Palladium on Carbon-Catalyzed Cross-Coupling using Triarylbismuths
Simple and efficient protocols for the 10% palladium on carbon (Pd/C)‐catalyzed cross‐coupling reactions between triarylbismuths and aryl halides have been developed. A variety of iodo‐ and bromobenzenes possessing an electron‐withdrawing group on the aromatic nucleus were smoothly cross‐coupled in...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2012-09, Vol.354 (13), p.2561-2567 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Monguchi, Yasunari Hattori, Tomohiro Miyamoto, Yasuhiro Yanase, Takayoshi Sawama, Yoshinari Sajiki, Hironao |
| description | Simple and efficient protocols for the 10% palladium on carbon (Pd/C)‐catalyzed cross‐coupling reactions between triarylbismuths and aryl halides have been developed. A variety of iodo‐ and bromobenzenes possessing an electron‐withdrawing group on the aromatic nucleus were smoothly cross‐coupled in the presence of 10% Pd/C, sodium phosphate dodecahydrate (Na3PO4⋅12 H2O) and 1,4‐diazabicyclo[2.2.2]octane (DABCO) in heated N‐methyl‐2‐pyrrolidone (NMP) as the solvent. For the arylations of iodobenzenes, the reactions effectively proceeded under the combined use of caesium fluoride (CsF) and 2,2′‐biquinoline. Furthermore, a ligand‐free 10% Pd/C‐catalyzed cross‐coupling reaction between the aryl iodides and triarylbismuths was also established by the addition of tetra‐n‐buthylammonium fluoride trihydrate (TBAF⋅3 H2O) in which the palladium metals were hardly leached from the catalyst into the reaction media. |
| doi_str_mv | 10.1002/adsc.201200179 |
| format | Article |
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A variety of iodo‐ and bromobenzenes possessing an electron‐withdrawing group on the aromatic nucleus were smoothly cross‐coupled in the presence of 10% Pd/C, sodium phosphate dodecahydrate (Na3PO4⋅12 H2O) and 1,4‐diazabicyclo[2.2.2]octane (DABCO) in heated N‐methyl‐2‐pyrrolidone (NMP) as the solvent. For the arylations of iodobenzenes, the reactions effectively proceeded under the combined use of caesium fluoride (CsF) and 2,2′‐biquinoline. Furthermore, a ligand‐free 10% Pd/C‐catalyzed cross‐coupling reaction between the aryl iodides and triarylbismuths was also established by the addition of tetra‐n‐buthylammonium fluoride trihydrate (TBAF⋅3 H2O) in which the palladium metals were hardly leached from the catalyst into the reaction media.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201200179</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aromatic compounds ; bismuth ; Carbon ; Catalysis ; Catalysts: preparations and properties ; Catalytic reactions ; Cesium fluorides ; Chemical reactions ; Chemistry ; Cross coupling ; Exact sciences and technology ; Fluorides ; General and physical chemistry ; Halides ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; heterogeneous catalysis ; Iodides ; ligand-free conditions ; Octane ; Organic chemistry ; Palladium ; Preparations and properties ; Sodium phosphate ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Advanced synthesis & catalysis, 2012-09, Vol.354 (13), p.2561-2567</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><rights>Copyright Wiley Subscription Services, Inc. Sep 2012</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4849-1a5bf73684e78023d52681cf23c71046fbedccac22db75558085de221cb71d683</citedby><cites>FETCH-LOGICAL-c4849-1a5bf73684e78023d52681cf23c71046fbedccac22db75558085de221cb71d683</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.201200179$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201200179$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26341814$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Monguchi, Yasunari</creatorcontrib><creatorcontrib>Hattori, Tomohiro</creatorcontrib><creatorcontrib>Miyamoto, Yasuhiro</creatorcontrib><creatorcontrib>Yanase, Takayoshi</creatorcontrib><creatorcontrib>Sawama, Yoshinari</creatorcontrib><creatorcontrib>Sajiki, Hironao</creatorcontrib><title>Palladium on Carbon-Catalyzed Cross-Coupling using Triarylbismuths</title><title>Advanced synthesis & catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>Simple and efficient protocols for the 10% palladium on carbon (Pd/C)‐catalyzed cross‐coupling reactions between triarylbismuths and aryl halides have been developed. A variety of iodo‐ and bromobenzenes possessing an electron‐withdrawing group on the aromatic nucleus were smoothly cross‐coupled in the presence of 10% Pd/C, sodium phosphate dodecahydrate (Na3PO4⋅12 H2O) and 1,4‐diazabicyclo[2.2.2]octane (DABCO) in heated N‐methyl‐2‐pyrrolidone (NMP) as the solvent. For the arylations of iodobenzenes, the reactions effectively proceeded under the combined use of caesium fluoride (CsF) and 2,2′‐biquinoline. Furthermore, a ligand‐free 10% Pd/C‐catalyzed cross‐coupling reaction between the aryl iodides and triarylbismuths was also established by the addition of tetra‐n‐buthylammonium fluoride trihydrate (TBAF⋅3 H2O) in which the palladium metals were hardly leached from the catalyst into the reaction media.</description><subject>Aromatic compounds</subject><subject>bismuth</subject><subject>Carbon</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Catalytic reactions</subject><subject>Cesium fluorides</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Cross coupling</subject><subject>Exact sciences and technology</subject><subject>Fluorides</subject><subject>General and physical chemistry</subject><subject>Halides</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>heterogeneous catalysis</subject><subject>Iodides</subject><subject>ligand-free conditions</subject><subject>Octane</subject><subject>Organic chemistry</subject><subject>Palladium</subject><subject>Preparations and properties</subject><subject>Sodium phosphate</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkM1Lw0AQxYMo-Hn1XBDBS-rOfudYU20FUaEVj8tms9GtaVJ3E7T-9SZUinjxMjOH33sz86LoFNAQEMKXOg9miBFghEAkO9EBcGAxBZ7sbmeG9qPDEBY9IoU4iK4edVnq3LXLQV0NUu2zuopT3ehy_WXzQerrEOK0blelq14Gbejr3Dvt12XmwrJtXsNxtFfoMtiTn34UPd1cz9NpfPcwuU1Hd7GhkiYxaJYVgnBJrZAIk5xhLsEUmBgBiPIis7kx2mCcZ4IxJpFkucUYTCYg55IcRRcb35Wv31sbGrV0wdju_MrWbVBAE0owSJ506NkfdFG3vuquU5hKRqQEJDpquKFM_6W3hVp5t-xeU4BUH6nqI1XbSDvB-Y-tDkaXhdeVcWGrwpxQkEA7LtlwH660639c1Wg8S3_viDdaFxr7udVq_6a4IIKp5_uJmqPx_XQyA4XINyuBlSo</recordid><startdate>20120917</startdate><enddate>20120917</enddate><creator>Monguchi, Yasunari</creator><creator>Hattori, Tomohiro</creator><creator>Miyamoto, Yasuhiro</creator><creator>Yanase, Takayoshi</creator><creator>Sawama, Yoshinari</creator><creator>Sajiki, Hironao</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20120917</creationdate><title>Palladium on Carbon-Catalyzed Cross-Coupling using Triarylbismuths</title><author>Monguchi, Yasunari ; Hattori, Tomohiro ; Miyamoto, Yasuhiro ; Yanase, Takayoshi ; Sawama, Yoshinari ; Sajiki, Hironao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4849-1a5bf73684e78023d52681cf23c71046fbedccac22db75558085de221cb71d683</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Aromatic compounds</topic><topic>bismuth</topic><topic>Carbon</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Catalytic reactions</topic><topic>Cesium fluorides</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Cross coupling</topic><topic>Exact sciences and technology</topic><topic>Fluorides</topic><topic>General and physical chemistry</topic><topic>Halides</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>heterogeneous catalysis</topic><topic>Iodides</topic><topic>ligand-free conditions</topic><topic>Octane</topic><topic>Organic chemistry</topic><topic>Palladium</topic><topic>Preparations and properties</topic><topic>Sodium phosphate</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Monguchi, Yasunari</creatorcontrib><creatorcontrib>Hattori, Tomohiro</creatorcontrib><creatorcontrib>Miyamoto, Yasuhiro</creatorcontrib><creatorcontrib>Yanase, Takayoshi</creatorcontrib><creatorcontrib>Sawama, Yoshinari</creatorcontrib><creatorcontrib>Sajiki, Hironao</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Monguchi, Yasunari</au><au>Hattori, Tomohiro</au><au>Miyamoto, Yasuhiro</au><au>Yanase, Takayoshi</au><au>Sawama, Yoshinari</au><au>Sajiki, Hironao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium on Carbon-Catalyzed Cross-Coupling using Triarylbismuths</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2012-09-17</date><risdate>2012</risdate><volume>354</volume><issue>13</issue><spage>2561</spage><epage>2567</epage><pages>2561-2567</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Simple and efficient protocols for the 10% palladium on carbon (Pd/C)‐catalyzed cross‐coupling reactions between triarylbismuths and aryl halides have been developed. A variety of iodo‐ and bromobenzenes possessing an electron‐withdrawing group on the aromatic nucleus were smoothly cross‐coupled in the presence of 10% Pd/C, sodium phosphate dodecahydrate (Na3PO4⋅12 H2O) and 1,4‐diazabicyclo[2.2.2]octane (DABCO) in heated N‐methyl‐2‐pyrrolidone (NMP) as the solvent. For the arylations of iodobenzenes, the reactions effectively proceeded under the combined use of caesium fluoride (CsF) and 2,2′‐biquinoline. Furthermore, a ligand‐free 10% Pd/C‐catalyzed cross‐coupling reaction between the aryl iodides and triarylbismuths was also established by the addition of tetra‐n‐buthylammonium fluoride trihydrate (TBAF⋅3 H2O) in which the palladium metals were hardly leached from the catalyst into the reaction media.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201200179</doi><tpages>7</tpages></addata></record> |
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| subjects | Aromatic compounds bismuth Carbon Catalysis Catalysts: preparations and properties Catalytic reactions Cesium fluorides Chemical reactions Chemistry Cross coupling Exact sciences and technology Fluorides General and physical chemistry Halides Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings heterogeneous catalysis Iodides ligand-free conditions Octane Organic chemistry Palladium Preparations and properties Sodium phosphate Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Palladium on Carbon-Catalyzed Cross-Coupling using Triarylbismuths |
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