Synthesis of bridged palladium-PEPPSI complexes and catalytic studies in C–C cross-coupling reactions

İmik, Fatma; Yaşar, Sedat; Özdemır, İsmaıl

doi:10.1016/j.ica.2019.118969

Cited by 28 publications

(11 citation statements)

References 58 publications

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“…Later in 2019 , same group investigated the catalytic activity of phenylene‐bridged bis‐benzimidazolylidene palladium‐PEPPSI complexes in Suzuki‐Miyaura, Heck, and Sonogashira cross‐coupling [66] . The authors found that bimetallic complexes showed better activities than the monometallic analogs and complex 42 a with a 2,3,4,5,6‐pentamethyl benzyl tag exhibited higher catalytic activity due to its extra stability caused by well‐balanced steric and electronic properties.…”

Section: Cross‐coupling Reactionsmentioning

confidence: 99%

“…Later in 2019, same group investigated the catalytic activity of phenylene-bridged bis-benzimidazolylidene palladium-PEP-PSI complexes in Suzuki-Miyaura, Heck, and Sonogashira crosscoupling. [66] The authors found that bimetallic complexes showed better activities than the monometallic analogs and complex 42 a with a 2,3,4,5,6-pentamethyl benzyl tag exhibited higher catalytic activity due to its extra stability caused by wellbalanced steric and electronic properties. Under optimized reaction conditions using 0.5 mol% catalyst, K 2 CO 3 base at rt in i PrOH/H 2 O system, electron-donating and electron-withdrawing aryl bromides and chlorides were coupled with phenylboronic acids to give the products in good yields.…”

Section: Homogeneous Catalystsmentioning

confidence: 99%

“…The possibility of diverse structural modifications with benzimidazole scaffolds makes it a reliable ligand in transition metal catalyzed reactions. In recent years, several multidendate ligands have been developed by anchoring two or three monodentate benzimidazole based NHCs to a pivotal centre-CH 2 [35,38,50,60,67] or a rigid framework for instance, biphenyl, [46] phenylene [66] etc. Moreover, these multidenated benzimidazole NHC ligands were found to show excellent stability towards oxygen as well as moisture, thus acting as potential candidates for cross coupling reactions.…”

Section: Conclusion and Future Outlookmentioning

confidence: 99%

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Recent Advances in Benzimidazole Based NHC‐Metal Complex Catalysed Cross‐Coupling Reactions**

Nair

Jayaraj

2022

ChemistrySelect

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In recent years, there has been a substantial increase in the development of efficient, environmentally compatible and cost‐effective catalysts as a replacement for conventional metal catalysts. Among several catalysts developed, metal‐based N‐Heterocyclic carbene (NHC) catalysts have garnered significant attention due to the unique steric and electronic properties imparted by NHCs, making them suitable for a broad spectrum of chemical transformations. Over a decade, benzimidazole based NHCs have been broadly investigated for the synthesis of metal complexes for a variety of catalytic processes. The interesting properties of benzimidazole scaffolds such as the ease of tailoring its electronic and steric properties via simple synthetic modifications, aids in achieving potential catalysts for cross‐coupling reactions and other hydrofunctional transformations. This review focuses on the synthetic approaches developed over recent years (2015–2021) concerning the structural tuning and modulation of the benzimidazole derived NHC ligands to generate catalytically active metal complexes for cross‐coupling reactions such as Heck, Suzuki, Sonogashira, Kumada and dehydrogenative cross‐coupling reactions.

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Section: Cross‐coupling Reactionsmentioning

confidence: 99%

Section: Homogeneous Catalystsmentioning

confidence: 99%

Section: Conclusion and Future Outlookmentioning

confidence: 99%

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Recent Advances in Benzimidazole Based NHC‐Metal Complex Catalysed Cross‐Coupling Reactions**

Nair

Jayaraj

2022

ChemistrySelect

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“…The optimum reaction conditions for the Suzuki-Miyaura coupling reaction examine in a model reaction with bromoacetophenone and PhB (OH) 2 , and the results are given in Table 1. Our previous studies [71][72][73] showed that the 2-propanol/H 2 O solvent system and K 2 CO 3 base are well compatible at room temperature in the homogeneous catalyze systems. Therefore, to determine the sufficient amount of catalyst directly, different reaction conditions are tested.…”

Section: Catalytic Studiesmentioning

confidence: 99%

Magnetite@MCM‐41 nanoparticles as support material for Pd‐N‐heterocyclic carbene complex: A magnetically separable catalyst for Suzuki–Miyaura reaction

Akkoç

Buğday

Altın

et al. 2021

Applied Organom Chemis

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The Magnetite@MCM‐41@NHC@Pd catalyst was obtained with Pd metal bound to the NHC ligand anchored to the surface of Fe3O4@MCM‐41. It was characterized by Fourier transform infrared (FTIR) spectroscopy, transmission electron microscopy (TEM), X‐ray diffraction (XRD), X‐ray photoelectron spectroscopy (XPS), energy disperse X‐ray analysis (EDX), thermogravimetric analysis (TGA), differential thermal analysis (DTA), and scanning electron microscopy (SEM). The amount of Pd in the Magnetite@MCM‐41@NHC@Pd was measure by inductively coupled plasma–optical emission spectroscopy (ICP‐OES) analysis. The catalytic activity of Magnetite@MCM‐41@NHC@Pd heterogeneous catalyst done on Suzuki–Miyaura reactions of aryl halides with different substituted arylboronic acid derivatives. All coupling reactions afforded excellent yields and up to 408404 Turnover Frequency (TOF) h−1 in the presence of 2 mg of Magnetite@MCM‐41@NHC@Pd catalyst (0.0564 mmol g−1, 0.01127 mmol% Pd) at room temperature in 2‐propanol/H2O (1:2). Moreover, Magnetite@MCM‐41@NHC@Pd catalyst was recover by applying the magnet and reused for another reaction. The catalyst showed excellent structural and chemical stability and reused ten times without a substantial loss in its catalytic performance.

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“…5,6 The combination of carbenes (NHC) and pyridines having a wide range of functionalities enable the fine-tuning of the steric and electronic properties of the catalysts. Some representative examples including the modification of NHC carbene ligands, 7 dimetallic bis-carbene-based, 8 trimetallic tris-carbene-derived, 9 solid phase-supported, 10 benzimidazole-derived amide, 11 bulky arly-substitued, 12 ring-expanded, 13 tetraaryl-functionalized (sterically encumbered) 14 and acenaphtyl-derived 15 species have been reported. Even microwave-assisted flow processes were published using PEPPSI catalysts.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel PEPPSI type Pd–BICAAC Complexes

Nagyházi

Almási

Lukács

et al. 2022

Preprint

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A series of bicyclic alkylamino carbenes (BICAAC) (where N-aryl = dipp, mes, 2,6-dimethyl-4-(dimethylamino)phenyl, 5a-d) and their novel air- and moisture-resistant pyridine (pyridine, 4 dimethylaminopyridine) containing palladium PEPPSI-type Pd(II) complexes (6a-e) were synthetized and characterized. The new palladium complexes have shown high activity in Mizoroki–Heck coupling reaction even at as low as 100 ppm loading (TON up to 10000). Kinetic studies revealed that reactions carried out in the presence of elemental mercury resulted in decrease in activity. It indicates that the coupling reaction may have both molecular and Pd(0)-mediated catalytic paths.

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Synthesis of bridged palladium-PEPPSI complexes and catalytic studies in C–C cross-coupling reactions

Cited by 28 publications

References 58 publications

Recent Advances in Benzimidazole Based NHC‐Metal Complex Catalysed Cross‐Coupling Reactions**

Recent Advances in Benzimidazole Based NHC‐Metal Complex Catalysed Cross‐Coupling Reactions**

Magnetite@MCM‐41 nanoparticles as support material for Pd‐N‐heterocyclic carbene complex: A magnetically separable catalyst for Suzuki–Miyaura reaction

Synthesis and Characterization of Novel PEPPSI type Pd–BICAAC Complexes

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