Highly active organosilane-based N-heterocyclic carbene-palladium complex immobilized on silica particles for the Suzuki reaction
1-Methyl-3-(3-trimethoxysilylpropyl)imidazolium chloride, [TMSPIM][Cl ], was synthesized as a precursor of -heterocyclic carbene (NHC), which can be coordinated with palladium to give an organosilane-based bidentic NHC-Pd complex. The organosilane-based NHC-Pd complex was immobilized covalently on s...
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| Veröffentlicht in: | Pure and applied chemistry 2007-09, Vol.79 (9), p.1553-1559 |
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| container_title | Pure and applied chemistry |
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| creator | Lee, Sang-Myung Yoon, Hyo-Jin Kim, Jong-Ho Chung, Woo-Jae Lee, Yoon-Sik |
| description | 1-Methyl-3-(3-trimethoxysilylpropyl)imidazolium chloride, [TMSPIM][Cl
], was synthesized as a precursor of
-heterocyclic carbene (NHC), which can be coordinated with palladium to give an organosilane-based bidentic NHC-Pd complex. The organosilane-based NHC-Pd complex was immobilized covalently on silica particles (NHC-Pd/silica) and then characterized by field emission/scanning electron microscopy (FE/SEM), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIRS), and inductively coupled plasma/atomic emission spectroscopy (ICP/AES). The Suzuki reaction was performed as a model reaction to examine the catalytic activity of NHC-Pd/silica. NHC-Pd/silica exhibited excellent performance in the Suzuki reaction of various aryl halide derivatives (except for aryl chloride derivatives) with phenylboronic acid
(room temperature and short reaction time). Moreover, the catalyst was recycled several times without any significant loss of catalytic activity in the Suzuki reaction. |
| doi_str_mv | 10.1351/pac200779091553 |
| format | Article |
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], was synthesized as a precursor of
-heterocyclic carbene (NHC), which can be coordinated with palladium to give an organosilane-based bidentic NHC-Pd complex. The organosilane-based NHC-Pd complex was immobilized covalently on silica particles (NHC-Pd/silica) and then characterized by field emission/scanning electron microscopy (FE/SEM), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIRS), and inductively coupled plasma/atomic emission spectroscopy (ICP/AES). The Suzuki reaction was performed as a model reaction to examine the catalytic activity of NHC-Pd/silica. NHC-Pd/silica exhibited excellent performance in the Suzuki reaction of various aryl halide derivatives (except for aryl chloride derivatives) with phenylboronic acid
(room temperature and short reaction time). Moreover, the catalyst was recycled several times without any significant loss of catalytic activity in the Suzuki reaction.</description><identifier>ISSN: 0033-4545</identifier><identifier>EISSN: 1365-3075</identifier><identifier>DOI: 10.1351/pac200779091553</identifier><language>eng</language><publisher>Berlin: De Gruyter</publisher><subject>Aromatic compounds ; Atomic beam spectroscopy ; Catalysis ; Catalytic activity ; Chemical reactions ; Derivatives ; Field emission microscopy ; Fourier transforms ; Inductively coupled plasma ; Microscopes ; Microscopy ; N-heterocyclic carbene ; organosilane ; Palladium ; Reaction time ; Scanning electron microscopy ; silica ; Silicon dioxide ; Spectrum analysis ; Suzuki reaction ; Transmission electron microscopy</subject><ispartof>Pure and applied chemistry, 2007-09, Vol.79 (9), p.1553-1559</ispartof><rights>2013 Walter de Gruyter GmbH, Berlin/Boston</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c431t-39d3677e8ea634a221be4735f66cbb32e123c9c117c4f4b426743412b0a37e1d3</citedby><cites>FETCH-LOGICAL-c431t-39d3677e8ea634a221be4735f66cbb32e123c9c117c4f4b426743412b0a37e1d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Lee, Sang-Myung</creatorcontrib><creatorcontrib>Yoon, Hyo-Jin</creatorcontrib><creatorcontrib>Kim, Jong-Ho</creatorcontrib><creatorcontrib>Chung, Woo-Jae</creatorcontrib><creatorcontrib>Lee, Yoon-Sik</creatorcontrib><title>Highly active organosilane-based N-heterocyclic carbene-palladium complex immobilized on silica particles for the Suzuki reaction</title><title>Pure and applied chemistry</title><description>1-Methyl-3-(3-trimethoxysilylpropyl)imidazolium chloride, [TMSPIM][Cl
], was synthesized as a precursor of
-heterocyclic carbene (NHC), which can be coordinated with palladium to give an organosilane-based bidentic NHC-Pd complex. The organosilane-based NHC-Pd complex was immobilized covalently on silica particles (NHC-Pd/silica) and then characterized by field emission/scanning electron microscopy (FE/SEM), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIRS), and inductively coupled plasma/atomic emission spectroscopy (ICP/AES). The Suzuki reaction was performed as a model reaction to examine the catalytic activity of NHC-Pd/silica. NHC-Pd/silica exhibited excellent performance in the Suzuki reaction of various aryl halide derivatives (except for aryl chloride derivatives) with phenylboronic acid
(room temperature and short reaction time). Moreover, the catalyst was recycled several times without any significant loss of catalytic activity in the Suzuki reaction.</description><subject>Aromatic compounds</subject><subject>Atomic beam spectroscopy</subject><subject>Catalysis</subject><subject>Catalytic activity</subject><subject>Chemical reactions</subject><subject>Derivatives</subject><subject>Field emission microscopy</subject><subject>Fourier transforms</subject><subject>Inductively coupled plasma</subject><subject>Microscopes</subject><subject>Microscopy</subject><subject>N-heterocyclic carbene</subject><subject>organosilane</subject><subject>Palladium</subject><subject>Reaction time</subject><subject>Scanning electron microscopy</subject><subject>silica</subject><subject>Silicon dioxide</subject><subject>Spectrum analysis</subject><subject>Suzuki reaction</subject><subject>Transmission electron microscopy</subject><issn>0033-4545</issn><issn>1365-3075</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNp1kE1LxDAQhoMouK6evQY8V5NM0tiLIOIXiB7Uc0nT6W40bWrSquvNf25lBUHwNAMzz_PCS8g-Z4ccFD_qjRWMaV2wgisFG2TGIVcZMK02yYwxgEwqqbbJTkpPjDFZSDEjn1dusfQrauzgXpGGuDBdSM6bDrPKJKzpbbbEAWOwK-udpdbECqdjb7w3tRtbakPbe3ynrm1D5bz7mKDQ0UnirKG9iYOzHhNtQqTDEun9-DE-OxrxOzN0u2SrMT7h3s-ck8eL84ezq-zm7vL67PQmsxL4kEFRQ641HqPJQRoheIVSg2ry3FYVCOQCbGE511Y2spIi1xIkFxUzoJHXMCcHa28fw8uIaSifwhi7KbIUAhio_HhSzMnR-svGkFLEpuyja01clZyV3z2Xf3qeiJM18Wb81FONiziupuVX_w-pi7XgC1wahj8</recordid><startdate>20070901</startdate><enddate>20070901</enddate><creator>Lee, Sang-Myung</creator><creator>Yoon, Hyo-Jin</creator><creator>Kim, Jong-Ho</creator><creator>Chung, Woo-Jae</creator><creator>Lee, Yoon-Sik</creator><general>De Gruyter</general><general>Walter de Gruyter GmbH</general><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope></search><sort><creationdate>20070901</creationdate><title>Highly active organosilane-based N-heterocyclic carbene-palladium complex immobilized on silica particles for the Suzuki reaction</title><author>Lee, Sang-Myung ; Yoon, Hyo-Jin ; Kim, Jong-Ho ; Chung, Woo-Jae ; Lee, Yoon-Sik</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c431t-39d3677e8ea634a221be4735f66cbb32e123c9c117c4f4b426743412b0a37e1d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Aromatic compounds</topic><topic>Atomic beam spectroscopy</topic><topic>Catalysis</topic><topic>Catalytic activity</topic><topic>Chemical reactions</topic><topic>Derivatives</topic><topic>Field emission microscopy</topic><topic>Fourier transforms</topic><topic>Inductively coupled plasma</topic><topic>Microscopes</topic><topic>Microscopy</topic><topic>N-heterocyclic carbene</topic><topic>organosilane</topic><topic>Palladium</topic><topic>Reaction time</topic><topic>Scanning electron microscopy</topic><topic>silica</topic><topic>Silicon dioxide</topic><topic>Spectrum analysis</topic><topic>Suzuki reaction</topic><topic>Transmission electron microscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Sang-Myung</creatorcontrib><creatorcontrib>Yoon, Hyo-Jin</creatorcontrib><creatorcontrib>Kim, Jong-Ho</creatorcontrib><creatorcontrib>Chung, Woo-Jae</creatorcontrib><creatorcontrib>Lee, Yoon-Sik</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Pure and applied chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Sang-Myung</au><au>Yoon, Hyo-Jin</au><au>Kim, Jong-Ho</au><au>Chung, Woo-Jae</au><au>Lee, Yoon-Sik</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly active organosilane-based N-heterocyclic carbene-palladium complex immobilized on silica particles for the Suzuki reaction</atitle><jtitle>Pure and applied chemistry</jtitle><date>2007-09-01</date><risdate>2007</risdate><volume>79</volume><issue>9</issue><spage>1553</spage><epage>1559</epage><pages>1553-1559</pages><issn>0033-4545</issn><eissn>1365-3075</eissn><abstract>1-Methyl-3-(3-trimethoxysilylpropyl)imidazolium chloride, [TMSPIM][Cl
], was synthesized as a precursor of
-heterocyclic carbene (NHC), which can be coordinated with palladium to give an organosilane-based bidentic NHC-Pd complex. The organosilane-based NHC-Pd complex was immobilized covalently on silica particles (NHC-Pd/silica) and then characterized by field emission/scanning electron microscopy (FE/SEM), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIRS), and inductively coupled plasma/atomic emission spectroscopy (ICP/AES). The Suzuki reaction was performed as a model reaction to examine the catalytic activity of NHC-Pd/silica. NHC-Pd/silica exhibited excellent performance in the Suzuki reaction of various aryl halide derivatives (except for aryl chloride derivatives) with phenylboronic acid
(room temperature and short reaction time). Moreover, the catalyst was recycled several times without any significant loss of catalytic activity in the Suzuki reaction.</abstract><cop>Berlin</cop><pub>De Gruyter</pub><doi>10.1351/pac200779091553</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Aromatic compounds Atomic beam spectroscopy Catalysis Catalytic activity Chemical reactions Derivatives Field emission microscopy Fourier transforms Inductively coupled plasma Microscopes Microscopy N-heterocyclic carbene organosilane Palladium Reaction time Scanning electron microscopy silica Silicon dioxide Spectrum analysis Suzuki reaction Transmission electron microscopy |
| title | Highly active organosilane-based N-heterocyclic carbene-palladium complex immobilized on silica particles for the Suzuki reaction |
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