Synthesis and Characterization of a Cationic Phthalimido-Functionalized N-Heterocyclic Carbene Complex of Palladium(II) and Its Catalytic Activity
A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been synthesized from [3‐methyl‐1‐(2′‐phthalimidoethyl)imidazolium] hexafluorophosphate ([NHCMe,PhtH]PF6) by transmetalation and isolated in 67 % yield. The title complex has been applied as catalyst in the...
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| Veröffentlicht in: | European journal of inorganic chemistry 2014-03, Vol.2014 (7), p.1225-1230 |
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| container_title | European journal of inorganic chemistry |
| container_volume | 2014 |
| creator | Goh, Serena L. M. Högerl, Manuel P. Jokić, Nadežda B. Tanase, Alexandrina D. Bechlars, Bettina Baratta, Walter Mink, János Kühn, Fritz E. |
| description | A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been synthesized from [3‐methyl‐1‐(2′‐phthalimidoethyl)imidazolium] hexafluorophosphate ([NHCMe,PhtH]PF6) by transmetalation and isolated in 67 % yield. The title complex has been applied as catalyst in the Suzuki–Miyaura cross‐coupling reaction under benign aqueous conditions. The catalyst is active without any observable initiation period. High average turnover frequencies (TOFs) of up to 55000 h–1 have been reached with catalyst concentrations as low as 0.01 mol‐%.
A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been prepared in high yield. The complex was activated instantly, without an initiation period, in the Suzuki–Miyaura cross‐coupling reaction under benign aqueous aerobic conditions. Turnover frequencies (TOFs) up to 55000 h–1, were achieved with 0.01 mol‐% of the complex. |
| doi_str_mv | 10.1002/ejic.201301277 |
| format | Article |
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A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been prepared in high yield. The complex was activated instantly, without an initiation period, in the Suzuki–Miyaura cross‐coupling reaction under benign aqueous aerobic conditions. Turnover frequencies (TOFs) up to 55000 h–1, were achieved with 0.01 mol‐% of the complex.</description><identifier>ISSN: 1434-1948</identifier><identifier>EISSN: 1099-0682</identifier><identifier>DOI: 10.1002/ejic.201301277</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activated ; Carbenes ; Catalysts ; Catalytic activity ; Cationic ; Cross-coupling ; Homogeneous catalysis ; N ligands ; Palladium ; Synthesis</subject><ispartof>European journal of inorganic chemistry, 2014-03, Vol.2014 (7), p.1225-1230</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3887-6f5d1b79987fb7a5b0f133e8fcc99421c01ef6f9044200f951b1135bf41d03013</citedby><cites>FETCH-LOGICAL-c3887-6f5d1b79987fb7a5b0f133e8fcc99421c01ef6f9044200f951b1135bf41d03013</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%2Fejic.201301277$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejic.201301277$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids></links><search><creatorcontrib>Goh, Serena L. M.</creatorcontrib><creatorcontrib>Högerl, Manuel P.</creatorcontrib><creatorcontrib>Jokić, Nadežda B.</creatorcontrib><creatorcontrib>Tanase, Alexandrina D.</creatorcontrib><creatorcontrib>Bechlars, Bettina</creatorcontrib><creatorcontrib>Baratta, Walter</creatorcontrib><creatorcontrib>Mink, János</creatorcontrib><creatorcontrib>Kühn, Fritz E.</creatorcontrib><title>Synthesis and Characterization of a Cationic Phthalimido-Functionalized N-Heterocyclic Carbene Complex of Palladium(II) and Its Catalytic Activity</title><title>European journal of inorganic chemistry</title><addtitle>Eur. J. Inorg. Chem</addtitle><description>A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been synthesized from [3‐methyl‐1‐(2′‐phthalimidoethyl)imidazolium] hexafluorophosphate ([NHCMe,PhtH]PF6) by transmetalation and isolated in 67 % yield. The title complex has been applied as catalyst in the Suzuki–Miyaura cross‐coupling reaction under benign aqueous conditions. The catalyst is active without any observable initiation period. High average turnover frequencies (TOFs) of up to 55000 h–1 have been reached with catalyst concentrations as low as 0.01 mol‐%.
A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been prepared in high yield. The complex was activated instantly, without an initiation period, in the Suzuki–Miyaura cross‐coupling reaction under benign aqueous aerobic conditions. Turnover frequencies (TOFs) up to 55000 h–1, were achieved with 0.01 mol‐% of the complex.</description><subject>Activated</subject><subject>Carbenes</subject><subject>Catalysts</subject><subject>Catalytic activity</subject><subject>Cationic</subject><subject>Cross-coupling</subject><subject>Homogeneous catalysis</subject><subject>N ligands</subject><subject>Palladium</subject><subject>Synthesis</subject><issn>1434-1948</issn><issn>1099-0682</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkU1v1DAQhiMEEqVw5RyJSzlkmYmTOD5WUdtNtS2V-JK4WI5ja73kY2s70PRn9BfjdFGFuHDy2HqedzyaKHqLsEKA9IPaGblKAQlgSumz6AiBsQSKMn0e6oxkCbKsfBm9cm4HAARIcRQ9fJoHv1XOuFgMbVxthRXSK2vuhTfjEI86FnH1WBsZ32z9VnSmN-2YnE-DXJ7D_V618XWyVsEb5Sy7QFbCNmpQcTX2-07dLTk3outEa6b-pK7fP3arvVuyRTf7oJyGuJ_Gz6-jF1p0Tr35cx5HX87PPlfrZPPxoq5ON4kkZUmTQuctNpSxkuqGirwBjYSoUkvJWJaiBFS60AyyLAXQLMcGkeSNzrANwyM5jk4OuXs73k7Ked4bJ1X45KDGyXEsKBZACeQBffcPuhsnG0YPVJ4VAEhzCNTqQEk7OmeV5ntremFnjsCXFfFlRfxpRUFgB-GX6dT8H5qfXdbV325ycI3z6u7JFfYHLyihOf92fcHT9dX6K736zjfkN8sPpPc</recordid><startdate>201403</startdate><enddate>201403</enddate><creator>Goh, Serena L. 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M. ; Högerl, Manuel P. ; Jokić, Nadežda B. ; Tanase, Alexandrina D. ; Bechlars, Bettina ; Baratta, Walter ; Mink, János ; Kühn, Fritz E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3887-6f5d1b79987fb7a5b0f133e8fcc99421c01ef6f9044200f951b1135bf41d03013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Activated</topic><topic>Carbenes</topic><topic>Catalysts</topic><topic>Catalytic activity</topic><topic>Cationic</topic><topic>Cross-coupling</topic><topic>Homogeneous catalysis</topic><topic>N ligands</topic><topic>Palladium</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goh, Serena L. M.</creatorcontrib><creatorcontrib>Högerl, Manuel P.</creatorcontrib><creatorcontrib>Jokić, Nadežda B.</creatorcontrib><creatorcontrib>Tanase, Alexandrina D.</creatorcontrib><creatorcontrib>Bechlars, Bettina</creatorcontrib><creatorcontrib>Baratta, Walter</creatorcontrib><creatorcontrib>Mink, János</creatorcontrib><creatorcontrib>Kühn, Fritz E.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>European journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goh, Serena L. M.</au><au>Högerl, Manuel P.</au><au>Jokić, Nadežda B.</au><au>Tanase, Alexandrina D.</au><au>Bechlars, Bettina</au><au>Baratta, Walter</au><au>Mink, János</au><au>Kühn, Fritz E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of a Cationic Phthalimido-Functionalized N-Heterocyclic Carbene Complex of Palladium(II) and Its Catalytic Activity</atitle><jtitle>European journal of inorganic chemistry</jtitle><addtitle>Eur. J. Inorg. Chem</addtitle><date>2014-03</date><risdate>2014</risdate><volume>2014</volume><issue>7</issue><spage>1225</spage><epage>1230</epage><pages>1225-1230</pages><issn>1434-1948</issn><eissn>1099-0682</eissn><abstract>A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been synthesized from [3‐methyl‐1‐(2′‐phthalimidoethyl)imidazolium] hexafluorophosphate ([NHCMe,PhtH]PF6) by transmetalation and isolated in 67 % yield. The title complex has been applied as catalyst in the Suzuki–Miyaura cross‐coupling reaction under benign aqueous conditions. The catalyst is active without any observable initiation period. High average turnover frequencies (TOFs) of up to 55000 h–1 have been reached with catalyst concentrations as low as 0.01 mol‐%.
A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been prepared in high yield. The complex was activated instantly, without an initiation period, in the Suzuki–Miyaura cross‐coupling reaction under benign aqueous aerobic conditions. Turnover frequencies (TOFs) up to 55000 h–1, were achieved with 0.01 mol‐% of the complex.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejic.201301277</doi><tpages>6</tpages></addata></record> |
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| subjects | Activated Carbenes Catalysts Catalytic activity Cationic Cross-coupling Homogeneous catalysis N ligands Palladium Synthesis |
| title | Synthesis and Characterization of a Cationic Phthalimido-Functionalized N-Heterocyclic Carbene Complex of Palladium(II) and Its Catalytic Activity |
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