Palladium–tetraphosphine catalysed cross coupling of aryl bromides with arylboronic acids: remarkable influence of the nature of the ligand

Feuerstein, Marie; Laurenti, D.; Bougeant, Céline; Doucet, Henri; Santelli, Maurice

doi:10.1039/b009520f

Cited by 107 publications

(45 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the Suzuki reaction with heretoaryl bromides, for example, it is clear that the maximum TON depends very intimately on the electrophile. [168,169] Thus (Scheme 15), in the bromopyridine series the TON decreases in the order 3-Br > 4-Br > 2-Br, and in the bromothiophene series it decreases in the order 3-Br > 2-Br. A possible interaction between Pd and the heteroatom was invoked, but caution is in order when explaining maximum TONs.…”

Section: ð10þmentioning

confidence: 95%

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

2004

View full text Add to dashboard Cite

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.

show abstract

Section: ð10þmentioning

confidence: 95%

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

2004

View full text Add to dashboard Cite

show abstract

“…Although high TOFs are achievable with conventional dispersed homogeneous and heterogeneous palladium catalyst systems [60][61][62][63], such materials suffer from the drawback of requiring post reaction recovery of the palladium catalyst or higher palladium loadings. The practical viability of the palladium-poly(ionic liquid) catalyst membranes in the present study has been demonstrated for the Suzuki--Miyaura coupling reaction of iodobenzene.…”

Section: Discussionmentioning

confidence: 99%

Palladium–poly(ionic liquid) membranes for permselective sonochemical flow catalysis

Wilson

Kore

Ritchie

et al. 2018

Colloids and Surfaces A: Physicochemical and Engineering Aspect

View full text Add to dashboard Cite

Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-pro t purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. G R A P H I C A L A B S T R A C T A R T I C L E I N F O Keywords:Catalyst membrane Ionic liquid Palladium catalyst Plasmachemical functionalization A B S T R A C TAnisotropic palladium-poly(ionic liquid) catalyst membranes have been prepared by complexation of palladium (II) chloride to poly(ionic liquid) functionalised flexible porous substrates. The practical viability of these low loading (sub 0.1 mol%) palladium catalyst membranes for continuous flow reactions at ambient temperature is demonstrated for the Suzuki-Miyaura carbon-carbon coupling reaction by contacting the reactant mixture with the catalyst membrane and applying sonication. The Suzuki-Miyaura carbon-carbon coupling reaction proceeds at the palladium-poly(ionic liquid) catalyst membrane surface in conjunction with selective permeation (separation) of the desired product species through the underlying porous support. These palladium-poly(ionic liquid) catalyst membranes display minimal metal leaching enabling them to be reused multiple times.

show abstract

“…In some cases, the SM reaction can be performed with as little as 0.000001% catalyst loading. 57,60 4.4. Nickel-catalysed SM cross-coupling reactions As seen from the preceding discussions, several efficient Pd catalyst precursors have been developed that allow aryl iodides, bromides, triflates and chlorides to be effectively cross-coupled with arylboronic acids under mild reaction conditions.…”

Section: Sm Cross-coupling Reactions With Other Novel Palladium Catalmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,646

530

View full text Add to dashboard Cite

Palladium–tetraphosphine catalysed cross coupling of aryl bromides with arylboronic acids: remarkable influence of the nature of the ligand

Cited by 107 publications

References 7 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

Palladium–poly(ionic liquid) membranes for permselective sonochemical flow catalysis

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Contact Info

Product

Resources

About