Activity and Recyclability Improvement Through Adjusting the Tethering Strategy for Pd-Catalyzed Suzuki–Miyaura Coupling Reaction of Aryl Chlorides

Zhang, Jingfan; Wang, Mingda; Guo, Xu; Liu, Shu; Cao, Helin; Li, Yuanlong; Zhou, Quan; Hou, Xiu‐Feng

doi:10.1007/s10562-015-1609-1

Cited by 10 publications

(7 citation statements)

References 63 publications

(65 reference statements)

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“…Originating from the use of (C^C)-chelating biscarbene palladium complexes in the Mizoroki–Heck reaction, we investigated a related series of (C^N)-chelating NHC palladium complexes (Figure ). Several other palladium-containing cations of the latter type comprising the pyrimidyl moiety were reported . We found that, for small substituents at the NHC ligands (e.g., those substituted by a methyl group), two ligands are bound at a cationic palladium center, accompanied by a [Pd(DMSO)Cl 3 ] counterion ( 1 , Figure ).…”

Section: Introductionmentioning

confidence: 60%

Cross-Coupling Catalysis by an Anionic Palladium Complex

2017

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Recent studies have shown that anionic palladium complexes are viable catalysts for a range of catalytic cross-coupling reactions. We present a one-step synthesis of the anionic "ligandless" palladium complex [NBu 4 ][Pd-(DMSO)Cl 3 ] together with its crystal structure. This compound has been shown to be an active precatalyst in the Mizoroki−Heck reaction. Under Jeffery conditions, activated aryl chlorides can be coupled in yields of up to 94% without the need of an additional ligand. The presence of a small amount of water was necessary for product formation. An Amatore−Jutand-type catalytic cycle is consistent with the results presented herein. For comparison with the known mixed complex [(pym-Im-Me) 2 PdCl][Pd(DMSO)Cl 3 ], the cationic complex [(pym-Im-Me) 2 PdCl]PF 6 (pym = pyrimidyl, Im = imidazolin-2-ylidene) has been synthesized and characterized using standard techniques.

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Section: Introductionmentioning

confidence: 60%

Cross-Coupling Catalysis by an Anionic Palladium Complex

2017

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“…The imidazolium salts 92 – 93 were initially prepared by direct quaternization of 2,6-bis(bromomethyl)pyridine with 0.67 equiv of the corresponding N-substituted imidazoles in acetone under reflux for 16–18 h . Addition of 93 to the respective N -alkyl-3-(trialkoxysilyl)propan-1-amine in the presence of a base finally yielded the trialkoxysilyl functionalized NHC precursors 94 – 96 in quantitative yields. , Likewise, pyrrolidine derived trialkoxysilanes were also used with 92 – 93 to synthesize the trialkoxysilyl functionalized NHC precursors 97 – 99 in good yields (70–75%). , Later, the same group employed a similar synthetic strategy to prepare the dioxolane-modified asymmetrical and chiral NHC precursors 102 – 103 , which were then used for the preparation of immobilized chiral Au, Rh, and Pd NHC complexes. , However, in contrast to the syntheses of 97 – 99 , which had long reaction times at room temperature, the alkylation step of the syntheses of 102 – 103 was conducted under microwave irradiation in only 3 h, obtaining the products in quantitative yields. Furthermore, Jia et al .…”

Section: Synthetic Strategies For the Immobilization Of N-heterocycli...mentioning

confidence: 99%

“…As listed in Table , the SBA-15 supported NHC compounds 354 – 368 were obtained by grafting the corresponding NHC compounds 56 , 57 , 76 , 105 , 274 , and 323 – 330 onto SBA-15 type supports (Figure ). ,,,, The SBA-15 supports used in those cases were mainly prepared by literature methods. Some were pretreated with trimethylsilyl chloride before removal of the template reagent, deactivating the silanol groups on the outer surface. ,, Additionally, for most supported compounds decreased surface areas and pore sizes were reported compared to the original SBA-15 supports. ,,,, Furthermore, most of the SBA-15 supported compounds were synthesized by heating or reflux in toluene.…”

Section: Synthetic Strategies For the Immobilization Of N-heterocycli...mentioning

confidence: 99%

“…As indicated above, aryl iodides react more readily in the initial oxidative addition step than bromides and chlorides. Thus, the latter can be considered the more challenging substrates, yet they have been used in Suzuki–Miyaura cross-coupling reactions catalyzed by immobilized Pd–NHC catalysts in several cases (refs , , , , , , , , , , , , , − , , , , , , , , , , ). Silica supported Pd–NHC compounds even allowed coupling reactions of donor-substituted and sterically hindered aryl chlorides in good yields. , A variety of different aryl chlorides bearing electron-donating substituents have also been tested in coupling reactions with phenylboronic acid using norbornene based catalysts .…”

Section: Catalytic Applications Of Immobilized Nhc Compoundsmentioning

confidence: 99%

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Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective

et al. 2017

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Over the course of the past 15 years the success story of N-heterocyclic carbene (NHC) compounds in organic, inorganic, and organometallic chemistry has been extended to another dimension. The immobilization of NHC compounds, undergoing continuous diversification, broadens their range of applications and leads to new solutions for challenges in catalytic and synthetic chemistry. This review intends to present a synthetic toolkit for the immobilization of NHC compounds, giving the reader an overview on synthetic techniques and strategies available in the literature. By individually summarizing and assessing the synthetic steps of the immobilization process, a comprehensive picture of the strategies and methodologies for the immobilization of NHC compounds is presented. Furthermore, the characterization of supported NHC compounds is discussed in detail in order to set up necessary criteria for an in-depth analysis of the immobilized derivatives. Finally, the catalytic applications of immobilized NHC compounds are briefly reviewed to illustrate the practical use of this technique for a broad variety of reaction types.

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“…With this context and our former experience on modification of mesoporous silica materials [34][35][36], we herein report the preparation of a series of highly selective Pb(II) ion-imprinted mesoporous silica materials (Pb-IIMS) for separation of Pb(II).…”

Section: Introductionmentioning

confidence: 99%

Novel Pb(II) ion-imprinted materials based on bis-pyrazolyl functionalized mesoporous silica for the selective removal of Pb(II) in water samples

Cui

Shu

et al. 2017

Microporous and Mesoporous Materials

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Three highly efficient adsorbents Pb-IIMS-SBA-15, Pb-IIMS-MCM-41 and Pb-IIMS-FDU-12 for Pb(II) were prepared by grafting the functional monomer 4-(di (1H-pyrazol-1-yl) methyl) phenol (DPP) on corresponding mesoporous silicas with Pb(II) as temple. All these three Pb(II) ion-imprinted mesoporous silica (Pb-IIMS) were characterized by Fourier transform-infrared spectroscopy (FT-IR), solid-state 29 Si and 13 C NMR spectra, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDX), N 2 adsorption-desorption analysis and small angel X-ray diffraction (XRD). The adsorption experiments revealed three Pb-IIMS all possessed considerable adsorption performance for Pb(II), their adsorption profiles obeyed pseudo-second-order kinetics and Langmuir isotherm model. Compared with their corresponding non-imprinted materials, three Pb-IIMS displayed satisfactory selectivity to Pb(II) over seven competing metal ions. Among them, Pb-IIMS-MCM-41 particularly owned outstanding adsorption performance and selectivity, the maximum adsorption capacity as high as 344.8 mg g-1 , as well as excellent reusability through twelve adsorption-desorption cycles. Additionally,

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Activity and Recyclability Improvement Through Adjusting the Tethering Strategy for Pd-Catalyzed Suzuki–Miyaura Coupling Reaction of Aryl Chlorides

Cited by 10 publications

References 63 publications

Cross-Coupling Catalysis by an Anionic Palladium Complex

Cross-Coupling Catalysis by an Anionic Palladium Complex

Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective

Novel Pb(II) ion-imprinted materials based on bis-pyrazolyl functionalized mesoporous silica for the selective removal of Pb(II) in water samples

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