Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts
The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knölker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce...
Gespeichert in:
| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2021-07, Vol.50 (29), p.10102-10112 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 10112 |
|---|---|
| container_issue | 29 |
| container_start_page | 10102 |
| container_title | Dalton transactions : an international journal of inorganic chemistry |
| container_volume | 50 |
| creator | van Slagmaat, Christian A M R Faber, Teresa Chou, Khi Chhay Schwalb Freire, Alfonso J Hadavi, Darya Han, Peiliang Quaedflieg, Peter J L M Verzijl, Gerard K M Alsters, Paul L De Wildeman, Stefaan M A |
| description | The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knölker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, the cis-trans ratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated. |
| doi_str_mv | 10.1039/d1dt01252e |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2550268345</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2550268345</sourcerecordid><originalsourceid>FETCH-LOGICAL-c245t-401385a57ecc41c07494f336c023a9b03b101f2e497ce123e462151360f767493</originalsourceid><addsrcrecordid>eNpdkctu1TAQhq0KRC-w6QMgS92gqgF7bCcnS3R6Q1RiU9aR40x6XBw7tZ1KeSfWvAAvRg49nAWrGf369M1IPyGnnH3kTNSfOt5lxkEBHpAjLquqqEHIV_sdykNynNIjYwBMwRtyKCRIVkF1RH6uNziEhA5Nts9I-xAHnW3wNPTUzMaFQjs7bpbMUO27XRYc9tYvEb8QRWeDS_TZajpGTGmKSDdzF8MD-r1qDBl9ttq5mbY2tDphR0en8_YgHRafmRwmOiXrH-hX__uX-4GxyPOI1Ois3Zxyekte99olfLebJ-T79dX9-ra4-3bzZf35rjAgVS4k42KltKrQGMkNq2QteyFKw0DoumWi5Yz3gLKuDHIQKEvgiouS9VW5wOKEfHjxjjE8TZhyM9hk0DntMUypAaUYlCsh1YKe_Yc-hin65bstpWDFeSkX6vyFMjGkFLFvxmgHHeeGs2bbYXPJL-__dni1wO93yqkdsNuj_0oTfwA_95nu</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2555281164</pqid></control><display><type>article</type><title>Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>van Slagmaat, Christian A M R ; Faber, Teresa ; Chou, Khi Chhay ; Schwalb Freire, Alfonso J ; Hadavi, Darya ; Han, Peiliang ; Quaedflieg, Peter J L M ; Verzijl, Gerard K M ; Alsters, Paul L ; De Wildeman, Stefaan M A</creator><creatorcontrib>van Slagmaat, Christian A M R ; Faber, Teresa ; Chou, Khi Chhay ; Schwalb Freire, Alfonso J ; Hadavi, Darya ; Han, Peiliang ; Quaedflieg, Peter J L M ; Verzijl, Gerard K M ; Alsters, Paul L ; De Wildeman, Stefaan M A</creatorcontrib><description>The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knölker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, the cis-trans ratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/d1dt01252e</identifier><identifier>PMID: 34240727</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Catalysis ; Catalysts ; Cyclopentanes - chemistry ; Dehydration ; Diols ; Hydrogenation ; Iron - chemistry ; Selectivity ; Substrates</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2021-07, Vol.50 (29), p.10102-10112</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c245t-401385a57ecc41c07494f336c023a9b03b101f2e497ce123e462151360f767493</citedby><cites>FETCH-LOGICAL-c245t-401385a57ecc41c07494f336c023a9b03b101f2e497ce123e462151360f767493</cites><orcidid>0000-0001-8373-092X ; 0000-0001-9821-897X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34240727$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>van Slagmaat, Christian A M R</creatorcontrib><creatorcontrib>Faber, Teresa</creatorcontrib><creatorcontrib>Chou, Khi Chhay</creatorcontrib><creatorcontrib>Schwalb Freire, Alfonso J</creatorcontrib><creatorcontrib>Hadavi, Darya</creatorcontrib><creatorcontrib>Han, Peiliang</creatorcontrib><creatorcontrib>Quaedflieg, Peter J L M</creatorcontrib><creatorcontrib>Verzijl, Gerard K M</creatorcontrib><creatorcontrib>Alsters, Paul L</creatorcontrib><creatorcontrib>De Wildeman, Stefaan M A</creatorcontrib><title>Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knölker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, the cis-trans ratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.</description><subject>Catalysis</subject><subject>Catalysts</subject><subject>Cyclopentanes - chemistry</subject><subject>Dehydration</subject><subject>Diols</subject><subject>Hydrogenation</subject><subject>Iron - chemistry</subject><subject>Selectivity</subject><subject>Substrates</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkctu1TAQhq0KRC-w6QMgS92gqgF7bCcnS3R6Q1RiU9aR40x6XBw7tZ1KeSfWvAAvRg49nAWrGf369M1IPyGnnH3kTNSfOt5lxkEBHpAjLquqqEHIV_sdykNynNIjYwBMwRtyKCRIVkF1RH6uNziEhA5Nts9I-xAHnW3wNPTUzMaFQjs7bpbMUO27XRYc9tYvEb8QRWeDS_TZajpGTGmKSDdzF8MD-r1qDBl9ttq5mbY2tDphR0en8_YgHRafmRwmOiXrH-hX__uX-4GxyPOI1Ois3Zxyekte99olfLebJ-T79dX9-ra4-3bzZf35rjAgVS4k42KltKrQGMkNq2QteyFKw0DoumWi5Yz3gLKuDHIQKEvgiouS9VW5wOKEfHjxjjE8TZhyM9hk0DntMUypAaUYlCsh1YKe_Yc-hin65bstpWDFeSkX6vyFMjGkFLFvxmgHHeeGs2bbYXPJL-__dni1wO93yqkdsNuj_0oTfwA_95nu</recordid><startdate>20210727</startdate><enddate>20210727</enddate><creator>van Slagmaat, Christian A M R</creator><creator>Faber, Teresa</creator><creator>Chou, Khi Chhay</creator><creator>Schwalb Freire, Alfonso J</creator><creator>Hadavi, Darya</creator><creator>Han, Peiliang</creator><creator>Quaedflieg, Peter J L M</creator><creator>Verzijl, Gerard K M</creator><creator>Alsters, Paul L</creator><creator>De Wildeman, Stefaan M A</creator><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8373-092X</orcidid><orcidid>https://orcid.org/0000-0001-9821-897X</orcidid></search><sort><creationdate>20210727</creationdate><title>Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts</title><author>van Slagmaat, Christian A M R ; Faber, Teresa ; Chou, Khi Chhay ; Schwalb Freire, Alfonso J ; Hadavi, Darya ; Han, Peiliang ; Quaedflieg, Peter J L M ; Verzijl, Gerard K M ; Alsters, Paul L ; De Wildeman, Stefaan M A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c245t-401385a57ecc41c07494f336c023a9b03b101f2e497ce123e462151360f767493</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Catalysis</topic><topic>Catalysts</topic><topic>Cyclopentanes - chemistry</topic><topic>Dehydration</topic><topic>Diols</topic><topic>Hydrogenation</topic><topic>Iron - chemistry</topic><topic>Selectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>van Slagmaat, Christian A M R</creatorcontrib><creatorcontrib>Faber, Teresa</creatorcontrib><creatorcontrib>Chou, Khi Chhay</creatorcontrib><creatorcontrib>Schwalb Freire, Alfonso J</creatorcontrib><creatorcontrib>Hadavi, Darya</creatorcontrib><creatorcontrib>Han, Peiliang</creatorcontrib><creatorcontrib>Quaedflieg, Peter J L M</creatorcontrib><creatorcontrib>Verzijl, Gerard K M</creatorcontrib><creatorcontrib>Alsters, Paul L</creatorcontrib><creatorcontrib>De Wildeman, Stefaan M A</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</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><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>van Slagmaat, Christian A M R</au><au>Faber, Teresa</au><au>Chou, Khi Chhay</au><au>Schwalb Freire, Alfonso J</au><au>Hadavi, Darya</au><au>Han, Peiliang</au><au>Quaedflieg, Peter J L M</au><au>Verzijl, Gerard K M</au><au>Alsters, Paul L</au><au>De Wildeman, Stefaan M A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2021-07-27</date><risdate>2021</risdate><volume>50</volume><issue>29</issue><spage>10102</spage><epage>10112</epage><pages>10102-10112</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knölker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, the cis-trans ratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>34240727</pmid><doi>10.1039/d1dt01252e</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-8373-092X</orcidid><orcidid>https://orcid.org/0000-0001-9821-897X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2021-07, Vol.50 (29), p.10102-10112 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2550268345 |
| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Catalysis Catalysts Cyclopentanes - chemistry Dehydration Diols Hydrogenation Iron - chemistry Selectivity Substrates |
| title | Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knölker-type catalysts |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-07T01%3A15%3A44IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Chemoselective%20formation%20of%20cyclo-aliphatic%20and%20cyclo-olefinic%201,3-diols%20via%20pressure%20hydrogenation%20of%20potentially%20biobased%20platform%20molecules%20using%20Kn%C3%B6lker-type%20catalysts&rft.jtitle=Dalton%20transactions%20:%20an%20international%20journal%20of%20inorganic%20chemistry&rft.au=van%20Slagmaat,%20Christian%20A%20M%20R&rft.date=2021-07-27&rft.volume=50&rft.issue=29&rft.spage=10102&rft.epage=10112&rft.pages=10102-10112&rft.issn=1477-9226&rft.eissn=1477-9234&rft_id=info:doi/10.1039/d1dt01252e&rft_dat=%3Cproquest_cross%3E2550268345%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2555281164&rft_id=info:pmid/34240727&rfr_iscdi=true |