Highly selective Suzuki reaction catalysed by a molecular Pd–P-MOF catalyst under mild conditions: role of ligands and palladium speciation

Cartagenova, Daniele; Bachmann, Stephan; Püntener, Kurt; Scalone, Michelangelo; Newton, Mark A.; Esteves, Fabio A. Peixoto; Rohrbach, Thomas; Zimmermann, Patrik P.; Bokhoven, Jeroen van; Ranocchiari, Marco

doi:10.1039/d1cy01351c

Cited by 19 publications

(12 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The hydrolysis of the methyl ester moieties with lithium hydroxide yielded 3 (Scheme 3). [40] Extended versions of 3 were targeted to build isoreticular networks with larger pore sizes. The synthetic route to 2-(diphenylphosphineyl)-[1,1'-biphenyl]-4,4'-dicarboxylic acid (4) started with the bromination of 4-iodobenzoic acid by Nbromosuccinimide (NBS).…”

Section: Synthesis Of P-mof Linkersmentioning

confidence: 99%

“…The textural properties are measured with X‐ray diffraction (XRD) experiments, either on single crystals (SCXRD) or on powder samples (PXRD), to determine their crystalline structure and gas sorption experiments to study their porosity. The chemical speciation is studied by element‐specific techniques, such as nuclear magnetic resonance (NMR) spectroscopy, [21b,39,45,59] X‐ray absorption spectroscopy (XAS) [38,40,42,60] and X‐ray photoelectron spectroscopy (XPS) [36,57,61] …”

Section: Synthesis Of Phosphine‐functionalized Porous Materials and C...mentioning

confidence: 99%

See 1 more Smart Citation

Phosphine‐Functionalized Porous Materials for Catalytic Organic Synthesis

2022

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Synthesis Of P-mof Linkersmentioning

confidence: 99%

Section: Synthesis Of Phosphine‐functionalized Porous Materials and C...mentioning

confidence: 99%

Phosphine‐Functionalized Porous Materials for Catalytic Organic Synthesis

2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…In another example, phosphine groups at the organic linker was modified by grafting Pd sites to obtain Pd-P-modified MIL-101 MOF. [89] The catalyst (3 mol% Pd) was employed in the Suzuki-Miyaura coupling between 3-bromoanisole and phenylboronic acid at 90 °C using 3 eq. of TEA.…”

Section: Pd At N-heterocyclic Carbenesmentioning

confidence: 99%

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

et al. 2022

View full text Add to dashboard Cite

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.

show abstract

“…Also, these nanoparticles, which have a core/shell structure, can be used to create magnetic nanocatalysts that have many applications in the field of medicine, such as purification of enzymes, absorption and release of pharmaceutical biomolecules, and targeted drug delivery. [2][3][4][5][6] In order to increase the efficiency of magnetic nanocatalysts, their heterogeneous surface should be insulated first with a coating such as silica in order to avoid excessive oxidation of the surface by the environment and prevent it from becoming lumpy (that is, damage to the core/shell structure). Also, the presence of this silicate coating increases the efficiency of its surface in performing various chemical and biochemical reactions and also provides it with a biocompatibility property that has antibacterial effects.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%