A hydrophilic heterogeneous cobalt catalyst for fluoride-free Hiyama, Suzuki, Heck and Hirao cross-coupling reactions in water

Sobhani, Sara; Moghadam, Hadis Hosseini; Skibsted, Jørgen; Sansano, José M.

doi:10.1039/c9gc03455b

Cited by 42 publications

(46 citation statements)

References 87 publications

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“…[ 15‐16 ] However, the extra additives inevitably increase the system complexity and purification difficulty. The hydrophilic modification on catalysts surface has been widely used to improve the solubility of heterogeneous catalysts in water, including covalent (grafting functional groups and anchoring charged substituents) [ 17‐19 ] and noncovalent (host–guest assembly) approaches. [ 20‐21 ] In this strategy, the hydrophilic environment hinders the adsorption of organic substrates from water, and the anchored attachments may block substrate channels.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Polydopamine‐Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

et al. 2021

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Main observation and conclusion Aqueous heterogeneous catalysis is a green, sustainable catalytic process that attracts increasing attention, but it often suffers from poor mass transfer, substrate adsorption and catalyst dispersion. Herein, we synthesized a type of amphiphilic core‐shell catalysts with a hydrophilic polydopamine (PDA) shell and a hydrophobic dendritic organosilica nanoparticle (DON) core for heterogeneous catalysis in water. The hydrophilic shell allowed the catalyst dispersing well in water, and the hydrophobic core facilitated the absorption of organic reactants. The hierarchical core‐shell structure facilitated rational arrangement of the location of catalytic species to match the reaction sequence. The obtained metal, enzyme and metal‐enzyme amphiphilic catalysts demonstrated improved stability, selectivity and activity in aqueous reactions, including Pd‐catalyzed cross‐couplings (Suzuki, Liebeskind‐Srogl, Heck and Sonogashira), enzymatic enantioselective reduction, chemoenzymatic cascade synthesis of chiral compounds and chemoenzymatic cascade degradation of organophosphates. The amphiphilic catalysts could be easily in situ recovered, and their high catalytic performance was sustained for five cycles.

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Section: Background and Originality Contentmentioning

confidence: 99%

Polydopamine‐Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

et al. 2021

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“…In addition, most of the reported methods suffered from lack of generality for the coupling reactions employing chloroarenes. Continuing with our research on the design and the preparation of novel and attractive catalytic systems to conduct environmentally friendly cross-coupling reactions, 4 herein, we have surveyed the catalytic activity of a novel -Fe2O3@MBD/Pd-Co as the first magnetically recyclable Pd/Co bimetallic catalyst in the Mizoroki-Heck coupling reactions.…”

Section: Mizoroki-heck Cross-coupling Reaction Catalyzed By -Fe2o3@mbd/pd-co In Watermentioning

confidence: 99%

“…Haloarenes are frequently transformed into a variety of valuable compounds catalyzed by transition metals such as palladium, copper, nickel, and cobalt with various ligands through cross-coupling reactions. [1][2][3][4] Concerning the catalytic metals employed, palladium is the most versatile element in industrial and academic research playing the most prominent part in the removal of halogen atom from halogenated organic compounds. Therefore, since the pioneering works, the homogeneous palladium complexes have attracted the interest of scientists to address coupling reactions due to their excellent functional group tolerance, as well as their excellent catalytic efficiency.…”

Section: Introductionmentioning

confidence: 99%

“…As the melamine is rich with nitrogen and contains triazine rings with high stability, melamine-based dendrimers (MBD) with abundant metal-binding nitrogen groups have aroused a lot of interest recently for the incorporation of metal nanoparticles for using in catalytic reactions. [17][18][19] In our continuous interest in developing a greener catalyzed reaction, 4,[20][21][22][23][24][25][26][27][28] herein, a melamine-based dendrimer was built to the 1.5-generation onto the -Fe2O3 surface employing a divergent method to synthesize -Fe2O3@melamine-based dendrimer (-Fe2O3@MBD). Bimetallic Pd-Co alloy nanoparticles were then attached to -Fe2O3@melamine-based dendrimer via a co-complexation method followed by reduction with sodium borohydide.…”

Section: Introductionmentioning

confidence: 99%

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A New Nanomagnetic Pd-Co Bimetallic Alloy as Catalyst in the Mizoroki-Heck and Buchwald–Hartwig Amination Reactions in Aqueous Media

Sobhani

Zarei

Sansano

2021

Preprint

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A Pd-Co bimetallic alloy encapsulated in melamine-based dendrimer supported on magnetic nanoparticles denoted as γ-Fe2O3@MBD/Pd-Co was synthesized by a facile co-complexation-reduction method and characterized sufficiently. The catalytic evaluation of γ-Fe2O3@MBD/Pd-Co showed promising results in the Mizoroki-Heck and Buchwald-Hartwig amination reactions of various iodo-, bromo- and challenging chloroarenes in aqueous media. The synergetic cooperative effect of both Pd and Co and dispersion of the catalyst in water due to the encapsulation of γ-Fe2O3 by melamine-based dendrimer lead to high catalytic performance compared with the monometallic counterparts. The dispersion of the magnetic catalyst also facilitates the recovery and reuse of the catalyst by ten consecutive extraction and final magnetic isolation with no loss of catalytic activity, keeping its structure unaltered. Remarkably, this is the first paper on the use of palladium-cobalt bimetallic catalyst for Buchwald-Hartwig amination reaction and the first magnetically recyclable Pd/Co bimetallic catalyst in the Mizoroki-Heck coupling reactions.

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“… 27 Recently, we have introduced a heterogeneous cobalt catalytic system (mTEG-CS-Co-Schiff-base) for Hiyama, Mizoroki–Heck, Suzuki, and Hirao cross-coupling processes. 28 We have found that this catalyst was unsuccessful for the cyanation reaction of aryl halides. To improve our ongoing work, in this paper, we introduced cobalt nanoparticles immobilized on magnetic chitosan (Fe 3 O 4 @CS-Co) as a new catalyst.…”

Section: Introductionmentioning

confidence: 99%

New Nanomagnetic Heterogeneous Cobalt Catalyst for the Synthesis of Aryl Nitriles and Biaryls

2020

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Cobalt nanoparticles immobilized on magnetic chitosan (Fe 3 O 4 @CS-Co) have been prepared. They were identified using various techniques such as Fourier-transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy, thermogravimetric analysis, vibrating sample magnetometry, X-ray photoelectron spectroscopy, and inductively coupled plasma atomic emission spectroscopy analysis and applied efficiently as a cobalt catalyst in the cyanation and fluoride-/palladium-free Hiyama reactions of different types of aryl halides employing K 4 [Fe(CN) 6 ]·3H 2 O and triethoxyphenylsilane, respectively. After each reaction, the catalyst was isolated and reused for the second run. The catalytic activity of the catalyst was not lost apparently even after five runs. No considerable changes in its chemical structure and morphology were observed. It is worth to note that in this paper, the cobalt catalyst has been used for the first time for the cyanation of aryl halides.

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A hydrophilic heterogeneous cobalt catalyst for fluoride-free Hiyama, Suzuki, Heck and Hirao cross-coupling reactions in water

Abstract: A hydrophilic chitosan-cobalt-Schiff base catalyst denoted as mTEG-CS-Co-Schiff-base was prepared for C–C and C–P cross coupling reactions in water.

Cited by 42 publications

References 87 publications

Polydopamine‐Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

Polydopamine‐Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

A New Nanomagnetic Pd-Co Bimetallic Alloy as Catalyst in the Mizoroki-Heck and Buchwald–Hartwig Amination Reactions in Aqueous Media

New Nanomagnetic Heterogeneous Cobalt Catalyst for the Synthesis of Aryl Nitriles and Biaryls

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