Rhodium-Catalyzed Hydrogenation of Alkenes by Rhodium/Tris(fluoroalkoxy)phosphane Complexes in Fluorous Biphasic System
The reaction of [Ir(μ‐Cl)(COD)]2 with various fluorous derivatives of triphenylphosphane containing a para‐, meta‐, or ortho‐(1H,1H‐perfluoroalkoxy)‐substituted fluorous phosphane P(C6H4‐ORf)3 (Rf=CH2C7F15, CH2CH2CH2C8F17) and CO (1 atm) gives the corresponding trans‐[Ir(μ‐Cl)(CO){P(C6H4ORf)3}2]. Th...
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Veröffentlicht in: | Advanced synthesis & catalysis 2003-05, Vol.345 (5), p.603-611 |
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description | The reaction of [Ir(μ‐Cl)(COD)]2 with various fluorous derivatives of triphenylphosphane containing a para‐, meta‐, or ortho‐(1H,1H‐perfluoroalkoxy)‐substituted fluorous phosphane P(C6H4‐ORf)3 (Rf=CH2C7F15, CH2CH2CH2C8F17) and CO (1 atm) gives the corresponding trans‐[Ir(μ‐Cl)(CO){P(C6H4ORf)3}2]. The IR νCO values of these complexes give some information on the donor/acceptor properties of the phosphanes. These fluorous derivatives of triphenylphosphane, as well as a phosphane bearing two (1H,1H‐perfluoroalkyloxy) chains at the 3,5‐positions, were used in association with [Rh(μ‐Cl)(COD)]2 or [Rh(COD)2]PF6 in the reduction of methyl cinnamate, 2‐cyclohexen‐1‐one, cinnamaldehyde, and methyl α‐acetamidocinnamate in a two‐phase system D‐100/ethanol under 1 bar hydrogen at room temperature. Some differences in catalytic activity were observed in the reduction of methyl cinnamate, the most active catalyst being the rhodium complex containing the phosphane with the p‐fluorous ponytail. Recycling of the fluorous catalyst was possible, particularly using the p‐substituted phosphane, where no significant loss of catalyst or activity was observed, and generally with very low leaching of rhodium or phosphane in the organic phase. |
doi_str_mv | 10.1002/adsc.200202122 |
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The IR νCO values of these complexes give some information on the donor/acceptor properties of the phosphanes. These fluorous derivatives of triphenylphosphane, as well as a phosphane bearing two (1H,1H‐perfluoroalkyloxy) chains at the 3,5‐positions, were used in association with [Rh(μ‐Cl)(COD)]2 or [Rh(COD)2]PF6 in the reduction of methyl cinnamate, 2‐cyclohexen‐1‐one, cinnamaldehyde, and methyl α‐acetamidocinnamate in a two‐phase system D‐100/ethanol under 1 bar hydrogen at room temperature. Some differences in catalytic activity were observed in the reduction of methyl cinnamate, the most active catalyst being the rhodium complex containing the phosphane with the p‐fluorous ponytail. Recycling of the fluorous catalyst was possible, particularly using the p‐substituted phosphane, where no significant loss of catalyst or activity was observed, and generally with very low leaching of rhodium or phosphane in the organic phase.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.200202122</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>biphasic catalysis ; catalyst recycling ; fluorous ; hydrogenation ; iridium ; rhodium</subject><ispartof>Advanced synthesis & catalysis, 2003-05, Vol.345 (5), p.603-611</ispartof><rights>2003 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3912-4a7d15c1212d665a57e2ed8c513872fe040074edb06f97f7d4a916f31f22db63</citedby><cites>FETCH-LOGICAL-c3912-4a7d15c1212d665a57e2ed8c513872fe040074edb06f97f7d4a916f31f22db63</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%2Fadsc.200202122$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.200202122$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Sinou, Denis</creatorcontrib><creatorcontrib>Maillard, David</creatorcontrib><creatorcontrib>Aghmiz, Ali</creatorcontrib><creatorcontrib>Masdeu i-Bultó, Anna M.</creatorcontrib><title>Rhodium-Catalyzed Hydrogenation of Alkenes by Rhodium/Tris(fluoroalkoxy)phosphane Complexes in Fluorous Biphasic System</title><title>Advanced synthesis & catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>The reaction of [Ir(μ‐Cl)(COD)]2 with various fluorous derivatives of triphenylphosphane containing a para‐, meta‐, or ortho‐(1H,1H‐perfluoroalkoxy)‐substituted fluorous phosphane P(C6H4‐ORf)3 (Rf=CH2C7F15, CH2CH2CH2C8F17) and CO (1 atm) gives the corresponding trans‐[Ir(μ‐Cl)(CO){P(C6H4ORf)3}2]. The IR νCO values of these complexes give some information on the donor/acceptor properties of the phosphanes. These fluorous derivatives of triphenylphosphane, as well as a phosphane bearing two (1H,1H‐perfluoroalkyloxy) chains at the 3,5‐positions, were used in association with [Rh(μ‐Cl)(COD)]2 or [Rh(COD)2]PF6 in the reduction of methyl cinnamate, 2‐cyclohexen‐1‐one, cinnamaldehyde, and methyl α‐acetamidocinnamate in a two‐phase system D‐100/ethanol under 1 bar hydrogen at room temperature. Some differences in catalytic activity were observed in the reduction of methyl cinnamate, the most active catalyst being the rhodium complex containing the phosphane with the p‐fluorous ponytail. Recycling of the fluorous catalyst was possible, particularly using the p‐substituted phosphane, where no significant loss of catalyst or activity was observed, and generally with very low leaching of rhodium or phosphane in the organic phase.</description><subject>biphasic catalysis</subject><subject>catalyst recycling</subject><subject>fluorous</subject><subject>hydrogenation</subject><subject>iridium</subject><subject>rhodium</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNqFkM9PwjAcxRujiYhePfeoh0HbbS074nBggj8iJB6bsrZS2dalhcD86x1CiDdP35d83-cl7wFwi1EPI0T6Qvq8R1qFCCbkDHQwxXEQYZqcn3SMLsGV918IYTZgrAO270srzaYMUrEWRfOtJJw00tlPVYm1sRW0Gg6LlaqUh4sGHt39uTP-Thcb66woVnbX3NdL6-ulqBRMbVkXatcCpoLZr2fj4YNpv97kcNb4tSqvwYUWhVc3x9sF8-xxnk6C6ev4KR1OgzxMMAkiwSSOc9w2kpTGImaKKDnIYxwOGNEKRQixSMkFojphmslIJJjqEGtC5IKGXdA7xObOeu-U5rUzpXANx4jvV-P71fhptRZIDsDWFKr5x82Ho1n6lw0OrGkb7k6scCtOWchi_vEy5m_oOcvoKOQ4_AEkA4KA</recordid><startdate>200305</startdate><enddate>200305</enddate><creator>Sinou, Denis</creator><creator>Maillard, David</creator><creator>Aghmiz, Ali</creator><creator>Masdeu i-Bultó, Anna M.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200305</creationdate><title>Rhodium-Catalyzed Hydrogenation of Alkenes by Rhodium/Tris(fluoroalkoxy)phosphane Complexes in Fluorous Biphasic System</title><author>Sinou, Denis ; Maillard, David ; Aghmiz, Ali ; Masdeu i-Bultó, Anna M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3912-4a7d15c1212d665a57e2ed8c513872fe040074edb06f97f7d4a916f31f22db63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>biphasic catalysis</topic><topic>catalyst recycling</topic><topic>fluorous</topic><topic>hydrogenation</topic><topic>iridium</topic><topic>rhodium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sinou, Denis</creatorcontrib><creatorcontrib>Maillard, David</creatorcontrib><creatorcontrib>Aghmiz, Ali</creatorcontrib><creatorcontrib>Masdeu i-Bultó, Anna M.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sinou, Denis</au><au>Maillard, David</au><au>Aghmiz, Ali</au><au>Masdeu i-Bultó, Anna M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhodium-Catalyzed Hydrogenation of Alkenes by Rhodium/Tris(fluoroalkoxy)phosphane Complexes in Fluorous Biphasic System</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2003-05</date><risdate>2003</risdate><volume>345</volume><issue>5</issue><spage>603</spage><epage>611</epage><pages>603-611</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The reaction of [Ir(μ‐Cl)(COD)]2 with various fluorous derivatives of triphenylphosphane containing a para‐, meta‐, or ortho‐(1H,1H‐perfluoroalkoxy)‐substituted fluorous phosphane P(C6H4‐ORf)3 (Rf=CH2C7F15, CH2CH2CH2C8F17) and CO (1 atm) gives the corresponding trans‐[Ir(μ‐Cl)(CO){P(C6H4ORf)3}2]. The IR νCO values of these complexes give some information on the donor/acceptor properties of the phosphanes. These fluorous derivatives of triphenylphosphane, as well as a phosphane bearing two (1H,1H‐perfluoroalkyloxy) chains at the 3,5‐positions, were used in association with [Rh(μ‐Cl)(COD)]2 or [Rh(COD)2]PF6 in the reduction of methyl cinnamate, 2‐cyclohexen‐1‐one, cinnamaldehyde, and methyl α‐acetamidocinnamate in a two‐phase system D‐100/ethanol under 1 bar hydrogen at room temperature. Some differences in catalytic activity were observed in the reduction of methyl cinnamate, the most active catalyst being the rhodium complex containing the phosphane with the p‐fluorous ponytail. Recycling of the fluorous catalyst was possible, particularly using the p‐substituted phosphane, where no significant loss of catalyst or activity was observed, and generally with very low leaching of rhodium or phosphane in the organic phase.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.200202122</doi><tpages>9</tpages></addata></record> |
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subjects | biphasic catalysis catalyst recycling fluorous hydrogenation iridium rhodium |
title | Rhodium-Catalyzed Hydrogenation of Alkenes by Rhodium/Tris(fluoroalkoxy)phosphane Complexes in Fluorous Biphasic System |
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