Metal organic framework-supported N -heterocyclic carbene palladium complex: A highly efficient and reusable heterogeneous catalyst for Suzuki-Miyaura C-C coupling reaction

Bahadori, Mehrnaz; Tangestaninejad, Shahram; Moghadam, Majid; Mirkhani, Valiollah; Mechler, Ádám; Mohammadpoor‐Baltork, Iraj; Zadehahmadi, Farnaz

doi:10.1016/j.micromeso.2017.06.048

Cited by 50 publications

(21 citation statements)

References 49 publications

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“…According to the description of Moghadam and co‐workers, the imidazolium moiety was anchored on MIL‐101(Cr)−NH 2 and consequently Pd–NHC moieties . Both palladium(0) ( 130 b ) and palladium(II) ( 130 a ) species were obtained in this case.…”

Section: Heterogeneous Catalysismentioning

confidence: 88%

Chelating Bis(N‐Heterocyclic Carbene) Palladium‐Catalyzed Reactions

Liu

Gou

Han

2018

Chemistry An Asian Journal

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N-Heterocyclic carbenes (NHCs) have been widely employed in the construction of various metal complexes and applied in the field of catalysis. In this review, a series of palladium complexes comprising chelating bis(NHC) donors (Pd-bis(NHC) complexes) are outlined according to their application in homogeneous catalysis. Examples of metal-organic frameworks containing Pd-bis(NHC) moieties are briefly discussed, in terms of their use in heterogeneous catalysis. The catalytic applications of Pd-bis(NHC) complexes (or moieties in heterogeneous catalysts) are mainly focused on the Mizoroki-Heck, Suzuki-Miyaura, and Sonogashira coupling reactions. Another 14 types of reactions are also summarized beyond these three types of reactions.

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Section: Heterogeneous Catalysismentioning

confidence: 88%

Chelating Bis(N‐Heterocyclic Carbene) Palladium‐Catalyzed Reactions

Liu

Gou

Han

2018

Chemistry An Asian Journal

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“…[93] Chem.E ur.J. In addition to metal catalysts, Cr-MOFs can also be used to anchor homogeneous catalysts such as metal complexes and metalloligands.…”

Section: Chromiummentioning

confidence: 99%

“…Once again, the information availableo nf unctionalized MCM-41 and SBA-15 [203] systemsc an be used to aid these pursuits. [93]) and [CoNi(m 3 -tp) 2 (m 2 -pyz) 2 ]( Ta ble 1, entry 9, ref. Most of the MOFs developedf or coupling reactions are based on or related to knownM OFs such as IRMOF-3, MOF-5, and UiO-66.…”

Section: Future Perspectivesmentioning

confidence: 99%

Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–2018

Kousik

Velmathi

2019

Chemistry A European J

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Metal-organic frameworks (MOFs) are ac lass of crystalline porousm aterials that have been activelyu sed for several industrial and synthetica pplications.M OFs are spatially and geometrically extrapolatedc oordination polymers with intriguing properties such as tunable porosity and dimensionality.Int erms of their catalytic efficiency,MOFs combine the easy recoverability of heterogeneous catalysts with the increased selectivity of biological catalysts. It is therefore not surprising that alot of work on optimizing MOF catalysts for organic transformationsh as been carriedo ut over the past decade. In this review,recent developments in MOF catalysis are summarized, with special attention being paid to CÀC, CÀN, and CÀOc oupling reactions. The influence of pore size, pore environment, and load on catalytic activity is described. Post-synthetics tabilization techniques and hostguest interactions in caged MOF scaffolds are detailed. Mechanistic aspects pertaining to the use of MOFs in asymmetric heterogeneousc atalysis are highlighted and categorized.

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“…Pd@MIL-101-NH 2 (Cr) (0.5), d X = I, DMF:H 2 O (2:1), 60 C, 1 hr 92 [14] 5 Pd/MIX-MOF-NH 2 (0.25), e toluene, 100 C, 3.5 hr 96 [51] 6 P d -HoMOF (0.4), f DMF, 100 C, 2 hr 95 [52] 7…”

Section: Discussionmentioning

confidence: 99%

“…[11,12] Another way is the ligand pre-modification approach in which MOFs can be directly generated by the combination of Pd−NHC-functionalized organic spacers and metal ions. [13][14][15] In this study, MIL-101(Cr) was functionalized with a Pd−NHC moiety using a post-synthetic modification approach (Scheme 1), and was used as an efficient heterogeneous Pd catalyst system in the Suzuki−Miyaura coupling reaction. [16,17] 2 | RESULTS AND DISCUSSION…”

Section: Introductionmentioning

confidence: 99%

Immobilized Pd on a NHC functionalized metal–organic framework MIL‐101(Cr): an efficient heterogeneous catalyst in Suzuki−Miyaura coupling reaction in water

Niknam

Panahi

Khalafi‐Nezhad

2020

Applied Organom Chemis

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A novel Pd−NHC functionalized metal–organic framework (MOF) based on MIL‐101(Cr) was synthesized and used as an efficient heterogeneous catalyst in the C‐C bond formation reactions. Using this heterogeneous Pd catalyst system, the Suzuki−Miyaura coupling reaction was accomplished well in water, and coupling products were obtained in good to excellent yields in short reaction time. The Pd−NHC−MIL‐101(Cr) was characterized using some different techniques, including Fourier transform‐infrared, X‐ray diffraction, scanning electron microscopy, energy‐dispersive X‐ray spectroscopy, transmission electron microscopy (TEM), X‐ray photoelectron spectroscopy, inductively coupled plasma and elemental analysis. The microscopic techniques showed the discrete octahedron structure of MIL‐101(Cr), which is also stable after chemical modification process to prepare the catalyst system. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the structure of the catalyst, while no reducing agent was used. It seems that the NHC groups and imidazolium moieties in the structure of the MOF can reduce Pd (II) to Pd (0) species. This modified MOF substrate can also prevent aggregation of Pd nanoparticles, resulting in high stability of them in organic transformation. The Pd−NHC−MIL‐101(Cr) catalyst system could be simply extracted from the reaction mixture, providing an efficient synthetic method for the synthesis of biaryls derivatives using the aforementioned coupling reaction. The Pd−NHC−MIL‐101(Cr) catalyst could be recycled in this organic reaction with almost consistent catalytic efficiency.

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Metal organic framework-supported N -heterocyclic carbene palladium complex: A highly efficient and reusable heterogeneous catalyst for Suzuki-Miyaura C-C coupling reaction

Cited by 50 publications

References 49 publications

Chelating Bis(N‐Heterocyclic Carbene) Palladium‐Catalyzed Reactions

Chelating Bis(N‐Heterocyclic Carbene) Palladium‐Catalyzed Reactions

Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–2018

Immobilized Pd on a NHC functionalized metal–organic framework MIL‐101(Cr): an efficient heterogeneous catalyst in Suzuki−Miyaura coupling reaction in water

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