Preparation of a hybrid organic–inorganic material containing macrocyclic triolefinic 15-membered palladium(0) complexCatalytic activity in Suzuki cross-coupling and butadiene telomerization reactions

Blanco, Belén; Brissart, Marina; Moreno‐Mañas, Marcial; Pleixats, Roser; Mehdi, Ahmad; Reyé, Catherine; Bouquillon, Sandrine; Hénin, Françoise; Мuzart, Jacques

doi:10.1016/j.apcata.2005.07.062

Cited by 37 publications

(4 citation statements)

References 35 publications

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“…In this final section, we highlight a few precatalysts that stand out as warranting further study. For instance, there are a number of recently reported immobilized metal complex catalysts where the nature of the active species is somewhat ambiguous based on the data presented. ,,,,,− These systems represent ideal targets for the approach described here of combining multiple kinetic and poisoning tests to elucidate the location of the truly active species.…”

Section: Intriguing Catalytic Systems Worth Further Studymentioning

confidence: 99%

Mizoroki−Heck Coupling Using Immobilized Molecular Precatalysts: Leaching Active Species from Pd Pincers, Entrapped Pd Salts, and Pd NHC Complexes

2007

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The Mizoroki-Heck reaction is a palladium-catalyzed reaction of both practical importance and scientific significance. Two challenges currently faced by practitioners of the Heck and other palladium-catalyzed coupling reactions are (i) minimizing the costs associated with this reaction by developing high TON catalysts or facilitating catalyst recovery and (ii) elucidating the nature of the active species when using various different precatalysts. These two challenges, one practical and one fundamental, served as our motivation in our studies of immobilized molecular palladium(II) complexes as precatalysts in Mizoroki-Heck reactions. This Forum Article describes our investigations in this area, highlighting our approach to the elucidation of the active catalyst by combining kinetic and poisoning studies of several different related precatalysts, our development of new, selective catalyst poisons, and our quest for stable, recyclable supported Heck, Suzuki, and Sonogashira coupling catalysts. Under high-temperature conditions (120 degrees C), all precatalysts studied are conclusively shown to decompose, liberating soluble, active palladium(0) species that are the true catalysts. Techniques for the elucidation of the nature of the truly active Pd species are enumerated.

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Section: Intriguing Catalytic Systems Worth Further Studymentioning

confidence: 99%

Mizoroki−Heck Coupling Using Immobilized Molecular Precatalysts: Leaching Active Species from Pd Pincers, Entrapped Pd Salts, and Pd NHC Complexes

2007

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“…Another innovative method is to use materials with a priori tuned chemical surfaces and other physical properties (mechanical, optical, etc.). In this trend, photoreactive hybrid organic–inorganic materials are promising candidates. , Besides the advantage of achieving submicrometer resolution, these materials are perfectly modular from the point of view of their bulk or surface properties simply by dealing with their composition . It thus becomes possible to design the material according to the desired use in a tailor-made approach.…”

Section: Discussionmentioning

confidence: 99%

“…92,93 Besides the advantage of achieving submicrometer resolution, these materials are perfectly modular from the point of view of their bulk or surface properties simply by dealing with their composition. 94 It thus becomes possible to design the material according to the desired use in a tailor-made approach. Along with the biological "transformisme" stated by Jean Baptiste Lamarck, who said that function creates the organ, will we witness a chemical " transformisme" in microfluidics?…”

Section: ■ Conclusion and Perspectivesmentioning

confidence: 99%

Microfluidic Systems for Droplet Generation in Aqueous Continuous Phases: A Focus Review

et al. 2019

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Microfluidics is one of the most fascinating fields that researchers have been trying to apply in a large number of scientific disciplines over the past two decades. Among them, the discipline of food and pharmaceutical formulation encountered several obstacles when combining microfluidics with aqueous media. Indeed, the physical properties of liquids at micrometric volumes being particular, the droplet generation within microfluidic devices is a big challenge to be met. This focus review is intended to be an initiation for those who would like to generate microdroplets in microfluidic systems involving aqueous continuous phases. It provides a state-of-the-art look at such systems while focusing on the microfluidic devices used, their applications to form a wide variety of emulsions and particles, and the key role held by the interface between the device channels and the emulsion. This review also leads to reflections on new materials that can be used in microfluidic systems with aqueous continuous phases.

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“…In the last five years, several palladium complexes based on a silica matrix have been developed by sol-gel processes or by anchoring procedures onto mesoporous silica (SBA, MCM type, etc). Oxime [29,30] or imine [31] carbapalladacycle complexes, carbene-bearing palladium complexes , [32] Pd(II) complexes with N-N [33][34][35][36][37][38] or N-X (X = O, S) [39] chelation and triolefinic Pd(0) complex [40,41] have been described and their performances examined in the cross-coupling reactions of aryl iodides or aryl bromides with arylboronic acids. Generally, yields up to 90 % were obtained for the desired coupling product.…”

Section: Introductionmentioning

confidence: 99%

Suzuki–Miyaura Reactions of Aryl Chloride Derivatives with Arylboronic Acids using Mesoporous Silica‐Supported Aryldicyclohexylphosphine

et al. 2007

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The Suzuki-Miyaura reactions using mesoporous-supported aryldicyclohexylphosphine as ligand have been investigated. The catalysts were based on SBA-15 type mesoporous silica which was transformed in a four-step synthesis leading to a phosphine-containing hybrid material The most productive catalytic system studied was generated in situ from this material and the homogeneous palladium complex, PdA C H T U N G T R E N N U N G (OAc) 2 . Other catalytic systems were studied for comparison [homogeneous cataysts, a "preformed" catalyst obtained by reaction of PdCl 2A C H T U N G T R E N N U N G (PhCN) 2 and the phosphine-containing material].Variations involving the solvent system, the substrate aryl chloride and the arylboronic acid reactant were also studied. For both in situ and preformed catalyst systems, high conversions and yields are obtained for activated aryl chlorides. Success of the reaction for unactivated aryl chlorides was limited to the catalyst formed in situ. The catalyst formed in situ was also shown to be reactive under aqueous reaction conditions in the cross-coupling of 1-(4-chlorophenyl)ethanone with phenylboronic acid.

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Preparation of a hybrid organic–inorganic material containing macrocyclic triolefinic 15-membered palladium(0) complexCatalytic activity in Suzuki cross-coupling and butadiene telomerization reactions

Cited by 37 publications

References 35 publications

Mizoroki−Heck Coupling Using Immobilized Molecular Precatalysts: Leaching Active Species from Pd Pincers, Entrapped Pd Salts, and Pd NHC Complexes

Mizoroki−Heck Coupling Using Immobilized Molecular Precatalysts: Leaching Active Species from Pd Pincers, Entrapped Pd Salts, and Pd NHC Complexes

Microfluidic Systems for Droplet Generation in Aqueous Continuous Phases: A Focus Review

Suzuki–Miyaura Reactions of Aryl Chloride Derivatives with Arylboronic Acids using Mesoporous Silica‐Supported Aryldicyclohexylphosphine

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