Chemically modified cyclodextrins adsorbed on Pd/C particles: New opportunities to generate highly chemo- and stereoselective catalysts for Heck reaction

Cassez, Andy; Kania, Nicolas; Hapiot, F.; Fourmentin, Sophie; Monflier, Éric; Ponchel, A.

doi:10.1016/j.catcom.2007.11.031

Cited by 45 publications

(31 citation statements)

References 29 publications

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“…Especially, they have outstanding catalyst activity in many organic reactions such as deoxygenation of fatty acids [8], Heck reaction [9], formic acid electro-oxidation [10], and selective oxidation of organic compounds [11]. In most reactions, the catalysts are homogeneous nanoparticles complexed by ligands including carbene, phosphine, amine, and dibenzylidene acetone.…”

Section: Introductionmentioning

confidence: 99%

Preparation and catalytic properties of composites with palladium nanoparticles and poly(methacrylic acid) microspheres

Chen

et al. 2014

Polymer Composites

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Palladium (Pd) nanoparticles with different sizes are in situ synthesized by reduction of PdCl2 with NaBH4 as reductant in the presence of poly(methacrylic acid) (PMAA)microspheres. The obtained PMAA/Pd composites are characterized by Fourier transform infrared spectra, X‐ray diffraction, and Transmission electron microscopy. The catalytic activity of the PMAA/Pd composites is investigated using a model reaction, that is, reduction of p‐nitrophenol to p‐aminophenol. The reaction shows first‐order kinetics, and the reaction rate increases with increasing reaction temperature, p‐nitrophenol concentration, and loadings of Pd nanoparticles on PMAA microspheres. The PMAA/Pd composites exhibit good stability, ascribing to the Pd nanoparticles stabilized by PMAA microspheres. POLYM. COMPOS., 35:2251–2260, 2014. © 2014 Society of Plastics Engineers

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Section: Introductionmentioning

confidence: 99%

Preparation and catalytic properties of composites with palladium nanoparticles and poly(methacrylic acid) microspheres

Chen

et al. 2014

Polymer Composites

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“…For comparison, in a closely related study by Cassez et al, [12] the increase in activity of Heck reactions catalyzed by Pd/C/randomly methylated b-CD was proposed to be related to the adsorption of cyclodextrin on the catalytic surface, in which the reaction takes place. Nevertheless, this idea contrasts with that prevailing here.…”

Section: Resultsmentioning

confidence: 96%

“…This behavior has already been observed by Cassez and co-workers in a different CD system. [12] Acrylonitrile was quite unreactive at this H 2 O:DMF ratio, yielding cinnamonitriles only upon using a higher DMF ratio (1:2). In general, the presence of a-HPCD led to the desired cross-coupling derivative with an effective chemoselectivity ( Table 2, entries 1 and 5) whereas biphenyl (Ullmann coupling) was the only product detected in its absence ( Table 2, entries 2 and 6).…”

Section: Resultsmentioning

confidence: 98%

Palladium on Calcium Carbonate Combined to 2‐Hydroxypropyl‐α/β‐cyclodextrins: A Selective Catalytic System for Aqueous Heck Coupling and Hydroarylation

et al. 2008

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An efficient, selective and recoverable catalytic system for ligand-free aqueous Heck reactions using hydroxypropylated cyclodextrins (HPCDs) and palladium on calcium carbonate (Pd/CaCO 3 ) is highlighted. Remarkably, stereo-and chemoselectivities could be tuned by the cavity size of cyclodextrins, exploiting the relevance of host-guest interactions. UVVis experiments have led to strong evidence concerning an interplay between Pd(II) and a-HPCD, possibly ascribed to a reduction/stabilization effect of CDs. Unexpectedly, hydroarylation was the favored pathway with acrylonitrile which provided access to 3-phenylpropionitrile derivatives without usual hydride donors. Finally, determination of soluble PdA C H T U N G T R E N N U N G (0/II) via AAS enabled the definition of a predominant homogeneous mechanism in which TONs over 5000 were observed.

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“…Cassez et al [17] suggested that application of cyclodextrins in the palladium-charcoal-catalyzed Heck reaction leads to multiple advantages. They have demonstrated that the use of randomly-methylated beta-cyclodextrin (RaMe-β-CD) affects the catalytic sites of Pd/C contributing greatly to the increase of the reaction's chemo-and stereo-selectivity.…”

Section: Methodsmentioning

confidence: 99%

Cyclodextrins in Asymmetric and Stereospecific Synthesis

Macaev

Boldescu

2015

Symmetry

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Abstract:Since their discovery, cyclodextrins have widely been used as green and easily available alternatives to promoters or catalysts of different chemical reactions in water. This review covers the research and application of cyclodextrins and their derivatives in asymmetric and stereospecific syntheses, with their division into three main groups: (1) cyclodextrins promoting asymmetric and stereospecific catalysis in water; (2) cyclodextrins' complexes with transition metals as asymmetric and stereospecific catalysts; and (3) cyclodextrins' non-metallic derivatives as asymmetric and stereospecific catalysts. The scope of this review is to systematize existing information on the contribution of cyclodextrins to asymmetric and stereospecific synthesis and, thus, to facilitate further development in this direction.

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Chemically modified cyclodextrins adsorbed on Pd/C particles: New opportunities to generate highly chemo- and stereoselective catalysts for Heck reaction

Cited by 45 publications

References 29 publications

Preparation and catalytic properties of composites with palladium nanoparticles and poly(methacrylic acid) microspheres

Preparation and catalytic properties of composites with palladium nanoparticles and poly(methacrylic acid) microspheres

Palladium on Calcium Carbonate Combined to 2‐Hydroxypropyl‐α/β‐cyclodextrins: A Selective Catalytic System for Aqueous Heck Coupling and Hydroarylation

Cyclodextrins in Asymmetric and Stereospecific Synthesis

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