Heterogeneous Metal-Organic Framework Catalysts for Suzuki-Miyaura Cross Coupling in the Pharma Industry

Cartagenova, Daniele; Bachmann, Stephan; Bokhoven, Jeroen A. van; Püntener, Kurt; Ranocchiari, Marco

doi:10.2533/chimia.2021.972

Cited by 9 publications

(6 citation statements)

References 60 publications

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“…The choice of the metal in the nodes of the material plays a crucial role: carboxylate‐based MOFs with zirconium nodes are far more stable than those with aluminum and zinc nodes and often retain their structure after being used in catalysis [21b,38,42] . We note, however, that the easier dissolution of MOFs could be advantageous in industrial applications to clean multi‐purpose equipment for the synthesis of drug substances following GMP standards [98] …”

Section: Discussionmentioning

confidence: 99%

“…[21b,38,42] We note, however, that the easier dissolution of MOFs could be advantageous in industrial applications to clean multi-purpose equipment for the synthesis of drug substances following GMP standards. [98] Crystalline compounds, such as COFs and MOFs, are favorable platforms due to their well-defined structure and homogeneous pore size distribution. The possibility of characterizing the materials with crystallographic techniques allows determining the structure of the catalytic active site with atomic resolution.…”

Section: Discussionmentioning

confidence: 99%

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Phosphine‐Functionalized Porous Materials for Catalytic Organic Synthesis

2022

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Dedicated to Professor Cesare Gennari on the occasion of his 70th birthdayPhosphine ligands are of unique importance in catalysis, especially as ligands for transition metals. Homogeneous catalysis is by far the broadest application of phosphines in industrial processes. The heterogenization of phosphines is challenging even though it would appeal to the chemical industry as a valid strategy for recovery and reutilization. In this Review, we discuss approaches for the immobilization of phosphines through the synthesis of phosphine-functionalized porous polymers, such as metal-organic frameworks (MOFs), covalent organic frameworks (COFs), and porous organic polymers (POPs). We critically discuss the synthetic strategies for preparing monomers, linkers, and porous materials. We highlight the most successful applications of phosphine-based porous catalysts and correlate them with their properties, structure, and performance.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Phosphine‐Functionalized Porous Materials for Catalytic Organic Synthesis

2022

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“…In recent years, Ni-containing MOFs have also been proposed as catalysts in various coupling reactions. [18,19] Developments in this area of organic synthesis [20] have mainly been focused on the immobilization of the established ligands from homogeneous catalysis [21,22] onto the surface of a MOF, leading to the development of a sustainable heterogeneous nickel catalyst; [23] and on nickel-decorated covalent organic frameworks for reactions under microwave irradiation, [24] both of which have shown promising results in Suzuki-Miyaura coupling.…”

Section: Introductionmentioning

confidence: 99%

Carbonyl‐Supported Coordination in Imidazolates: A Platform for Designing Porous Nickel‐Based ZIFs as Heterogeneous Catalysts

Škrjanc,

Jankovič,

Meden

et al. 2023

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Zeolitic imidazolate frameworks (ZIFs) are a subclass of metal–organic framework that have attracted considerable attention as potential functional materials due to their high chemical stability and ease of synthesis. ZIFs are usually composed of zinc ions coordinated with imidazole linkers, with some other transition metals, such as Cu(II) and Co(II), also showing potential as ZIF‐forming cations. Despite the importance of nickel in catalysis, no Ni‐based ZIF with permanent porosity is yet reported. It is found that the presence and arrangement of the carbonyl functional groups on the imidazole linker play a crucial role in completing the preferred octahedral coordination of nickel, revealing a promising platform for the rational design of Ni‐based ZIFs for a wide range of catalytic applications. Herein, the synthesis of the first Ni‐based ZIFs is reported and their high potential as heterogeneous catalysts for Suzuki–Miyaura cross‐coupling C─C bond forming reactions is demonstrated.

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“…[1][2][3][4][5][6][7][8][9][10] The development and use of noble metals for the safe, robust and sustainable production of pharmaceutically relevant molecules, through catalytic CÀ C couplings, is a challenge for the academic and industrial chemical communities. [11] Among the various transition metal based catalysts, [12][13][14] Pd-based catalysts exhibit the highest activity in the C-C cross coupling reactions. [15] For instance, the use of Pd-based catalyst in the cross coupling between different types of organoboron derivatives with organic electrophiles (halides, triflates) using a base provides a convenient and straightforward strategy to construct CÀ C bonds.…”

Section: Introductionmentioning

confidence: 99%

“…The formation of C−C bonds using palladium based catalysts (such as in Suzuki or Heck couplings of boronic acids and/or halides) is a ubiquitous reaction in organic synthesis and catalysis for the construction of molecules with industrial and thus societal interest, such as bulk chemicals, fine chemicals and pharmaceuticals [1–10] . The development and use of noble metals for the safe, robust and sustainable production of pharmaceutically relevant molecules, through catalytic C−C couplings, is a challenge for the academic and industrial chemical communities [11] . Among the various transition metal based catalysts, [12–14] Pd‐based catalysts exhibit the highest activity in the C‐C cross coupling reactions [15] .…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Based Metal Organic Frameworks as Heterogeneous Catalysts for C−C Couplings

et al. 2022

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Among the various cross coupling reactions, CÀ C cross coupling reaction has attracted many researchers to investigate in the last four decades. The continuous, constant, and consistent progress in this field fetched a Noble prize in 2010, showing the importance of this reaction in diversified fields. Among the various transition metals studied for this reaction, Pd is one of the metals that has exhibited the highest activity due to its unique features and reactivity. Although Pd-based homogeneous catalyst was the preferred choice for many researchers, the field slowly diverted towards the development of Pd-based heterogeneous catalysts for CÀ C coupling reactions. This is obviously due to the high cost of Pd precursor, its selfdeactivation. In this context, metal organic frameworks (MOFs) are one of the solid catalysts frequently employed as host matrix for the deposition of Pd(II) salts and Pd nanoparticles. This is due to the widespread possibilities available for the functionalization of MOFs and their stability during the synthetic procedure. This review provides the design and development of Pd-based MOFs as heterogeneous catalysts for the CÀ C cross coupling reactions. After a brief introduction on MOFs and the importance of CÀ C coupling reactions, the main part of the review summarizes the catalytic data with respect to Pd(II) and Pd nanoparticles as active sites. The last section provides our views in this field for the further development in the near future. * Readily available reactants * Milder experimental conditions with high yields * Stability of catalysts in water * Reaction may be performed in aqueous and heterogeneous medium * Broad range of functional groups tolerance * High regio-/stereoselectivity * Small quantity of catalysts is sufficient * Applicable in one-pot synthesis * Easy separation boron compound (inorganic) * Environmentally friendly processThe recent advances in heterogeneous catalyst design for surpassing activity, selectivity and specially, stability of their homogeneous counterparts are based in the isolation of the Pd active sites in a solid support by anchoring through different type of bonds. [20][21][22][23][24][25][26][27] In this aspect, one of the solids that has [a] Dr.

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Heterogeneous Metal-Organic Framework Catalysts for Suzuki-Miyaura Cross Coupling in the Pharma Industry

Cited by 9 publications

References 60 publications

Phosphine‐Functionalized Porous Materials for Catalytic Organic Synthesis

Phosphine‐Functionalized Porous Materials for Catalytic Organic Synthesis

Carbonyl‐Supported Coordination in Imidazolates: A Platform for Designing Porous Nickel‐Based ZIFs as Heterogeneous Catalysts

Palladium‐Based Metal Organic Frameworks as Heterogeneous Catalysts for C−C Couplings

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