A copper-free Sonogashira reaction using nickel ferrite as catalyst in water

Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Rezvani, Hamid Reza

doi:10.1016/j.catcom.2014.11.018

Cited by 41 publications

(17 citation statements)

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“…20 Nickel ferrite and cobalt ferrite nanoparticles, denoted as NiFe 2 O 4 and CoFe 2 O 4 respectively , are of the most important members of oxide-based spinel ferrites. Herein, in continuation of our previous works, [26][27][28] we wish to report the application of two highly active recyclable spinel catalysts, i.e. 23 Furthermore, it is demonstrated that when the diameter of particle is less than that of a single magnetic domain, spinel ferrite nanoparticles become superparamagnetic, which is very important in macroscopic quantum tunneling between spin states.…”

Section: Introductionmentioning

confidence: 84%

Application of nickel ferrite and cobalt ferrite magnetic nanoparticles in C–O bond formation: a comparative study between their catalytic activities

2015

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Magnetic nanoparticles of nickel ferrite and cobalt ferrite were synthesized and their catalytic activity in the C-O bond formation reaction was compared. Both these spinel systems can catalyze the reaction between various types of aryl halides and phenol derivatives efficiently. The catalysts are easily removed from the reaction medium and can be reused further in several runs. All the reactions resulted in very good to excellent yields under optimized reaction conditions; however, reactions using nickel ferrite as catalyst were completed in relatively shorter reaction times. Also, analyses showed that reusability of the two catalytic systems approximately are comparable. Scheme 2. a) Recovery and reuse of nickel ferrite nanoparticles; and b) Recovery and reuse of cobalt ferrite nanoparticles.Reaction conditions: bromobenzene (1 mmol), phenol (1.1 mol), catalyst (5 mol %), K2CO3 (1.2 mmol), DMF (2 ml) and reaction stirred at 80 °C.

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Section: Introductionmentioning

confidence: 84%

Application of nickel ferrite and cobalt ferrite magnetic nanoparticles in C–O bond formation: a comparative study between their catalytic activities

2015

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“…However, the scope for alkynylation has been limited to α‐haloesters and amides to date. We found two reports, in which α‐alkynylation of a ketone is described, although there is only one reaction example in each report ,. One possible reason why a ketone has not been employed as a substrate would be decomposition or side‐reaction of the starting material and/or product caused by deprotonation of an acidic α‐proton under basic conditions applied in most cross‐coupling reactions.…”

Section: Figurementioning

confidence: 99%

Palladium‐Catalyzed Decarboxylative Alkynylation of α‐Acyloxyketones by C(sp³)−O Bond Cleavage

Doi

Yabuta

Sato

2019

Chemistry A European J

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Palladium‐catalyzed decarboxylative alkynylation of α‐acyloxyketones triggered by C(sp3)−O bond cleavage is disclosed. The decarboxylation strategy featuring a neutral reaction condition enabled an unprecedent catalytic alkynylation of a ketone enolate. The reaction was applied to a variety of substrates, giving desired products in good yields. We successfully obtained X‐ray crystallography of a new palladium–enolate intermediate that was synthesized by a reaction of [Pd(cod)(CH2TMS)2] with XPhos and α‐acyloxyketone at room temperature, indicating facile C(sp3)−O bond disconnection.

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“…We have compared our results with those of the Pd, Ni and Cu based catalysts for the Sonogashira coupling reaction, taking the example of the reaction between iodobenzene and phenylacetylene as shown in Table 3. For example Moghaddam et al and Beletskaya et al prepared diphenylacetylenes in 94 and 93% using nickel based catalyst (Beletskaya et al, 2003;Moghaddam et al, 2015). Stein et al and Zhao et al used the palladium based catalyst for the synthesis of diphenylacetylenes in the range of 82% to 94% (Stein et al, 2015;Zhao and Song, 2015).…”

Section: Catalytic Application Of Cuco 2 S 4 Nanosheetsmentioning

confidence: 99%

Hydrothermally Synthesized CuCo2S4 Nanosheets as an Easily Accessible and Convenient Heterogeneous Catalyst for the Sonogashira Cross-Coupling Reactions

2019

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A high surface area and the possibility of high charge separation and transportability make the two-dimensional (2D) nanomaterials very special in many applications, particularly in the field of catalysis. The usefulness of 2D nanomaterial is positively demonstrated in this study by employing it as an efficient heterogeneous catalyst in Sonogashira cross-coupling reaction, where the later one is well known for the formation of carbon-carbon bonds. 2D nanosheets of CuCo 2 S 4 are synthesized using a hydrothermal synthesis and the average thickness of the sheets is found to be in the range of 10-15 nm. The transparent nanosheets are interconnected to form thick sheets and then aggregated to form a highly open three-dimensional hierarchical structure. This study explores the Sonogashira reaction very efficiently in water/ethanol at room temperature using hydrothermally synthesized CuCo 2 S 4 nanosheets as catalyst for the CC coupling reaction for the first time. The developed method is found to be economic, green, high yields, low catalyst loading and reusability of the catalysts. This present CuCo 2 S 4 nanosheet heterogeneous catalyst afford the Sonogashira coupling of various aryl halides with terminal alkynes, giving a variety of aryl acetylenes in excellent yields and can be recovered by a simple filtration and reused for at least 10 consecutive reactions with almost constant yield and activity.

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A copper-free Sonogashira reaction using nickel ferrite as catalyst in water

Cited by 41 publications

References 36 publications

Application of nickel ferrite and cobalt ferrite magnetic nanoparticles in C–O bond formation: a comparative study between their catalytic activities

Application of nickel ferrite and cobalt ferrite magnetic nanoparticles in C–O bond formation: a comparative study between their catalytic activities

Palladium‐Catalyzed Decarboxylative Alkynylation of α‐Acyloxyketones by C(sp³)−O Bond Cleavage

Hydrothermally Synthesized CuCo2S4 Nanosheets as an Easily Accessible and Convenient Heterogeneous Catalyst for the Sonogashira Cross-Coupling Reactions

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A copper-free Sonogashira reaction using nickel ferrite as catalyst in water

Cited by 41 publications

References 36 publications

Application of nickel ferrite and cobalt ferrite magnetic nanoparticles in C–O bond formation: a comparative study between their catalytic activities

Application of nickel ferrite and cobalt ferrite magnetic nanoparticles in C–O bond formation: a comparative study between their catalytic activities

Palladium‐Catalyzed Decarboxylative Alkynylation of α‐Acyloxyketones by C(sp3)−O Bond Cleavage

Hydrothermally Synthesized CuCo2S4 Nanosheets as an Easily Accessible and Convenient Heterogeneous Catalyst for the Sonogashira Cross-Coupling Reactions

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Palladium‐Catalyzed Decarboxylative Alkynylation of α‐Acyloxyketones by C(sp³)−O Bond Cleavage