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Article: A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling

TitleA supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling
Authors
Issue Date2015
Citation
RSC Advances, 2015, v. 5, n. 5, p. 3590-3596 How to Cite?
Abstract© The Royal Society of Chemistry 2015. A water-soluble, supramolecular catalytic system has been designed based on inclusion complexation between a hydrophobic palladium(ii)-dipyrazole complex bearing an adamantyl (Ad) molecular recognition moiety and a complementary, hydrophilic β-cyclodextrin (β-CD) derivative. The single-crystal molecular structure of the Pd(ii) complex was determined and its host-guest inclusion complexation with heptakis(2,6-di-O-methyl)-β-CD (dmβ-CD) in an aqueous medium was confirmed by 2D NOESY 1H NMR spectroscopy. The catalyst showed high activity for Suzuki-Miyaura coupling of hydrophilic aryl bromides with aryl boronic acids in aqueous organic solvents. In the presence of n-Bu4NBr as a stabilizer, the catalyst-containing reaction solution can be recycled and reused multiple times to catalyze the coupling reaction of fresh substrates once the product has been removed by centrifugation. This work demonstrates a supramolecular complex approach, non-covalently modifying a water insoluble metal complex to provide a water-soluble inclusion system to serve as a recyclable catalyst for potential application in green chemical synthesis. This journal is
Persistent Identifierhttp://hdl.handle.net/10722/219770

 

DC FieldValueLanguage
dc.contributor.authorQi, Miao-
dc.contributor.authorTan, Pei Zi-
dc.contributor.authorXue, Fei-
dc.contributor.authorMalhi, Haripal Singh-
dc.contributor.authorZhang, Zhong Xing-
dc.contributor.authorYoung, David J.-
dc.contributor.authorHor, T. S Andy-
dc.date.accessioned2015-09-23T02:57:55Z-
dc.date.available2015-09-23T02:57:55Z-
dc.date.issued2015-
dc.identifier.citationRSC Advances, 2015, v. 5, n. 5, p. 3590-3596-
dc.identifier.urihttp://hdl.handle.net/10722/219770-
dc.description.abstract© The Royal Society of Chemistry 2015. A water-soluble, supramolecular catalytic system has been designed based on inclusion complexation between a hydrophobic palladium(ii)-dipyrazole complex bearing an adamantyl (Ad) molecular recognition moiety and a complementary, hydrophilic β-cyclodextrin (β-CD) derivative. The single-crystal molecular structure of the Pd(ii) complex was determined and its host-guest inclusion complexation with heptakis(2,6-di-O-methyl)-β-CD (dmβ-CD) in an aqueous medium was confirmed by 2D NOESY 1H NMR spectroscopy. The catalyst showed high activity for Suzuki-Miyaura coupling of hydrophilic aryl bromides with aryl boronic acids in aqueous organic solvents. In the presence of n-Bu4NBr as a stabilizer, the catalyst-containing reaction solution can be recycled and reused multiple times to catalyze the coupling reaction of fresh substrates once the product has been removed by centrifugation. This work demonstrates a supramolecular complex approach, non-covalently modifying a water insoluble metal complex to provide a water-soluble inclusion system to serve as a recyclable catalyst for potential application in green chemical synthesis. This journal is-
dc.languageeng-
dc.relation.ispartofRSC Advances-
dc.titleA supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling-
dc.typeArticle-
dc.description.natureLink_to_subscribed_fulltext-
dc.identifier.doi10.1039/c4ra13953d-
dc.identifier.scopuseid_2-s2.0-84918772920-
dc.identifier.volume5-
dc.identifier.issue5-
dc.identifier.spage3590-
dc.identifier.epage3596-
dc.identifier.eissn2046-2069-

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