Suzuki–Miyaura Cross‐Coupling With Quasi‐Heterogeneous Palladium

Conlon, David A.; Pipik, Brenda; Ferdinand, Simone; LeBlond, Carl; Sowa, John R.; Izzo, Bill; Collins, Paul C.; Ho, Guo‐Jie; Williams, J. M.; Shi, Yao‐Jun; Sun, Yuhang

doi:10.1002/adsc.200303036

Cited by 132 publications

(74 citation statements)

References 36 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: 83%

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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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: 83%

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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“…For instance, Pd leaching under aryl halide action found earlier for the Heck reaction should theoretically (based on scheme 3) occur in the Suzuki reaction. Numerous confirmations of this were, indeed, found, 4,7,10,31,32 moreover the correlation between the activity and the amount of However, from the previous discussion of the Heck chemistry, it can be concluded that distinguishing between true homogeneous catalysis from heterogeneous catalysis in the Suzuki reaction is undoubtedly a very complicated task. Unfortunately, the results of the conventional tests on reaction homogeneity-heterogeneity 33 are ambiguous due to the interconversions of different catalyst forms (Scheme 3).…”

Section: Scheme 2 Heck Reactionmentioning

confidence: 80%

Suzuki reaction: mechanistic multiplicity versus exclusive homogeneous or exclusive heterogeneous catalysis

Kurokhtina¹,

Schmidt²

2009

Arkivoc

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Comparative studies of the kinetics and selectivity of the Suzuki and Heck reactions, the modified tests on homogeneity-heterogeneity and an implementation of the solid-phase variant of the Suzuki reaction indicate a substantial contribution of the heterogeneous mechanism to the Suzuki reaction catalysis which is in contrast to the Heck reaction. The contributions of molecular complexes, colloidal Pd and the larger-sized particles to Suzuki catalysis depend on the nature of the catalyst precursor, the solvent and the temperature of the reaction. It has been established that these contributions change significantly during the reaction as well.

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“…First, experiments showed behavior suggesting heterogeneous catalysis [13]. However, later on, different experimental evidence suggested a homogeneous pathway, as the presence of soluble palladium was observed during the reaction [14]. The problem of the heterogeneous or homogenous nature of the catalytically active species in a classic cross-coupling reaction has also been reviewed [15].…”

Section: Suzuki-miyaura Couplingmentioning

confidence: 99%

Pd/C Catalysis under Microwave Dielectric Heating

2017

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Microwave-assisted organic synthesis (MAOS) provides a novel and efficient means of achieving heat organic reactions. Nevertheless, the potential arcing phenomena via microwave (MW) interaction with solid metal catalysts has limited its use by organic chemists. As arcing phenomena are now better understood, new applications of Pd/C-catalyzed reactions under MW dielectric heating are now possible. In this review, the state of the art, benefits, and challenges of coupling MW heating with heterogeneous Pd/C catalysis are discussed to inform organic chemists about their use with one of the most popular heterogeneous catalysts.

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Suzuki–Miyaura Cross‐Coupling With Quasi‐Heterogeneous Palladium

Abstract: The Suzuki±Miyaura cross-coupling reaction using heterogeneous Pd/C has a homogeneous component. The soluble palladium concentration increases during the reaction reaching a maximum at ca. 90% conversion before falling to < 4 ppm.

Cited by 132 publications

References 36 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

Suzuki reaction: mechanistic multiplicity versus exclusive homogeneous or exclusive heterogeneous catalysis

Pd/C Catalysis under Microwave Dielectric Heating

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