An improved practical Pd/C-catalyzed Sonogashira cross-coupling reaction for the synthesis of liquid crystals of trans-cyclohexyltolans
An improved practical synthesis of liquid crystals of trans‐cyclohexyltolans by Sonogashira cross‐coupling reaction of 1‐iodo‐4‐(trans‐4‐alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C (palladium on activated carbon) as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixt...
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| Veröffentlicht in: | Applied organometallic chemistry 2010-06, Vol.24 (6), p.473-476 |
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| container_end_page | 476 |
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| container_issue | 6 |
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| container_title | Applied organometallic chemistry |
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| creator | Shang, Hongyong Hua, Ruimao Zheng, Qingwei Zhang, Jianli Liang, Xiao Zhu, Qiming |
| description | An improved practical synthesis of liquid crystals of trans‐cyclohexyltolans by Sonogashira cross‐coupling reaction of 1‐iodo‐4‐(trans‐4‐alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C (palladium on activated carbon) as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixture solvent of acetone–water (5:2 in volume) is described. The liquid crystals could be obtained in high yields as a solid with excellent purity by simple filtration, and the filtrate could be reused several times while still retaining high catalytic activity. Copyright © 2010 John Wiley & Sons, Ltd.
Liquid crystals of trans‐cyclohexyltolans were synthesized in high yields by Sonogashira cross‐coupling reaction of 1‐iodo‐4‐(trans‐4‐alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixture solvent of acetone–water (5:2 in volume). |
| doi_str_mv | 10.1002/aoc.1642 |
| format | Article |
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Liquid crystals of trans‐cyclohexyltolans were synthesized in high yields by Sonogashira cross‐coupling reaction of 1‐iodo‐4‐(trans‐4‐alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixture solvent of acetone–water (5:2 in volume).</description><identifier>ISSN: 0268-2605</identifier><identifier>EISSN: 1099-0739</identifier><identifier>DOI: 10.1002/aoc.1642</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>Alkynes ; cross-coupling reaction ; cuprous iodide ; cyclohexyltolans ; Filtration ; Liquid crystals ; Metalorganic compounds ; Palladium ; Pd/C ; Solvents ; Synthesis ; Terminals</subject><ispartof>Applied organometallic chemistry, 2010-06, Vol.24 (6), p.473-476</ispartof><rights>Copyright © 2010 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3352-598a55e7cb2cc0165af62e9b5938b233e5c5ad4b345aeaa8fd537e556f6de303</citedby><cites>FETCH-LOGICAL-c3352-598a55e7cb2cc0165af62e9b5938b233e5c5ad4b345aeaa8fd537e556f6de303</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%2Faoc.1642$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Faoc.1642$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Shang, Hongyong</creatorcontrib><creatorcontrib>Hua, Ruimao</creatorcontrib><creatorcontrib>Zheng, Qingwei</creatorcontrib><creatorcontrib>Zhang, Jianli</creatorcontrib><creatorcontrib>Liang, Xiao</creatorcontrib><creatorcontrib>Zhu, Qiming</creatorcontrib><title>An improved practical Pd/C-catalyzed Sonogashira cross-coupling reaction for the synthesis of liquid crystals of trans-cyclohexyltolans</title><title>Applied organometallic chemistry</title><addtitle>Appl. Organometal. Chem</addtitle><description>An improved practical synthesis of liquid crystals of trans‐cyclohexyltolans by Sonogashira cross‐coupling reaction of 1‐iodo‐4‐(trans‐4‐alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C (palladium on activated carbon) as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixture solvent of acetone–water (5:2 in volume) is described. The liquid crystals could be obtained in high yields as a solid with excellent purity by simple filtration, and the filtrate could be reused several times while still retaining high catalytic activity. Copyright © 2010 John Wiley & Sons, Ltd.
Liquid crystals of trans‐cyclohexyltolans were synthesized in high yields by Sonogashira cross‐coupling reaction of 1‐iodo‐4‐(trans‐4‐alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixture solvent of acetone–water (5:2 in volume).</description><subject>Alkynes</subject><subject>cross-coupling reaction</subject><subject>cuprous iodide</subject><subject>cyclohexyltolans</subject><subject>Filtration</subject><subject>Liquid crystals</subject><subject>Metalorganic compounds</subject><subject>Palladium</subject><subject>Pd/C</subject><subject>Solvents</subject><subject>Synthesis</subject><subject>Terminals</subject><issn>0268-2605</issn><issn>1099-0739</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp1kM1KAzEUhYMoWH_AR8hON6OZZJKZLEvRKooKCgU3Ic3csdF0UpOpOr6Ar21qRXDh6sC93zncexA6yMlxTgg90d4c56KgG2iQEykzUjK5iQaEiiqjgvBttBPjEyFEirwYoM9hi-18Efwr1HgRtOms0Q7f1iejzOhOu_4jLe586x91nNmgsQk-xsz45cLZ9hEHWHl8ixsfcDcDHPs2SbQR-wY7-7K0dfL0MWV9j7qg2-TvjfMzeO9d510a7KGtJgGw_6O76P7s9H50nl3djC9Gw6vMMMZpxmWlOYfSTKkxJBdcN4KCnHLJqillDLjhui6mrOAatK6amrMSOBeNqIERtosO17Hp45clxE7NbTTg0gngl1GVnIlKFpQn8mhNfv8boFGLYOc69ConatW0Sk2rVdMJzdbom3XQ_8up4c3oL29jB--_vA7PSpSs5GpyPVYPsji_lZcTNWFfgQCSLg</recordid><startdate>201006</startdate><enddate>201006</enddate><creator>Shang, Hongyong</creator><creator>Hua, Ruimao</creator><creator>Zheng, Qingwei</creator><creator>Zhang, Jianli</creator><creator>Liang, Xiao</creator><creator>Zhu, Qiming</creator><general>John Wiley & Sons, Ltd</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>201006</creationdate><title>An improved practical Pd/C-catalyzed Sonogashira cross-coupling reaction for the synthesis of liquid crystals of trans-cyclohexyltolans</title><author>Shang, Hongyong ; Hua, Ruimao ; Zheng, Qingwei ; Zhang, Jianli ; Liang, Xiao ; Zhu, Qiming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3352-598a55e7cb2cc0165af62e9b5938b233e5c5ad4b345aeaa8fd537e556f6de303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alkynes</topic><topic>cross-coupling reaction</topic><topic>cuprous iodide</topic><topic>cyclohexyltolans</topic><topic>Filtration</topic><topic>Liquid crystals</topic><topic>Metalorganic compounds</topic><topic>Palladium</topic><topic>Pd/C</topic><topic>Solvents</topic><topic>Synthesis</topic><topic>Terminals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shang, Hongyong</creatorcontrib><creatorcontrib>Hua, Ruimao</creatorcontrib><creatorcontrib>Zheng, Qingwei</creatorcontrib><creatorcontrib>Zhang, Jianli</creatorcontrib><creatorcontrib>Liang, Xiao</creatorcontrib><creatorcontrib>Zhu, Qiming</creatorcontrib><collection>Istex</collection><collection>CrossRef</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>Applied organometallic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shang, Hongyong</au><au>Hua, Ruimao</au><au>Zheng, Qingwei</au><au>Zhang, Jianli</au><au>Liang, Xiao</au><au>Zhu, Qiming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An improved practical Pd/C-catalyzed Sonogashira cross-coupling reaction for the synthesis of liquid crystals of trans-cyclohexyltolans</atitle><jtitle>Applied organometallic chemistry</jtitle><addtitle>Appl. Organometal. Chem</addtitle><date>2010-06</date><risdate>2010</risdate><volume>24</volume><issue>6</issue><spage>473</spage><epage>476</epage><pages>473-476</pages><issn>0268-2605</issn><eissn>1099-0739</eissn><abstract>An improved practical synthesis of liquid crystals of trans‐cyclohexyltolans by Sonogashira cross‐coupling reaction of 1‐iodo‐4‐(trans‐4‐alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C (palladium on activated carbon) as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixture solvent of acetone–water (5:2 in volume) is described. The liquid crystals could be obtained in high yields as a solid with excellent purity by simple filtration, and the filtrate could be reused several times while still retaining high catalytic activity. Copyright © 2010 John Wiley & Sons, Ltd.
Liquid crystals of trans‐cyclohexyltolans were synthesized in high yields by Sonogashira cross‐coupling reaction of 1‐iodo‐4‐(trans‐4‐alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixture solvent of acetone–water (5:2 in volume).</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/aoc.1642</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0268-2605 |
| ispartof | Applied organometallic chemistry, 2010-06, Vol.24 (6), p.473-476 |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkynes cross-coupling reaction cuprous iodide cyclohexyltolans Filtration Liquid crystals Metalorganic compounds Palladium Pd/C Solvents Synthesis Terminals |
| title | An improved practical Pd/C-catalyzed Sonogashira cross-coupling reaction for the synthesis of liquid crystals of trans-cyclohexyltolans |
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