A copper- and solvent-free coupling of acid chlorides with terminal alkynes catalyzed by a polystyrene-supported palladium(0) complex under aerobic conditions

Bakherad, Mohammad; Keivanloo, Ali; Bahramian, Bahram; Rajaie, Mahbobeh

doi:10.1016/j.tetlet.2009.09.029

Cited by 35 publications

(17 citation statements)

References 30 publications

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“…The investigation on recyclability of the diatomite-supported Pd(II) salophen complex showed only a slight decrease of activity (85%) after four reaction cycles. The same group [49] prepared the polystyrene-supported Pd(0) complex depicted in Figure 5. four reaction cycles.…”

Section: Palladium Supported Catalysts For Acyl Sonogashira Reactionsmentioning

confidence: 99%

“…Catalysts 2019, 9, x FOR PEER REVIEW 11 of 35 four reaction cycles. The same group [49] prepared the polystyrene-supported Pd(0) complex depicted in Figure 5. This supported species resulted to be active in the acyl Sonogashira reaction of p-chlorobenzoyl chloride with Ph-C≡CH used as a reference substrate.…”

Section: Palladium Supported Catalysts For Acyl Sonogashira Reactionsmentioning

confidence: 99%

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Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds

Albano

Aronica

2019

Catalysts

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The acyl Sonogashira reaction represents an extension of Sonogashira cross-coupling to acid chlorides which replace aryl or vinyl halides, while terminal acetylenes are used as coupling partners in both reactions. The introduction of a carbonyl functional group on the alkyne backbone determines a radical change in the reactivity of the products. Indeed, α,β-alkynyl ketones can be easily converted into different heterocyclic compounds depending on the experimental conditions employed. Due to its potential, the acyl Sonogashira reaction has been deeply studied with particular attention to the nature of the catalysts and to the structures of both coupling compounds. Considering these two aspects, in this review, a detailed analysis of the literature data regarding the acyl Sonogashira reaction and its role in the synthesis of several heterocyclic derivatives is reported.

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Section: Palladium Supported Catalysts For Acyl Sonogashira Reactionsmentioning

confidence: 99%

Section: Palladium Supported Catalysts For Acyl Sonogashira Reactionsmentioning

confidence: 99%

Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds

Albano

Aronica

2019

Catalysts

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“…Both aromatic and aliphatic alkynes were investigated, while the aryl halide was limited to aromatic iodides. The same catalyst was subsequently used for coupling terminal alkynes with aromatic acid chlorides, using triethylamine as the combined base/solvent ( Scheme 19 ) [ 54 ]. The possibility for recycling the catalyst were also studied and found to be good, with only a small drop in product yield after ten reaction cycles.…”

Section: Palladiummentioning

confidence: 99%

Recent Applications of Polymer Supported Organometallic Catalysts in Organic Synthesis

Kann

2010

Molecules

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Recent developments concerning the application of polymer supported organometallic reagents in solid phase synthesis are reviewed, with a special focus on methodology for carbon-carbon formation. Examples of reactions that are covered include the classical Suzuki, Sonogashira and Heck coupings, but also aryl amination, epoxide opening, rearrangements, metathesis and cyclopropanation. Applications in the field of asymmetric synthesis are also discussed.

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“…The diatom shell, which is composed of amorphous silica, has properties such as high porosity with strong adsorbance ability and excellent thermal resistance. [24 -27] As part of our continuing interest in heterogeneous palladiumcatalyzed Sonogashira coupling reactions, [28,29] we report herein our results demonstrating that the Sonogashira coupling of various aryl halides with terminal acetylenes proceeds in the presence of a diatomite-supported palladium(II) salophen complex under copper-and solvent-free conditions.…”

Section: Introductionmentioning

confidence: 99%

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

Bahramian

Bakherad

Keivanloo

et al. 2011

Applied Organom Chemis

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We report here our observation that, using appropriate reaction conditions, the Sonogashira reaction can be performed without the need for copper catalyst and solvent. Our approach involves the use of diatomite-supported palladium(II) salophen complex as a catalyst and triethylamine as a base. The methodology works, to differing extents, for aryl iodides and bromides. This heterogeneous catalyst can be reused at least five times without any decrease in activity.

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A copper- and solvent-free coupling of acid chlorides with terminal alkynes catalyzed by a polystyrene-supported palladium(0) complex under aerobic conditions

Cited by 35 publications

References 30 publications

Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds

Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds

Recent Applications of Polymer Supported Organometallic Catalysts in Organic Synthesis

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

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