. These products have wide applications in synthesis of natural products, biologically active molecules, heterocycles, molecular electronics, dendrimers and conjugated polymers or nanostructures [2].…”

Section: Introductionmentioning

confidence: 99%

Tetradentate Palladium(II) Salophen Complexes: Synthesis, Characterization and Catalytic Activities in Copper-Free Sonogashira Coupling Reaction

Ahmad

Bahron

Tajuddin

2018

IJET

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This paper reports the synthesis and characterization of three salophen ligands; 2,2'- and 2,2'-((1E,1'E)-(1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(4-methoxylphenol)[L1OME]. The compounds were prepared from condensation reaction between salicylaldehyde, and its derivatives, with orthophenylenediamine. Their palladium(II) complexes, namely PdL1H, PdL1C and PdL1OME were synthesized through insertion reaction between the ligands with palladium(II) acetate. All compounds were characterized through melting point, elemental analysis, i nfrared spectroscopy, 1 H and 13 C NMR spectroscopy. Palladium(II) complexes were tested as homogenous catalysts in copper-free Sonogashira coupling reaction between iodobenzene and phenylacetylene in DMSO using triethylamine as base with 1.0 mmol% catalyst loading. The most performing catalyst was PdL1OME with 91% conversion followed by PdL1H (83%) and PdL1C (27%).

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“…Many palladium catalysts used in the Suzuki-Miyaura and Sonogashira-Hagihara reactions are homogeneous [22][23][24][25] catalysts, in spite of many advantages, are impossible to be recovered and the residual palladium left in the product confines their use in bioactive molecules and large-scale synthesis. In order to overcome these drawbacks, in recent years, great efforts in catalysis research have been devoted to the introduction and application of effective heterogeneous catalysts [26][27][28][29][30][31][32][33]. In this context, ligand-free palladium nanoparticles [34][35][36][37][38][39], as well as different ligands like palladacycles [40][41][42], Nheterocyclic carbene [43], Schiff bases [44][45][46], and dendrimers [47] have been explored to be grafted on various inorganic and organic supports such as mesoporous silica [48][49][50][51][52], ionic liquids [53,54] and polymers [55][56][57][58][59][60][61] for the preparation of heterogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%

Highly active thiol-functionalized SBA-15 supported palladium catalyst for Sonogashira and Suzuki–Miyaura cross-coupling reactions

2015

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ARTICLE This journal isHighly ordered mesoporous silica SBA-15 with pendent 3-mercaptopropyl group has been prepared by condensation of surface silanols and (3-mercaptopropyl)trimethoxysilane. Treatment of the mercaptopropylated SBA-15 with (CH 3 CN) 2 PdCl 2 gave a heterogeneous Pd-catalyst. The immobilized Pd-catalyst served as an efficient heterogeneous catalyst for Sonogashira and Suzuki-Miyaura cross coupling reactions of aryl halides. Furthermore, the SBA-15 supported Pd-catalyst was recovered by a simple filtration from the reaction mixture and reused five times without significant loss of its catalytic activity.

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The first heterogeneous Sonogashira coupling reaction of aryl halides with terminal alkynes catalyzed by diatomite‐supported palladium(II) salophen complex

Cited by 16 publications

References 30 publications

In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor

In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor

Tetradentate Palladium(II) Salophen Complexes: Synthesis, Characterization and Catalytic Activities in Copper-Free Sonogashira Coupling Reaction

Highly active thiol-functionalized SBA-15 supported palladium catalyst for Sonogashira and Suzuki–Miyaura cross-coupling reactions

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