PLGA-PEG-supported Pd Nanoparticles as Efficient Catalysts for Suzuki-Miyaura Coupling Reactions in Water

Dumas, Anaëlle; Peramo, Arnaud; Desmaële, Didier; Couvreur, Patrick

doi:10.2533/chimia.2016.252

Cited by 10 publications

(12 citation statements)

References 10 publications

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“…On the other hand, cyclic triol phenylborate [34] turned out to give a full conversion in 3 h using 0.005 mol% of catalyst (0.04 mol% of palladium) per mol of substrate ( Table 2, entry 4). Such a superior reactivity of borate salts squared with our previous results with Pd NPs stabilized by PLGA-PEG in water [30]. The hydrolytic stability of the cyclic triol borate derivatives in the reaction conditions (checked by NMR in D2O-PBS) must be emphasized and clearly accounted for the efficiency of the process.…”

Section: Methods Of Formulationsupporting

confidence: 64%

“…Influence of the organoboron derivative on the cross-coupling reaction of N-Boc-4-iodo-Lphenylalanine. Following our early finding that palladium stabilized PLGA-PEG NPs were an efficient catalyst for the Suzuki-Miyaura couplings of 4-iodophenylalanine with phenylboronic acid derivatives, we chose to evaluate the present catalyst in the same model reaction [30]. Thus, reaction of N-Boc-4-iodo-l-phenylalanine (1a) with phenylboronic acid in the presence of 0.005 mol% of Pd-Calix-NS (0.04 mol% of Pd per mol of substrate) in pH 8.0 phosphate buffer at 37 • C reached 40% conversion into diphenylalanine 3a after 3 h ( Table 2, entry 1).…”

Section: Methods Of Formulationmentioning

confidence: 99%

“…), Pd-Calix-NS (0.005 mol%), phosphate buffer (20 mM, pH = 8), 37 °C for 3 h. Conversion determined by 1 H NMR analysis of the C-3 methylene signal. b 0.01% Pd, according to reference [30]. c 1 mol% Pd, according to reference [18].…”

Section: Methods Of Formulationmentioning

confidence: 99%

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A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water

et al. 2020

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Nanoformulated calix[8]arenes functionalized with N-heterocyclic carbene (NHC)-palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 4′-arylated phenylalanines and tyrosines in good yields at low catalyst loading with a wide functional group tolerance.

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Section: Methods Of Formulationsupporting

confidence: 64%

Section: Methods Of Formulationmentioning

confidence: 99%

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A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water

et al. 2020

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“…Recently, Dumas et al proposed the use of Pd-nanoparticles (ca. 5.6 nm diameter) as catalyst for Suzuki-Miyaura reactions in aqueous media for the derivatizations of Boc-protected halophenylalanine as the substrate [95]. In their work, the nanoparticles were stabilized on the surface of larger poly(D,L-lactide-co-glycolide)-block-poly(ethylene glycol) copolymer nanoparticles (PLGA-PEG NPs, ca.…”

Section: Access To and Derivatization Of (Pseudo)halogenated Aromaticmentioning

confidence: 99%

The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

et al. 2017

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Abstract:The (site-selective) derivatization of amino acids and peptides represents an attractive field with potential applications in the establishment of structure-activity relationships and labeling of bioactive compounds. In this respect, bioorthogonal cross-coupling reactions provide valuable means for ready access to peptide analogues with diversified structure and function. Due to the complex and chiral nature of peptides, mild reaction conditions are preferred; hence, a suitable cross-coupling reaction is required for the chemical modification of these challenging substrates. The Suzuki reaction, involving organoboron species, is appropriate given the stability and environmentally benign nature of these reactants and their amenability to be applied in (partial) aqueous reaction conditions, an expected requirement upon the derivatization of peptides. Concerning the halogenated reaction partner, residues bearing halogen moieties can either be introduced directly as halogenated amino acids during solid-phase peptide synthesis (SPPS) or genetically encoded into larger proteins. A reversed approach building in boron in the peptidic backbone is also possible. Furthermore, based on this complementarity, cyclic peptides can be prepared by halogenation, and borylation of two amino acid side chains present within the same peptidic substrate. Here, the Suzuki-Miyaura reaction is a tool to induce the desired cyclization. In this review, we discuss diverse amino acid and peptide-based applications explored by means of this extremely versatile cross-coupling reaction. With the advent of peptide-based drugs, versatile bioorthogonal conversions on these substrates have become highly valuable.

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“…In a 2016 report, Dumas and co-workers described a new nanocatalyst consisting of small palladium nanoparticles stabilized on the surface of poly(d,l-lactide-co-glycolide)block-PEG copolymer nanoparticles (PLGA-PEG NPs) that showed excellent catalytic activity for the modification of biological building blocks via Suzuki-Miyaura cross-coupling reaction in water. 58 Brominated or iodinated amino acids were coupled with arylboronic acids in phosphate buffer in good yields (up to 98% conversion into the coupled amino acid in 2 hours at 37 °C, using the cyclic triolborate as organometallic partner in the presence of only 1 mol% of palladium).…”

Section: Scheme 15 Peg Click-triazolepalladacycle As Precatalyst In Tmentioning

confidence: 99%

The Role of PEG on Pd- and Cu-Catalyzed Cross-Coupling Reactions

et al. 2017

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Carbon–carbon and carbon–heteroatom coupling reactions are among the most important transformations in organic synthesis as they enable complex structures to be formed from readily available compounds under different routes and conditions. Several metal-catalyzed cross-coupling reactions have been developed creating many efficient methods accessible for the direct formation of new bonds between differently hybridized carbon atoms.During the last decade, much effort has been devoted towards improvement of the sustainability of these reactions, such as catalyst recovery and atom efficiency. Polyethylene glycol (PEG) can be used as a medium, as solid-liquid phase transfer catalyst, or even as a polymer support. PEG has been investigated in a wide variety of cross-coupling reactions either as an alternative solvent to the common organic solvents or as a support for catalyst, substrate, and ligand. In this review we will summarize the different roles of PEG in palladium- and copper-catalyzed cross-coupling reactions, with the focus on Heck, Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig, Stille, Fukuyama, and homocoupling reactions. We will highlight the role of PEG, the preparation of PEGylated catalysts and substrates, and the importance for the reaction outcome and applicability.1 Introduction2 PEG in Heck Reactions3 PEG in Homocoupling Reactions4 PEG in Suzuki–Miyaura Reactions5 PEG in Sonogashira Reactions6 PEG in Buchwald–Hartwig Reactions7 PEG in Stille Reactions8 PEG in Fukuyama Reactions9 PEG in Miscellaneous Cross-Coupling Routes10 Conclusions

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PLGA-PEG-supported Pd Nanoparticles as Efficient Catalysts for Suzuki-Miyaura Coupling Reactions in Water

Cited by 10 publications

References 10 publications

A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water

A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water

The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

The Role of PEG on Pd- and Cu-Catalyzed Cross-Coupling Reactions

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