The use of palladium on porous glass for catalytic coupling reactions

Li, Jintong; Mau, Albert W. H.; Strauss, Christopher R.

doi:10.1039/a702457f

Cited by 89 publications

(57 citation statements)

References 28 publications

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“…The authors remark that the TON improves when lowering the catalyst load. [241] This is suggestive of slow leaching of Pd(0) into the solution. [52] Similarly, Pd grafted on mesoporous MCM-41 achieves good TONs (5 Â 10 3 ), but only with activated aryl bromides and acrylates.…”

Section: Scope and Synthetic Applicationsmentioning

confidence: 96%

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

2004

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This review discusses the problems associated with developing high-turnover catalysts for the cross-coupling and Heck reactions. New developments in the area, principally constituted by palladacycles and coordinatively unsaturated Pd catalysts featuring bulky phosphanes of high donicity, are reviewed from a mechanistic and synthetic standpoint, and compared with more traditional catalysts obtained from conventional mono-and polydentate Nand P-based ligands, as well as Pd catalysts without strong ligands, such as Pd colloids or heterogeneous catalysts. Carbene ligands are also briefly presented. Whereas a single, most promising approach to highturnover Pd catalysis cannot presently be defined, it is clear that the new "PdL 1 " catalysts (where L 1 is a monodentate bulky P ligand of high donicity) represent the latest, most important development in Pd research, certainly from the standpoint of scope and probably also from the standpoint of efficiency. High turnovers with these catalysts have been described and their use will certainly increase in the next few years. The review ends with a brief discussion containing practical considerations on how to choose a high TON catalyst for a given Heck or cross-coupling reaction of interest.

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Section: Scope and Synthetic Applicationsmentioning

confidence: 96%

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

2004

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“…An a,b-unsaturated aldehyde was obtained as a major product of a pallado-catalysed coupling reaction of an aryl halide with allyl alcohol either under an air atmosphere or in the presence of CuA C H T U N G T R E N N U N G (OTf) 2 . [23][24][25] But few examples were reported and the selectivity was not complete. Alternatively, direct Heck coupling of aryl halides with acrolein resulted in the formation of these products.…”

Section: Introductionmentioning

confidence: 96%

Efficient Heterogeneously Palladium‐Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydes or 3‐Arylpropionic Esters

et al. 2007

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) 4 ]/NaY} catalyst was applied successfully to the Heck arylation of acrolein diethyl acetal using a large variety of aryl and heteroaryl bromides. Depending on the reaction conditions (Heck versus Cacchi) good to high selectivities toward the 3-arylpropionic esters or to the cinnamaldehydes were achieved, respectively. Under classical Heck conditions, while the catalyst was found to be stable over the two first runs, it showed significant loss of activity from the third cycle. Under Cacchi conditions, the catalyst could not be reused as it led to high dehalogenation rates. All results indicate that the reactions proceed through dissolved palladium species in the bulk solution (leaching). As observed by transmission electronic microscopic (TEM) analyses, while these species can be trapped and stabilised by the zeolite framework under the Heck conditions, they tend to form large palladium(0) aggregates under the Cacchi conditions leading to dehalogenation rather than to the expected Heck coupling.

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“…To complement the reactors, a catalytic membrane of Pd on porous glass tubing was produced [35]. As mentioned in Sect.…”

Section: Applications Of the Mbr And Cmrmentioning

confidence: 99%

“…As mentioned in Sect. 2.6, a catalyst consisting of palladium metal deposited on porous glass tubing was developed for C±C coupling reactions [35]. It was used for reactions conducted continuously or batchwise and could be reused for repeat or different reactions.…”

Section: Metal-catalyzed Processesmentioning

confidence: 99%

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Microwave‐Assisted Organic Chemistry in Pressurized Reactors

Strauss

2002

Microwaves in Organic Synthesis

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The highest priorities for the chemical industry now are process and product safety and the environment [1±5]. New technologies and methods for ªgreenº and sustainable chemistry are subjects of intense activity [6]. In that regard, the potential of microwave heating for organic synthesis attracted interest soon after the first reports [7, 8] appeared in 1986. Early reactions were performed with domestic microwave ovens and relatively primitive containers. Rate enhancement of up to three orders of magnitude was observed, but the time savings were offset by hazards such as deformation of the vessels and explosions.Thus, the major challenge confronting the early microwave chemists was to retain or enhance the benefits of the technology while concurrently avoiding the risks. Several groups concluded that microwave heating was incompatible with organic solvents and investigated solvent-free conditions including ªdryº media, usually with open vessels in domestic microwave ovens [9±12]. That area expanded rapidly, aided by the ready availability of inexpensive microwave equipment and encouraged by a diverse range of reactions awaiting exploration.Synthetic chemists desire well defined reaction conditions. Process chemists demand them. Nonuniform heating and difficulties with mixing and temperature measurement are technical constraints that initially limited the scale of microwave chemistry with ªdryº media and have not yet been overcome. Poor reproducibility also has been reported, probably resulting from differences in performance and operation of individual domestic microwave ovens [13±15]. Consequently, most, if not all, of the disclosed applications of ªdryº media are laboratory-scale preparations. However, as discussed in other chapters, this does not prevent their being interesting and useful.An alternative approach, developed by Bose [16±19] and termed ªmicrowave-induced organic reaction enhancementº (MORE) chemistry, employed polar, high-boiling solvents with open vessels in unmodified domestic microwave ovens. The solvents had dielectric properties suitable for efficient coupling of microwave energy and rapid heating to temperatures that although high, were typically some 20±30 8C 35Microwaves in Organic Synthesis. Edited by Andr Loupy

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The use of palladium on porous glass for catalytic coupling reactions

Abstract: Palladium on porous glass is a useful heterogeneous catalyst for liquid phase organic coupling reactions which can be carried out in the presence of air, without the need for solubilizing and activating ligands.

Cited by 89 publications

References 28 publications

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

Efficient Heterogeneously Palladium‐Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydes or 3‐Arylpropionic Esters

Microwave‐Assisted Organic Chemistry in Pressurized Reactors

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