One step synthesis of Diflunisal using a Pd-diamine complex

Kylmälä, Tuula; Tois, Jan; Xu, Youjun; Franzén, Robert

doi:10.2478/s11532-009-0068-1

Cited by 7 publications

(3 citation statements)

References 49 publications

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“…32,33 For instance, biaryl segment is the core structure of a number of drugs such as diflunisal (antipyretic non-steroidal antiinflammatory), felbinac (anti-inflammatory) and fenbufen 3 (non-steroidal anti-inflammatory) (Scheme 4). 30,67,68 Several synthetic protocols have been introduced for the construction of functionalized biaryls, 69,70 with most of them relying on the C−C cross-coupling reactions. One of the greatest common processes includes the metalcatalyzed Hiyama and Suzuki coupling reactions.…”

Section: Articlementioning

confidence: 99%

“…28 The biaryl moiety is the core structure of several drugs. [29][30][31] One of the most common processes for the synthesis of biaryls involves the palladium-catalyzed Hiyama and Suzuki-Miyaura coupling reactions of aryl halides with aryl siloxanes and aryl boronic acids, respectively. 32,33 The notable advantages of using aryl boronic acids and organosilane reagents contrast with the drawbacks of Negishi, Stille, and Kumada-Corriu coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

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Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media

2021

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Pd-N-heterocyclic carbene complex immobilized on magnetic nanoparticles is synthesized and characterized by different techniques such as FT-IR, XPS, TEM, EDX, FESEM, VSM, TGA and ICP. The synthesized catalyst was used as a new water dispersible heterogeneous catalyst in the fluoride-free Hiyama, Suzuki and cyanation reactions in pure water. By this method, different types of biaryls and aryl nitriles were synthesized in good to high yields by the reaction of a variety of aryl iodides, bromides and chlorides with triethoxyphenylsilane, phenylboronic acid and K 4 [Fe(CN) 6 ]•3H 2 O, respectively. The presence of sulfonates as hydrophilic groups on the surface of the catalyst offers a highly water dispersible, active and yet magnetically recoverable Pd catalyst. The possibility to perform the reaction in water as a green medium, easy catalyst recovery and reuse by successive extraction and final magnetic separation, and the absence of any additives or co-solvents make this method as an eco-friendly and economical protocol for the synthesis of biaryl derivatives and aryl nitriles.

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Section: Articlementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media

2021

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“…The biaryl motif plays a key role in many pharmaceutical compounds, [140] such as antihypertensive sartans [141] and nonsteroidal antiinflammatory drugs, [142,143] and also in natural products [144] such as cannabinol [145] and many alkaloids. [146][147][148] Selective cross-coupling of aryl-residues is often achieved by using transition metal catalysts.…”

Section: Intrinsic Reaction Coordinatementioning

confidence: 99%

pysisyphus: Exploring potential energy surfaces in ground and excited states

Steinmetzer

Kupfer

Gräfe

2020

Int J of Quantum Chemistry

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Predicting the energetics of chemical transformations requires localizing stationary points on a potential energy surface. While educts and products of a chemical reaction may be known, transition state optimization is challenging as good guesses may be unavailable. Extending stationary point searches to the excited state leads to additional difficulties as several states may be close in energy, requiring efficient state tracking. Here, we report the implementation of pysisyphus, an external optimizer, that allows localization of stationary points not only in the ground state but also for excited state by providing several state-tracking algorithms. pysisyphus offers all necessary tools for calculating reaction paths, starting from the optimization of the reactants, running chain-of-states methods such as the nudged elastic band or the growing string method with subsequent transition state optimization, and a concluding intrinsic reaction coordinate calculation.

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Palladium(II) Complexes with Chelating Biscarbene Ligands in the Catalytic Suzuki–Miyaura Cross‐Coupling Reaction

Micksch

Straßner

2012

Eur J Inorg Chem

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We studied the catalytic activity of palladium(II) complexes with chelating imidazolium and benzimidazolium ligands in the Suzuki–Miyaura cross‐coupling reaction. The methylene‐bridged systems with aryl substituents carrying sterically and electronically different groups (F, NO2, OMe, H, Me, iPr) show good to excellent catalytic activities in the Suzuki–Miyaura cross‐coupling reaction of aryl bromides. The p‐methoxyphenyl‐substituted bis(NHC)–palladium complex was the most active one under our reaction conditions, also in the context of a wide substrate scope. Several ortho‐ as well as para‐substituted aryl bromides were coupled in excellent yields under mild reaction conditions.

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One step synthesis of Diflunisal using a Pd-diamine complex

Cited by 7 publications

References 49 publications

Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media

Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media

pysisyphus: Exploring potential energy surfaces in ground and excited states

Palladium(II) Complexes with Chelating Biscarbene Ligands in the Catalytic Suzuki–Miyaura Cross‐Coupling Reaction

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