Selenated NHC-Pd(II) catalyzed Suzuki-Miyaura coupling of ferrocene substituted β-chloro-cinnamaldehydes, acrylonitriles and malononitriles for the synthesis of novel ferrocene derivatives and their solvatochromic studies

Tomar, Vijesh; Upadhyay, Yachana; Srivastava, A. K.; Nemiwal, Meena; Joshi, Rashika; Mathur, Purva

doi:10.1016/j.jorganchem.2021.121752

Cited by 30 publications

(35 citation statements)

References 40 publications

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“…These ligands have been used in the development of homogeneous catalytic systems [18–102] . All such ligands behave as Lewis bases due to the presence of chalcogen (S/Se/Te) donor sites, and form a coordinate (i. e. dative) bond with the metal through such sites.…”

Section: Role Of Ligand Vis‐à‐vis Organochalcogen Ligandsmentioning

confidence: 99%

“…Reactions of these compounds are catalysed by the Pd(II) complex 73 . It is an exceptionally efficient system and also have the ability of catalysing (Scheme 36) the coupling reactions of various arylboronic acids [74] …”

Section: Substrate Scope In Catalysismentioning

confidence: 99%

“…In such reactions, the catalyst is used in very low quantity (0.002 mol%) and the product formation occurs in good yields (72–91 %) within 180 minutes (3 hours). While performing the reactions at 110 °C, K 2 CO 3 is used as a base [74] . However, a reaction with isobutylboronic acid requires very long time (48 hour) to produce reasonable yield (68 %) of the product under the same reaction conditions [74] .…”

Section: Substrate Scope In Catalysismentioning

confidence: 99%

“…In addition to Suzuki coupling, they show catalytic potential for several other chemical transformations [10,11,87–107] too. In the recent past, some of such systems have also been used for its green catalysis in water and room temperature [20,21,27,33,34,44,48,49,50,55,61,63,66,73,74] . Microwave and ultrasound radiations have also been used as non‐conventional sources of energy for its catalysis [18,19,25,30,58,62] …”

Section: Introductionmentioning

confidence: 99%

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Molecular Organosulphur, Organoselenium and Organotellurium Complexes as Homogeneous Transition Metal Catalytic Systems for Suzuki Coupling

et al. 2022

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During last two decades, researchers have employed organochalcogen compounds as ligands for the development of pre‐formed chalcogen ligated molecular complexes. During 2013–2020, various chalcogen containing homogenous catalytic systems for Suzuki Miyaura cross‐coupling reaction have been synthesized. The review provides insights into the synthetic methodologies for the preparation of organochalcogen ligands and their transition metal complexes. Another central aspect discussed is the application of such catalytic systems in Suzuki Miyaura coupling. Rationalization about the effect of temperature, substrate scope, organoborane derivatives and aryl halides employed has been elaborated. Effect of binding mode, ligand framework, chalcogen donor atom, metal and many other aspects that influence the catalytic potential of various systems have also been covered. Various other aspects such as green catalysis, use of non‐conventional energy sources have also been analyzed.

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Section: Role Of Ligand Vis‐à‐vis Organochalcogen Ligandsmentioning

confidence: 99%

Section: Substrate Scope In Catalysismentioning

confidence: 99%

Section: Substrate Scope In Catalysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Molecular Organosulphur, Organoselenium and Organotellurium Complexes as Homogeneous Transition Metal Catalytic Systems for Suzuki Coupling

et al. 2022

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“…The utilization of appropriate supported ligands and the immobilization of ligands on heterogenized metals give a steady and sustainable catalyst framework, resulting in minimal leaching and metal aggregation issues. , Of such ligands, nitrogen-containing ligands and their derivatives have been considerably used as potent ligands, such as Schiff bases, − N-heterocyclic carbenes (NHC), − NNN-pincer ligands, pyrazoles, pyridines, DABCO, N-containing dendrimers, and thiols . Guanidine is a significant class of generally occurring compounds frequently used in natural science and is extensively exploited as catalysts .…”

Section: Introductionmentioning

confidence: 99%

Pd^II on Guanidine-Functionalized Fe₃O₄ Nanoparticles as an Efficient Heterogeneous Catalyst for Suzuki–Miyaura Cross-Coupling and Reduction of Nitroarenes in Aqueous Media

et al. 2021

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This paper presents guanidine-functionalized Fe 3 O 4 magnetic nanoparticle-supported palladium (II) (Fe 3 O 4 @Guanidine-Pd) as an effective catalyst for Suzuki–Miyaura cross-coupling of aryl halides using phenylboronic acids and also for selective reduction of nitroarenes to their corresponding amines. Fe 3 O 4 @Guanidine-Pd synthesized is well characterized using FT-IR spectroscopy, XRD, SEM, TEM, EDX, thermal gravimetric analysis, XPS, inductively coupled plasma-optical emission spectroscopy, and vibrating sample magnetometry analysis. The prepared Fe 3 O 4 @Guanidine-Pd showed effective catalytic performance in the Suzuki–Miyaura coupling reactions by converting aryl halides to their corresponding biaryl derivatives in an aqueous environment in a shorter reaction time and with a meagerly small amount of catalyst (0.22 mol %). Also, the prepared Fe 3 O 4 @Guanidine-Pd effectively reduced nitroarenes to their corresponding amino derivatives in aqueous media at room temperature with a high turnover number and turnover frequency with the least amount of catalyst (0.13 mol %). The most prominent feature of Fe 3 O 4 @Guanidine-Pd as a catalyst is the ease of separation of the catalyst from the reaction mixture after the reaction with the help of an external magnet with good recovery yield and also reuse of the recovered catalyst for a few cycles without significant loss in its catalytic activity.

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An Exploration on Copper‐Based Metal‐Organic Frameworks as Propitious Heterogeneous Catalyst for Coupling Reactions

et al. 2023

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Metal‐organic frameworks (MOFs) have been considered as adaptable alternatives of interest in catalytic reactions. Modern MOFs research and advancements strongly support their employment as catalysts to produce significant organic molecules. Concerning how such substances might be utilized in heterogeneous catalysis, the entire potency of MOFs in value‐added organic transformations must be thoroughly investigated. Standard MOFs components including encapsulation materials, linkers, metal‐nodes, and coated structures frequently provide effective catalytic active sites that provide ways to lessen human efforts to implement novel natural reactions. The significant aspects of using MOFs as recyclable catalysts are their convenient fabrication, consistent porosity, substantial pore volume, reusability and durable framework in addition to cost‐effectiveness. Since MOFs were extensively explored, they may have been used to fabricate medicinal active compounds through coupling and organic transformations. In this review, several Cu‐based MOFs are examined along with their catalytic attributes that assist with the selective fabrication of the product organic moieties via various cross‐coupling reactions.

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Selenated NHC-Pd(II) catalyzed Suzuki-Miyaura coupling of ferrocene substituted β-chloro-cinnamaldehydes, acrylonitriles and malononitriles for the synthesis of novel ferrocene derivatives and their solvatochromic studies

Cited by 30 publications

References 40 publications

Molecular Organosulphur, Organoselenium and Organotellurium Complexes as Homogeneous Transition Metal Catalytic Systems for Suzuki Coupling

Molecular Organosulphur, Organoselenium and Organotellurium Complexes as Homogeneous Transition Metal Catalytic Systems for Suzuki Coupling

Pd^II on Guanidine-Functionalized Fe₃O₄ Nanoparticles as an Efficient Heterogeneous Catalyst for Suzuki–Miyaura Cross-Coupling and Reduction of Nitroarenes in Aqueous Media

An Exploration on Copper‐Based Metal‐Organic Frameworks as Propitious Heterogeneous Catalyst for Coupling Reactions

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Selenated NHC-Pd(II) catalyzed Suzuki-Miyaura coupling of ferrocene substituted β-chloro-cinnamaldehydes, acrylonitriles and malononitriles for the synthesis of novel ferrocene derivatives and their solvatochromic studies

Cited by 30 publications

References 40 publications

Molecular Organosulphur, Organoselenium and Organotellurium Complexes as Homogeneous Transition Metal Catalytic Systems for Suzuki Coupling

Molecular Organosulphur, Organoselenium and Organotellurium Complexes as Homogeneous Transition Metal Catalytic Systems for Suzuki Coupling

PdII on Guanidine-Functionalized Fe3O4 Nanoparticles as an Efficient Heterogeneous Catalyst for Suzuki–Miyaura Cross-Coupling and Reduction of Nitroarenes in Aqueous Media

An Exploration on Copper‐Based Metal‐Organic Frameworks as Propitious Heterogeneous Catalyst for Coupling Reactions

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Pd^II on Guanidine-Functionalized Fe₃O₄ Nanoparticles as an Efficient Heterogeneous Catalyst for Suzuki–Miyaura Cross-Coupling and Reduction of Nitroarenes in Aqueous Media