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Rhodium-Catalyzed Hydroformylation of 1,1-Disubstituted Allenes Employing the Self-Assembling 6-DPPon System
A rhodium‐catalyzed hydroformylation of 1,1‐disubstituted allenes is reported. Using a RhI/6‐DPPon catalyst system, one can obtain β,γ‐unsaturated aldehydes in high regio‐ and chemoselectivity. The Z‐configured product is formed with up to >95 % selectivity when unsymmetrically 1,1‐disubstituted...
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| Published in: | Angewandte Chemie 2015-06, Vol.127 (23), p.7017-7021 |
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| Main Authors: | , |
| Format: | Article |
| Language: | eng ; ger |
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| cited_by | cdi_FETCH-LOGICAL-c2336-af5736989c29b5e0028d7df987290692eb78fa8c449953521c759f5a0f9f06bb3 |
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| cites | cdi_FETCH-LOGICAL-c2336-af5736989c29b5e0028d7df987290692eb78fa8c449953521c759f5a0f9f06bb3 |
| container_end_page | 7021 |
| container_issue | 23 |
| container_start_page | 7017 |
| container_title | Angewandte Chemie |
| container_volume | 127 |
| creator | Köpfer, Alexander Breit, Bernhard |
| description | A rhodium‐catalyzed hydroformylation of 1,1‐disubstituted allenes is reported. Using a RhI/6‐DPPon catalyst system, one can obtain β,γ‐unsaturated aldehydes in high regio‐ and chemoselectivity. The Z‐configured product is formed with up to >95 % selectivity when unsymmetrically 1,1‐disubstituted allenes are submitted to the reaction conditions. This is the first time that these interesting building blocks are accessible by hydroformylation of allenes. The utility of this methodology is demonstrated by further transformations of one of the obtained products.
β,γ‐Ungesättigte Aldehyde werden durch rhodiumkatalysierte Hydroformylierung von 1,1‐disubstituierten Allenen erhalten. Bei unsymmetrisch 1,1‐disubstituierten Allenen wird das Z‐konfigurierte Produkt mit bis zu >95 % Selektivität gebildet. Dies ist die erste Synthese solcher Bausteine durch Hydroformylierung von Allenen. Der Nutzen dieser Methode wurde durch Folgechemie eines der erhaltenen Produkte demonstriert. |
| doi_str_mv | 10.1002/ange.201502086 |
| format | article |
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β,γ‐Ungesättigte Aldehyde werden durch rhodiumkatalysierte Hydroformylierung von 1,1‐disubstituierten Allenen erhalten. Bei unsymmetrisch 1,1‐disubstituierten Allenen wird das Z‐konfigurierte Produkt mit bis zu >95 % Selektivität gebildet. Dies ist die erste Synthese solcher Bausteine durch Hydroformylierung von Allenen. Der Nutzen dieser Methode wurde durch Folgechemie eines der erhaltenen Produkte demonstriert.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201502086</identifier><language>eng ; ger</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Accessibility ; Aldehyde ; Aldehydes ; Allene ; Catalysts ; Chemistry ; Hydroformylierungen ; Methodology ; Rhodium ; Selbstorganisation ; Selectivity ; Transformations ; Utilities</subject><ispartof>Angewandte Chemie, 2015-06, Vol.127 (23), p.7017-7021</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2336-af5736989c29b5e0028d7df987290692eb78fa8c449953521c759f5a0f9f06bb3</citedby><cites>FETCH-LOGICAL-c2336-af5736989c29b5e0028d7df987290692eb78fa8c449953521c759f5a0f9f06bb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Köpfer, Alexander</creatorcontrib><creatorcontrib>Breit, Bernhard</creatorcontrib><title>Rhodium-Catalyzed Hydroformylation of 1,1-Disubstituted Allenes Employing the Self-Assembling 6-DPPon System</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>A rhodium‐catalyzed hydroformylation of 1,1‐disubstituted allenes is reported. Using a RhI/6‐DPPon catalyst system, one can obtain β,γ‐unsaturated aldehydes in high regio‐ and chemoselectivity. The Z‐configured product is formed with up to >95 % selectivity when unsymmetrically 1,1‐disubstituted allenes are submitted to the reaction conditions. This is the first time that these interesting building blocks are accessible by hydroformylation of allenes. The utility of this methodology is demonstrated by further transformations of one of the obtained products.
β,γ‐Ungesättigte Aldehyde werden durch rhodiumkatalysierte Hydroformylierung von 1,1‐disubstituierten Allenen erhalten. Bei unsymmetrisch 1,1‐disubstituierten Allenen wird das Z‐konfigurierte Produkt mit bis zu >95 % Selektivität gebildet. Dies ist die erste Synthese solcher Bausteine durch Hydroformylierung von Allenen. Der Nutzen dieser Methode wurde durch Folgechemie eines der erhaltenen Produkte demonstriert.</description><subject>Accessibility</subject><subject>Aldehyde</subject><subject>Aldehydes</subject><subject>Allene</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Hydroformylierungen</subject><subject>Methodology</subject><subject>Rhodium</subject><subject>Selbstorganisation</subject><subject>Selectivity</subject><subject>Transformations</subject><subject>Utilities</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkU1vEzEQhi0EEqFw5bwSFw44-GP9dYySNEWKStUUcbS8u3br4l0He1ew_HocBVWIC76MZD3PaOYdAN5itMQIkY9muLdLgjBDBEn-DCwwIxhSwcRzsECorqEktXoJXuX8iBDiRKgFCLcPsfNTD9dmNGH-Zbvqau5SdDH1czCjj0MVXYU_YLjxeWry6MdpLNQqBDvYXG37Y4izH-6r8cFWBxscXOVs-yac_jjc3NyUFoc5j7Z_DV44E7J986degC-X27v1Fdx_3n1ar_awJZRyaBwTlCupWqIaZstushOdU1IQhbgithHSGdnWtVKMliVbwZRjBjnlEG8aegHen_seU_w-2Tzq3ufWhmAGG6essUC4PErrgr77B32MUxrKdBpzSSkWkqFCLc9Um2LOyTp9TL43adYY6VP4-hS-fgq_COos_PDBzv-h9ep6t_3bhWfXl8x-PrkmfdNclHPqr9c7TWp22MvNnb6lvwHZbZac</recordid><startdate>20150601</startdate><enddate>20150601</enddate><creator>Köpfer, Alexander</creator><creator>Breit, Bernhard</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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></search><sort><creationdate>20150601</creationdate><title>Rhodium-Catalyzed Hydroformylation of 1,1-Disubstituted Allenes Employing the Self-Assembling 6-DPPon System</title><author>Köpfer, Alexander ; Breit, Bernhard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2336-af5736989c29b5e0028d7df987290692eb78fa8c449953521c759f5a0f9f06bb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng ; ger</language><creationdate>2015</creationdate><topic>Accessibility</topic><topic>Aldehyde</topic><topic>Aldehydes</topic><topic>Allene</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Hydroformylierungen</topic><topic>Methodology</topic><topic>Rhodium</topic><topic>Selbstorganisation</topic><topic>Selectivity</topic><topic>Transformations</topic><topic>Utilities</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Köpfer, Alexander</creatorcontrib><creatorcontrib>Breit, Bernhard</creatorcontrib><collection>Istex</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><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Köpfer, Alexander</au><au>Breit, Bernhard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhodium-Catalyzed Hydroformylation of 1,1-Disubstituted Allenes Employing the Self-Assembling 6-DPPon System</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2015-06-01</date><risdate>2015</risdate><volume>127</volume><issue>23</issue><spage>7017</spage><epage>7021</epage><pages>7017-7021</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>A rhodium‐catalyzed hydroformylation of 1,1‐disubstituted allenes is reported. Using a RhI/6‐DPPon catalyst system, one can obtain β,γ‐unsaturated aldehydes in high regio‐ and chemoselectivity. The Z‐configured product is formed with up to >95 % selectivity when unsymmetrically 1,1‐disubstituted allenes are submitted to the reaction conditions. This is the first time that these interesting building blocks are accessible by hydroformylation of allenes. The utility of this methodology is demonstrated by further transformations of one of the obtained products.
β,γ‐Ungesättigte Aldehyde werden durch rhodiumkatalysierte Hydroformylierung von 1,1‐disubstituierten Allenen erhalten. Bei unsymmetrisch 1,1‐disubstituierten Allenen wird das Z‐konfigurierte Produkt mit bis zu >95 % Selektivität gebildet. Dies ist die erste Synthese solcher Bausteine durch Hydroformylierung von Allenen. Der Nutzen dieser Methode wurde durch Folgechemie eines der erhaltenen Produkte demonstriert.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ange.201502086</doi><tpages>5</tpages></addata></record> |
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| identifier | ISSN: 0044-8249 |
| ispartof | Angewandte Chemie, 2015-06, Vol.127 (23), p.7017-7021 |
| issn | 0044-8249 1521-3757 |
| language | eng ; ger |
| recordid | cdi_proquest_miscellaneous_1701111334 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Accessibility Aldehyde Aldehydes Allene Catalysts Chemistry Hydroformylierungen Methodology Rhodium Selbstorganisation Selectivity Transformations Utilities |
| title | Rhodium-Catalyzed Hydroformylation of 1,1-Disubstituted Allenes Employing the Self-Assembling 6-DPPon System |
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