Control of Pd leaching in Heck reactions of bromoarenes catalyzed by Pd supported on activated carbon

Heidenreich, Roland G.; Krauter, Jürgen G.E.; Pietsch, Jörg; Köhler, Klaus

doi:10.1016/s1381-1169(01)00499-x

Cited by 177 publications

(101 citation statements)

References 32 publications

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“…Therefore, if the reactions were catalyzed heterogeneously, no change in the reaction progress should be expected. This result is consistent with the previous findings that Pd-loaded zeolites and other supported Pd catalysts act as soluble Pd reservoirs for C C coupling reactions [21,[81][82][83][84][85][86][87][88][89][90].…”

Section: Suzuki-miyaura Reactions Of Aryl Chloridessupporting

confidence: 93%

Pd-loaded NaY zeolite as a highly active catalyst for ligandless Suzuki–Miyaura reactions of aryl halides at low Pd loadings under aerobic conditions

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Artok

2007

Journal of Molecular Catalysis A: Chemical

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The Pd(NH 3 ) 4 2+ -loaded NaY zeolite was found to be a highly active catalyst precursor for Suzuki-Miyaura (SM) reactions of aryl bromides and aryl chlorides at low Pd concentrations in air. Aryl bromides and arylboronic acids can couple effectively both in pure water and in N,Ndimethylacetamide/water mixtures (1/1) within minutes with turnover frequencies (TOF) up to 4 × 10 5 h −1 . The presence of a minute amount of water was crucial for the success of the reaction with chloroarenes. The excess amounts of as-received zeolite provided the necessary water for the reaction. The results suggest that the combined use of the water-zeolite system may have a synergistic effect in the reaction.

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Section: Suzuki-miyaura Reactions Of Aryl Chloridessupporting

confidence: 93%

Pd-loaded NaY zeolite as a highly active catalyst for ligandless Suzuki–Miyaura reactions of aryl halides at low Pd loadings under aerobic conditions

Durgun

Aksın

Artok

2007

Journal of Molecular Catalysis A: Chemical

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“…[41,246] The TONs are quite high, up to 3.6 Â 10 4 for the reaction of bromobenzene with styrene, and up to 7.2 Â 10 3 for the analogous reaction of p-methoxybromobenzene. Analogously, Suzuki coupling with phenylboronic acid proceeds with TONs of ca.…”

Section: Scope and Synthetic Applicationsmentioning

confidence: 99%

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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“…This product emerged from a dehalogenation reaction, that can be performed only with metallic catalysts. [9] The [Pd( NH 3 ) 4 ] 2 -NaY catalyst yielded higher conversion of bromobenzene and in NMP double arylated product 2 was observed. Slight leaching of the metal under the reaction conditions cannot be excluded.…”

Section: Influence Of the Solventmentioning

confidence: 94%

Heck Arylation of α,β‐Unsaturated Aldehydes

2003

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Control of Pd leaching in Heck reactions of bromoarenes catalyzed by Pd supported on activated carbon

Cited by 177 publications

References 32 publications

Pd-loaded NaY zeolite as a highly active catalyst for ligandless Suzuki–Miyaura reactions of aryl halides at low Pd loadings under aerobic conditions

Pd-loaded NaY zeolite as a highly active catalyst for ligandless Suzuki–Miyaura reactions of aryl halides at low Pd loadings under aerobic conditions

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

Heck Arylation of α,β‐Unsaturated Aldehydes

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