One-Pot, Selective Hydroformylation, Condensation, and Hydrogenation Processes by a Sol-Gel Entrapped Rhodium Complex, an Immobilized Base, and an Ionic Liquid

We report on a one‐pot, multistep process in which styrene derivatives are selectively hydroformylated to give branched aldehydes, which in turn, are condensed with reactive methylene compounds (malononitrile, ethyl cyanoacetate), and then hydrogenated. The process takes place at 80 °C under 20.7 ba...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:European Journal of Organic Chemistry 2009-04, Vol.2009 (10), p.1502-1505
Hauptverfasser: Hamza, Khalil, Schumann, Herbert, Blum, Jochanan
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1505
container_issue 10
container_start_page 1502
container_title European Journal of Organic Chemistry
container_volume 2009
creator Hamza, Khalil
Schumann, Herbert
Blum, Jochanan
description We report on a one‐pot, multistep process in which styrene derivatives are selectively hydroformylated to give branched aldehydes, which in turn, are condensed with reactive methylene compounds (malononitrile, ethyl cyanoacetate), and then hydrogenated. The process takes place at 80 °C under 20.7 bar H2 and 20.7 bar CO in the presence of [Rh(cod)Cl]2 and Na[Ph2P‐3‐(C6H4SO3)], which have been co‐entrapped within ionic liquid confined silica sol–gel together with a separately encaged base. The catalyst can be reused at least four times, but the base has to be renewed after each run. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) In the presence of [Rh(cod)Cl]2 that has been entrapped within an ionic liquid confined silica sol–gel, styrene derivatives were hydroformylated at 80° C to selectively give branched aldehydes that undergo, withinthe same pot, condensation with active methylene compounds followed by hydrogenation of the resulting unsaturated products.
doi_str_mv 10.1002/ejoc.200801258
format Article
fullrecord <record><control><sourceid>istex_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_ejoc_200801258</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_WNG_7T8L19Z6_F</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3978-a869587c293e4bfffe26d502549edaa361a2c64a81fded3d751a2e1c199964223</originalsourceid><addsrcrecordid>eNqFkM1O3DAURqOqlUopW9bedEcG_yROvKSjYQCNOqiAWrGxPPZNMXXsYIeW9GX6qmQaNOqOle17v3MsfVl2SPCMYEyP4T7oGcW4xoSW9Ztsj2AhcswFfjveC1bkRLDv77MPKd1jjAXnZC_7u_aQX4b-CF2BA93bX4DOBhNDE2I7ONXb4I_QPHgDPr28lDdT5gf4fyN0GYOGlCChzYAUugouX4JDC99H1XVg0Ne7YOxjO4razsHT1oHO2zZsrLN_xv1nlWASbxfBW41W9uHRmo_Zu0a5BAcv5352c7q4np_lq_XyfH6yyjUTVZ2rmouyrjQVDIpN0zRAuSkxLQsBRinGiaKaF6omjQHDTFWOAyCaCCF4QSnbz2aTV8eQUoRGdtG2Kg6SYLmtV27rlbt6R-DTBHQqaeWaqLy2aUdRQotiLH3MiSn32zoYXrHKxcV6_v8f-cTa1MPTjlXxp-QVq0r57ctSVtf1iohbLk_ZM4opnMQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>One-Pot, Selective Hydroformylation, Condensation, and Hydrogenation Processes by a Sol-Gel Entrapped Rhodium Complex, an Immobilized Base, and an Ionic Liquid</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Hamza, Khalil ; Schumann, Herbert ; Blum, Jochanan</creator><creatorcontrib>Hamza, Khalil ; Schumann, Herbert ; Blum, Jochanan</creatorcontrib><description>We report on a one‐pot, multistep process in which styrene derivatives are selectively hydroformylated to give branched aldehydes, which in turn, are condensed with reactive methylene compounds (malononitrile, ethyl cyanoacetate), and then hydrogenated. The process takes place at 80 °C under 20.7 bar H2 and 20.7 bar CO in the presence of [Rh(cod)Cl]2 and Na[Ph2P‐3‐(C6H4SO3)], which have been co‐entrapped within ionic liquid confined silica sol–gel together with a separately encaged base. The catalyst can be reused at least four times, but the base has to be renewed after each run. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2009) In the presence of [Rh(cod)Cl]2 that has been entrapped within an ionic liquid confined silica sol–gel, styrene derivatives were hydroformylated at 80° C to selectively give branched aldehydes that undergo, withinthe same pot, condensation with active methylene compounds followed by hydrogenation of the resulting unsaturated products.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200801258</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Catalysis ; Catalysts: preparations and properties ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Hydroformylation ; Hydrogenation ; Ionic liquids ; Kinetics and mechanisms ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; Reactivity and mechanisms ; Rhodium ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>European Journal of Organic Chemistry, 2009-04, Vol.2009 (10), p.1502-1505</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3978-a869587c293e4bfffe26d502549edaa361a2c64a81fded3d751a2e1c199964223</citedby><cites>FETCH-LOGICAL-c3978-a869587c293e4bfffe26d502549edaa361a2c64a81fded3d751a2e1c199964223</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%2Fejoc.200801258$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200801258$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,776,780,788,1411,27899,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=21244143$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Hamza, Khalil</creatorcontrib><creatorcontrib>Schumann, Herbert</creatorcontrib><creatorcontrib>Blum, Jochanan</creatorcontrib><title>One-Pot, Selective Hydroformylation, Condensation, and Hydrogenation Processes by a Sol-Gel Entrapped Rhodium Complex, an Immobilized Base, and an Ionic Liquid</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>We report on a one‐pot, multistep process in which styrene derivatives are selectively hydroformylated to give branched aldehydes, which in turn, are condensed with reactive methylene compounds (malononitrile, ethyl cyanoacetate), and then hydrogenated. The process takes place at 80 °C under 20.7 bar H2 and 20.7 bar CO in the presence of [Rh(cod)Cl]2 and Na[Ph2P‐3‐(C6H4SO3)], which have been co‐entrapped within ionic liquid confined silica sol–gel together with a separately encaged base. The catalyst can be reused at least four times, but the base has to be renewed after each run. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2009) In the presence of [Rh(cod)Cl]2 that has been entrapped within an ionic liquid confined silica sol–gel, styrene derivatives were hydroformylated at 80° C to selectively give branched aldehydes that undergo, withinthe same pot, condensation with active methylene compounds followed by hydrogenation of the resulting unsaturated products.</description><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Hydroformylation</subject><subject>Hydrogenation</subject><subject>Ionic liquids</subject><subject>Kinetics and mechanisms</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Reactivity and mechanisms</subject><subject>Rhodium</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFkM1O3DAURqOqlUopW9bedEcG_yROvKSjYQCNOqiAWrGxPPZNMXXsYIeW9GX6qmQaNOqOle17v3MsfVl2SPCMYEyP4T7oGcW4xoSW9Ztsj2AhcswFfjveC1bkRLDv77MPKd1jjAXnZC_7u_aQX4b-CF2BA93bX4DOBhNDE2I7ONXb4I_QPHgDPr28lDdT5gf4fyN0GYOGlCChzYAUugouX4JDC99H1XVg0Ne7YOxjO4razsHT1oHO2zZsrLN_xv1nlWASbxfBW41W9uHRmo_Zu0a5BAcv5352c7q4np_lq_XyfH6yyjUTVZ2rmouyrjQVDIpN0zRAuSkxLQsBRinGiaKaF6omjQHDTFWOAyCaCCF4QSnbz2aTV8eQUoRGdtG2Kg6SYLmtV27rlbt6R-DTBHQqaeWaqLy2aUdRQotiLH3MiSn32zoYXrHKxcV6_v8f-cTa1MPTjlXxp-QVq0r57ctSVtf1iohbLk_ZM4opnMQ</recordid><startdate>200904</startdate><enddate>200904</enddate><creator>Hamza, Khalil</creator><creator>Schumann, Herbert</creator><creator>Blum, Jochanan</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200904</creationdate><title>One-Pot, Selective Hydroformylation, Condensation, and Hydrogenation Processes by a Sol-Gel Entrapped Rhodium Complex, an Immobilized Base, and an Ionic Liquid</title><author>Hamza, Khalil ; Schumann, Herbert ; Blum, Jochanan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3978-a869587c293e4bfffe26d502549edaa361a2c64a81fded3d751a2e1c199964223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Hydroformylation</topic><topic>Hydrogenation</topic><topic>Ionic liquids</topic><topic>Kinetics and mechanisms</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Reactivity and mechanisms</topic><topic>Rhodium</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hamza, Khalil</creatorcontrib><creatorcontrib>Schumann, Herbert</creatorcontrib><creatorcontrib>Blum, Jochanan</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hamza, Khalil</au><au>Schumann, Herbert</au><au>Blum, Jochanan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-Pot, Selective Hydroformylation, Condensation, and Hydrogenation Processes by a Sol-Gel Entrapped Rhodium Complex, an Immobilized Base, and an Ionic Liquid</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2009-04</date><risdate>2009</risdate><volume>2009</volume><issue>10</issue><spage>1502</spage><epage>1505</epage><pages>1502-1505</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>We report on a one‐pot, multistep process in which styrene derivatives are selectively hydroformylated to give branched aldehydes, which in turn, are condensed with reactive methylene compounds (malononitrile, ethyl cyanoacetate), and then hydrogenated. The process takes place at 80 °C under 20.7 bar H2 and 20.7 bar CO in the presence of [Rh(cod)Cl]2 and Na[Ph2P‐3‐(C6H4SO3)], which have been co‐entrapped within ionic liquid confined silica sol–gel together with a separately encaged base. The catalyst can be reused at least four times, but the base has to be renewed after each run. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2009) In the presence of [Rh(cod)Cl]2 that has been entrapped within an ionic liquid confined silica sol–gel, styrene derivatives were hydroformylated at 80° C to selectively give branched aldehydes that undergo, withinthe same pot, condensation with active methylene compounds followed by hydrogenation of the resulting unsaturated products.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200801258</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1434-193X
ispartof European Journal of Organic Chemistry, 2009-04, Vol.2009 (10), p.1502-1505
issn 1434-193X
1099-0690
language eng
recordid cdi_crossref_primary_10_1002_ejoc_200801258
source Wiley Online Library Journals Frontfile Complete
subjects Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Hydroformylation
Hydrogenation
Ionic liquids
Kinetics and mechanisms
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Rhodium
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
title One-Pot, Selective Hydroformylation, Condensation, and Hydrogenation Processes by a Sol-Gel Entrapped Rhodium Complex, an Immobilized Base, and an Ionic Liquid
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-09T03%3A59%3A07IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=One-Pot,%20Selective%20Hydroformylation,%20Condensation,%20and%20Hydrogenation%20Processes%20by%20a%20Sol-Gel%20Entrapped%20Rhodium%20Complex,%20an%20Immobilized%20Base,%20and%20an%20Ionic%20Liquid&rft.jtitle=European%20Journal%20of%20Organic%20Chemistry&rft.au=Hamza,%20Khalil&rft.date=2009-04&rft.volume=2009&rft.issue=10&rft.spage=1502&rft.epage=1505&rft.pages=1502-1505&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.200801258&rft_dat=%3Cistex_cross%3Eark_67375_WNG_7T8L19Z6_F%3C/istex_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true