Activation of Carbon Dioxide by Silyl Triflate-Based Frustrated Lewis Pairs
Silyl triflates of the form R4−nSi(OTf)n (n=1, 2; OTf=OSO3CF3) are shown to activate carbon dioxide when paired with bulky alkyl‐substituted Group 15 bases. Combinations of silyl triflates and 2,2,6,6‐tetramethylpiperidine react with CO2 to afford silyl carbamates via a frustrated Lewis pair‐type me...
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| Veröffentlicht in: | Chemistry : a European journal 2015-09, Vol.21 (37), p.13027-13034 |
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| container_title | Chemistry : a European journal |
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| creator | Weicker, Sarah A. Stephan, Douglas W. |
| description | Silyl triflates of the form R4−nSi(OTf)n (n=1, 2; OTf=OSO3CF3) are shown to activate carbon dioxide when paired with bulky alkyl‐substituted Group 15 bases. Combinations of silyl triflates and 2,2,6,6‐tetramethylpiperidine react with CO2 to afford silyl carbamates via a frustrated Lewis pair‐type mechanism. With trialkylphosphines, the silyl triflates R3Si(OTf) reversibly bind CO2 affording [R′3P(CO2)SiR3][OTf] whereas when Ph2Si(OTf)2 is used one or two molecules of CO2 can be sequestered. The latter bis‐CO2 product is favoured at low temperatures and by excess phosphine.
Silyl triflates of the form R4−nSi(OTf)n (n=1, 2; OTf=OSO3CF3) were shown to activate carbon dioxide when paired with bulky alkyl‐substituted Group 15 bases. Combinations of silyl triflates and 2,2,6,6‐tetramethylpiperidine react with CO2 to afford silyl carbamates via a frustrated Lewis pair‐type mechanism. |
| doi_str_mv | 10.1002/chem.201501904 |
| format | Article |
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Silyl triflates of the form R4−nSi(OTf)n (n=1, 2; OTf=OSO3CF3) were shown to activate carbon dioxide when paired with bulky alkyl‐substituted Group 15 bases. Combinations of silyl triflates and 2,2,6,6‐tetramethylpiperidine react with CO2 to afford silyl carbamates via a frustrated Lewis pair‐type mechanism.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201501904</identifier><identifier>PMID: 26223404</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activation ; Carbon capture and storage ; Carbon dioxide ; carbon dioxide activation ; Chemistry ; frustrated Lewis pairs ; Phosphines ; silicon ; silyl triflates</subject><ispartof>Chemistry : a European journal, 2015-09, Vol.21 (37), p.13027-13034</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><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-c6174-80849a6f356a7cfe0c96e4ed1bba43d96e0aa0c507ff1d57c1b386ce26e6b963</citedby><cites>FETCH-LOGICAL-c6174-80849a6f356a7cfe0c96e4ed1bba43d96e0aa0c507ff1d57c1b386ce26e6b963</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%2Fchem.201501904$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201501904$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26223404$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Weicker, Sarah A.</creatorcontrib><creatorcontrib>Stephan, Douglas W.</creatorcontrib><title>Activation of Carbon Dioxide by Silyl Triflate-Based Frustrated Lewis Pairs</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Silyl triflates of the form R4−nSi(OTf)n (n=1, 2; OTf=OSO3CF3) are shown to activate carbon dioxide when paired with bulky alkyl‐substituted Group 15 bases. Combinations of silyl triflates and 2,2,6,6‐tetramethylpiperidine react with CO2 to afford silyl carbamates via a frustrated Lewis pair‐type mechanism. With trialkylphosphines, the silyl triflates R3Si(OTf) reversibly bind CO2 affording [R′3P(CO2)SiR3][OTf] whereas when Ph2Si(OTf)2 is used one or two molecules of CO2 can be sequestered. The latter bis‐CO2 product is favoured at low temperatures and by excess phosphine.
Silyl triflates of the form R4−nSi(OTf)n (n=1, 2; OTf=OSO3CF3) were shown to activate carbon dioxide when paired with bulky alkyl‐substituted Group 15 bases. Combinations of silyl triflates and 2,2,6,6‐tetramethylpiperidine react with CO2 to afford silyl carbamates via a frustrated Lewis pair‐type mechanism.</description><subject>Activation</subject><subject>Carbon capture and storage</subject><subject>Carbon dioxide</subject><subject>carbon dioxide activation</subject><subject>Chemistry</subject><subject>frustrated Lewis pairs</subject><subject>Phosphines</subject><subject>silicon</subject><subject>silyl triflates</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkc1PGzEQxa2qqATaa4_VSr1w2TD-WHt9hADhI22pGqlHy-udVQ2bLNi7QP57HIVGiAunmZF-72meHiFfKYwpADt0_3AxZkALoBrEBzKiBaM5V7L4SEaghcplwfUu2YvxBgC05PwT2WWSMS5AjMjVkev9g-19t8y6JpvYUKXtxHdPvsasWmV_fLtqs3nwTWt7zI9txDo7C0PsQ7rrbIaPPmbX1of4mew0to345WXuk_nZ6Xxyns9-TS8mR7PcSapEXkIptJUNL6RVrkFwWqLAmlaVFbxOB1gLrgDVNLQulKMVL6VDJlFWKcA-OdjY3oXufsDYm4WPDtvWLrEboqElgNClTsHfRRWUVArB1uj3N-hNN4RlypEoKZVWXLFEjTeUC12MARtzF_zChpWhYNaFmHUhZltIEnx7sR2qBdZb_H8DCdAb4NG3uHrHzkzOT3-8Ns83Wh97fNpqbbg1Mr1bmL8_p-aSA7_-PRWG8me8iKR0</recordid><startdate>20150907</startdate><enddate>20150907</enddate><creator>Weicker, Sarah A.</creator><creator>Stephan, Douglas W.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20150907</creationdate><title>Activation of Carbon Dioxide by Silyl Triflate-Based Frustrated Lewis Pairs</title><author>Weicker, Sarah A. ; Stephan, Douglas W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6174-80849a6f356a7cfe0c96e4ed1bba43d96e0aa0c507ff1d57c1b386ce26e6b963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Activation</topic><topic>Carbon capture and storage</topic><topic>Carbon dioxide</topic><topic>carbon dioxide activation</topic><topic>Chemistry</topic><topic>frustrated Lewis pairs</topic><topic>Phosphines</topic><topic>silicon</topic><topic>silyl triflates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Weicker, Sarah A.</creatorcontrib><creatorcontrib>Stephan, Douglas W.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Weicker, Sarah A.</au><au>Stephan, Douglas W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Activation of Carbon Dioxide by Silyl Triflate-Based Frustrated Lewis Pairs</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2015-09-07</date><risdate>2015</risdate><volume>21</volume><issue>37</issue><spage>13027</spage><epage>13034</epage><pages>13027-13034</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Silyl triflates of the form R4−nSi(OTf)n (n=1, 2; OTf=OSO3CF3) are shown to activate carbon dioxide when paired with bulky alkyl‐substituted Group 15 bases. Combinations of silyl triflates and 2,2,6,6‐tetramethylpiperidine react with CO2 to afford silyl carbamates via a frustrated Lewis pair‐type mechanism. With trialkylphosphines, the silyl triflates R3Si(OTf) reversibly bind CO2 affording [R′3P(CO2)SiR3][OTf] whereas when Ph2Si(OTf)2 is used one or two molecules of CO2 can be sequestered. The latter bis‐CO2 product is favoured at low temperatures and by excess phosphine.
Silyl triflates of the form R4−nSi(OTf)n (n=1, 2; OTf=OSO3CF3) were shown to activate carbon dioxide when paired with bulky alkyl‐substituted Group 15 bases. Combinations of silyl triflates and 2,2,6,6‐tetramethylpiperidine react with CO2 to afford silyl carbamates via a frustrated Lewis pair‐type mechanism.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26223404</pmid><doi>10.1002/chem.201501904</doi><tpages>8</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Activation Carbon capture and storage Carbon dioxide carbon dioxide activation Chemistry frustrated Lewis pairs Phosphines silicon silyl triflates |
| title | Activation of Carbon Dioxide by Silyl Triflate-Based Frustrated Lewis Pairs |
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