In Situ Generation of Highly Active Dissolved Palladium Species from Solid Catalysts—A Concept for the Activation of Aryl Chlorides in the Heck Reaction

Pröckl, Sandra S.; Kleist, Wolfgang; Gruber, Markus; Köhler, Klaus

doi:10.1002/anie.200353473

Cited by 254 publications

(117 citation statements)

References 22 publications

(6 reference statements)

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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%

“…Furthermore, the presence of inherent negative sites may lead to better dispersion of the cationic Pd units by ion exchange. Hence, Pdloaded zeolites were demonstrated to be highly active catalysts for the cross coupling of alkenyl halides with arylboronic acids [19], ␣-arylation of malonate [20], Heck [21], amination [22], Suzuki-Miyaura [23][24][25], and Sonogashira [26] reactions.…”

Section: E-mail Address: Leventartok@iyteedutr (L Artok)mentioning

confidence: 99%

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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: 93%

Section: E-mail Address: Leventartok@iyteedutr (L Artok)mentioning

confidence: 99%

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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“…28,[42][43][44][45][46] In the present study, it could easily be incorrectly assumed from the raw conversion data that 1 and 2 were proficient in all solvent systems. However, it is very apparent from the above hot isolation tests that the predominant catalytic species are different when operated in H 2 O or CH 2 Cl 2 .…”

Section: View Article Onlinementioning

confidence: 78%

Bis(imino)acenaphthene (BIAN)-supported palladium(ii) carbene complexes as effective C–C coupling catalysts and solvent effects in organic and aqueous media

Crawford

Cowley

Humphrey

2014

Catal. Sci. Technol.

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“…[75][76][77][78][79] Among them the zeolites showed exceptional activity and stability. [62,69,70,73] Most of the work reported in this area concerned mainly model reactions, reacting aryl iodides and bromides with styrene or acrylates. Few reports concern the reaction of aryl chlorides with styrene.…”

Section: Introductionmentioning

confidence: 99%

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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In Situ Generation of Highly Active Dissolved Palladium Species from Solid Catalysts—A Concept for the Activation of Aryl Chlorides in the Heck Reaction

Cited by 254 publications

References 22 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

Bis(imino)acenaphthene (BIAN)-supported palladium(ii) carbene complexes as effective C–C coupling catalysts and solvent effects in organic and aqueous media

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

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