Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water
A concise synthesis of two imidazolium ion-tagged prolinamide organocatalysts 3 and 4, varying in anionic component (CF 3 COO − and PF 6 − , respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The...
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| Veröffentlicht in: | Catalysis letters 2016, Vol.146 (1), p.212-219 |
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| creator | Eyckens, Daniel J. Brozinski, Hannah L. Delaney, Joshua P. Servinis, Linden Naghashian, Sahar Henderson, Luke C. |
| description | A concise synthesis of two imidazolium ion-tagged prolinamide organocatalysts 3 and 4, varying in anionic component (CF
3
COO
−
and PF
6
−
, respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The efficiency of each catalyst was compared via a direct aldol reaction revealing a large contrast in catalytic performance, with the catalyst bearing the PF
6
−
anion being superior. The optimal conditions were determined to be an on-water reaction system, and substrate scoping gave a range of desired aldol products in high conversion (up to >99 %), dr (up to 98:2), and er (up to 96:4). The application of these catalysts to beta-nitrostyrene conjugate addition is also presented.
Graphical Abstract |
| doi_str_mv | 10.1007/s10562-015-1630-4 |
| format | Article |
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3
COO
−
and PF
6
−
, respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The efficiency of each catalyst was compared via a direct aldol reaction revealing a large contrast in catalytic performance, with the catalyst bearing the PF
6
−
anion being superior. The optimal conditions were determined to be an on-water reaction system, and substrate scoping gave a range of desired aldol products in high conversion (up to >99 %), dr (up to 98:2), and er (up to 96:4). The application of these catalysts to beta-nitrostyrene conjugate addition is also presented.
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3
COO
−
and PF
6
−
, respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The efficiency of each catalyst was compared via a direct aldol reaction revealing a large contrast in catalytic performance, with the catalyst bearing the PF
6
−
anion being superior. The optimal conditions were determined to be an on-water reaction system, and substrate scoping gave a range of desired aldol products in high conversion (up to >99 %), dr (up to 98:2), and er (up to 96:4). The application of these catalysts to beta-nitrostyrene conjugate addition is also presented.
Graphical Abstract</description><subject>Aldehydes</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Comparative analysis</subject><subject>Glass transition temperature</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Ionic liquids</subject><subject>Melting points</subject><subject>Organometallic Chemistry</subject><subject>Physical Chemistry</subject><subject>Substrates</subject><subject>Surface active agents</subject><issn>1011-372X</issn><issn>1572-879X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNp1kUFLHTEQx5fSQq31A_S24MlDdJJNsrvHh7b6QHnFKvUWZrOz68q-xCZ5UL-9kRXEg6cZht9vZuBfFD84HHOA-iRyUFow4IpxXQGTn4o9rmrBmrq9-5x74JxVtbj7WnyL8QEA2pq3e8XV2jt2g-NIffk7-HlyuJ16KjdhROctJpyfYorl4EOZ7qk8mwLZVK7m3s_lNaFNk3flxrG_mCh8L74MOEc6eK37xe2vnzenF-xyc74-XV0yK4VOjGwDVHHd9LUehNUgoFcVdI1Eiwq7vlNUi77jDRGoQaMQthtEmw2OVqlqvzhc9j4G_29HMZkHvwsunzRCgpZStbLK1PFCjTiTmdzgU8gHLPa0nax3NEx5vpJSNK2odJ2Fo3dCZhL9TyPuYjTrP9fvWb6wNvgYAw3mMUxbDE-Gg3mJxCyRmByJeYnEyOyIxYmZdSOFt7c_lp4BLZyM1Q</recordid><startdate>2016</startdate><enddate>2016</enddate><creator>Eyckens, Daniel J.</creator><creator>Brozinski, Hannah L.</creator><creator>Delaney, Joshua P.</creator><creator>Servinis, Linden</creator><creator>Naghashian, Sahar</creator><creator>Henderson, Luke C.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>ISR</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope></search><sort><creationdate>2016</creationdate><title>Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water</title><author>Eyckens, Daniel J. ; Brozinski, Hannah L. ; Delaney, Joshua P. ; Servinis, Linden ; Naghashian, Sahar ; Henderson, Luke C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c426t-ec80e3168d76f2c6020d530b84aca5abdb5e72db18ee05f6a22cbf291681ac553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Aldehydes</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Comparative analysis</topic><topic>Glass transition temperature</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Ionic liquids</topic><topic>Melting points</topic><topic>Organometallic Chemistry</topic><topic>Physical Chemistry</topic><topic>Substrates</topic><topic>Surface active agents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Eyckens, Daniel J.</creatorcontrib><creatorcontrib>Brozinski, Hannah L.</creatorcontrib><creatorcontrib>Delaney, Joshua P.</creatorcontrib><creatorcontrib>Servinis, Linden</creatorcontrib><creatorcontrib>Naghashian, Sahar</creatorcontrib><creatorcontrib>Henderson, Luke C.</creatorcontrib><collection>CrossRef</collection><collection>Gale In Context: Science</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><jtitle>Catalysis letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Eyckens, Daniel J.</au><au>Brozinski, Hannah L.</au><au>Delaney, Joshua P.</au><au>Servinis, Linden</au><au>Naghashian, Sahar</au><au>Henderson, Luke C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water</atitle><jtitle>Catalysis letters</jtitle><stitle>Catal Lett</stitle><date>2016</date><risdate>2016</risdate><volume>146</volume><issue>1</issue><spage>212</spage><epage>219</epage><pages>212-219</pages><issn>1011-372X</issn><eissn>1572-879X</eissn><abstract>A concise synthesis of two imidazolium ion-tagged prolinamide organocatalysts 3 and 4, varying in anionic component (CF
3
COO
−
and PF
6
−
, respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The efficiency of each catalyst was compared via a direct aldol reaction revealing a large contrast in catalytic performance, with the catalyst bearing the PF
6
−
anion being superior. The optimal conditions were determined to be an on-water reaction system, and substrate scoping gave a range of desired aldol products in high conversion (up to >99 %), dr (up to 98:2), and er (up to 96:4). The application of these catalysts to beta-nitrostyrene conjugate addition is also presented.
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| language | eng |
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| source | SpringerLink Journals |
| subjects | Aldehydes Catalysis Catalysts Chemical synthesis Chemistry Chemistry and Materials Science Comparative analysis Glass transition temperature Industrial Chemistry/Chemical Engineering Ionic liquids Melting points Organometallic Chemistry Physical Chemistry Substrates Surface active agents |
| title | Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water |
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