Perfluoroalkyl Selenoxides, Selenones and Selenoximines: General Preparation and Properties
A selective access to perfluoroalkyl selenoxides, via Oxone® as oxidant or to selenones by using a Polyoxometalate‐based Ionic Liquid (POM‐IL) as a catalyst for the oxidation step is described. The reaction works with various perfluoralkyl chains and substituents with satisfactory to excellent yield...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2023-03, Vol.62 (12), p.e202300951-n/a |
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| creator | Zordo‐Banliat, Arnaud Grollier, Kevin Vanthuyne, Nicolas Floquet, Sébastien Billard, Thierry Dagousset, Guillaume Pégot, Bruce Magnier, Emmanuel |
| description | A selective access to perfluoroalkyl selenoxides, via Oxone® as oxidant or to selenones by using a Polyoxometalate‐based Ionic Liquid (POM‐IL) as a catalyst for the oxidation step is described. The reaction works with various perfluoralkyl chains and substituents with satisfactory to excellent yields. A two‐step one‐pot reaction from selenocyanates was performed to gain access to perfluoroalkyl selenoxides. The previously unknown perfluoroalkyl selenoximines family was also prepared with good yields. Having unlocked two strategies for the synthesis of fluoroalkylated SeIV and SeVI compounds, we then evaluated the Hansch‐Leo lipophilicity parameters of these groups. Finally, asymmetric aryl perfluoroalkyl selenoximines were resolved to determine their absolute configurations.
Access to perfluoroalkyl selenoxides, selenones and selenoximines was possible through a selective oxidation of perfluoroalkyl selenoethers. Synthesis of perfluoroalkyl selenoxides was also described via a two‐step one‐pot reaction from selenocyanates. The perfluoroalkyl selenoximine family was synthesized. The Hansch‐Leo parameters of the compounds were determined and some aryl perfluoroalkyl selenoxides were separated by chiral HPLC. |
| doi_str_mv | 10.1002/anie.202300951 |
| format | Article |
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Access to perfluoroalkyl selenoxides, selenones and selenoximines was possible through a selective oxidation of perfluoroalkyl selenoethers. Synthesis of perfluoroalkyl selenoxides was also described via a two‐step one‐pot reaction from selenocyanates. The perfluoroalkyl selenoximine family was synthesized. The Hansch‐Leo parameters of the compounds were determined and some aryl perfluoroalkyl selenoxides were separated by chiral HPLC.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202300951</identifier><identifier>PMID: 36705091</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Catalysts ; Chemical Sciences ; Fluorine ; Ionic liquids ; Oxidants ; Oxidation ; Oxidizing agents ; Perfluoro compounds ; Perfluoroalkyl & polyfluoroalkyl substances ; Polyoxometallates ; Selenium ; Selenones ; Selenoxides ; Selenoximines</subject><ispartof>Angewandte Chemie International Edition, 2023-03, Vol.62 (12), p.e202300951-n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2023 Wiley-VCH GmbH.</rights><rights>2023. This article is published under http://creativecommons.org/licenses/by-nc-nd/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4471-c2f2ed1926e2ef34f383f6f3d2a8d84e4045985f4af25642c2b35e81703221353</citedby><cites>FETCH-LOGICAL-c4471-c2f2ed1926e2ef34f383f6f3d2a8d84e4045985f4af25642c2b35e81703221353</cites><orcidid>0000-0003-2598-7940 ; 0000-0001-5137-5548 ; 0000-0001-8720-3828 ; 0000-0002-2937-9523 ; 0000-0003-2433-1771 ; 0000-0003-3392-3971 ; 0000-0003-0850-8653</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.202300951$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202300951$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36705091$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-04046563$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Zordo‐Banliat, Arnaud</creatorcontrib><creatorcontrib>Grollier, Kevin</creatorcontrib><creatorcontrib>Vanthuyne, Nicolas</creatorcontrib><creatorcontrib>Floquet, Sébastien</creatorcontrib><creatorcontrib>Billard, Thierry</creatorcontrib><creatorcontrib>Dagousset, Guillaume</creatorcontrib><creatorcontrib>Pégot, Bruce</creatorcontrib><creatorcontrib>Magnier, Emmanuel</creatorcontrib><title>Perfluoroalkyl Selenoxides, Selenones and Selenoximines: General Preparation and Properties</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>A selective access to perfluoroalkyl selenoxides, via Oxone® as oxidant or to selenones by using a Polyoxometalate‐based Ionic Liquid (POM‐IL) as a catalyst for the oxidation step is described. The reaction works with various perfluoralkyl chains and substituents with satisfactory to excellent yields. A two‐step one‐pot reaction from selenocyanates was performed to gain access to perfluoroalkyl selenoxides. The previously unknown perfluoroalkyl selenoximines family was also prepared with good yields. Having unlocked two strategies for the synthesis of fluoroalkylated SeIV and SeVI compounds, we then evaluated the Hansch‐Leo lipophilicity parameters of these groups. Finally, asymmetric aryl perfluoroalkyl selenoximines were resolved to determine their absolute configurations.
Access to perfluoroalkyl selenoxides, selenones and selenoximines was possible through a selective oxidation of perfluoroalkyl selenoethers. Synthesis of perfluoroalkyl selenoxides was also described via a two‐step one‐pot reaction from selenocyanates. The perfluoroalkyl selenoximine family was synthesized. The Hansch‐Leo parameters of the compounds were determined and some aryl perfluoroalkyl selenoxides were separated by chiral HPLC.</description><subject>Catalysts</subject><subject>Chemical Sciences</subject><subject>Fluorine</subject><subject>Ionic liquids</subject><subject>Oxidants</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Perfluoro compounds</subject><subject>Perfluoroalkyl & polyfluoroalkyl substances</subject><subject>Polyoxometallates</subject><subject>Selenium</subject><subject>Selenones</subject><subject>Selenoxides</subject><subject>Selenoximines</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkUtLAzEURoMoPqpbl1Jwo-DUPGcy7or4KBQtqCsXIc7cYDSd1KSj9t-b2lrBjZs8bs49JPkQ2ie4RzCmp7qx0KOYMoxLQdbQNhGUZKwo2Hpac8ayQgqyhXZifEm8lDjfRFssL7DAJdlGjyMIxrU-eO1eZ657Bw4a_2lriCfLTQOxq5t6dTS2qXLWvYIGgnbdUYCJDnpqffONjYKfQJhaiLtow2gXYW85d9DD5cX9-XU2vL0anPeHWcV5QbKKGgo1KWkOFAzjhklmcsNqqmUtOXDMRSmF4dpQkXNa0ScmQJICM0oJE6yDjhfeZ-3UJNixDjPltVXX_aGa13BS5CJn7ySxRwt2EvxbC3GqxjZW4JxuwLdR0aLAhJRpSOjhH_TFt6FJL0mUTF_JxTfVW1BV8DEGMKsbEKzmEal5RGoVUWo4WGrbpzHUK_wnkwSUC-DDOpj9o1P9m8HFr_wL772bkw</recordid><startdate>20230313</startdate><enddate>20230313</enddate><creator>Zordo‐Banliat, Arnaud</creator><creator>Grollier, Kevin</creator><creator>Vanthuyne, Nicolas</creator><creator>Floquet, Sébastien</creator><creator>Billard, Thierry</creator><creator>Dagousset, Guillaume</creator><creator>Pégot, Bruce</creator><creator>Magnier, Emmanuel</creator><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-2598-7940</orcidid><orcidid>https://orcid.org/0000-0001-5137-5548</orcidid><orcidid>https://orcid.org/0000-0001-8720-3828</orcidid><orcidid>https://orcid.org/0000-0002-2937-9523</orcidid><orcidid>https://orcid.org/0000-0003-2433-1771</orcidid><orcidid>https://orcid.org/0000-0003-3392-3971</orcidid><orcidid>https://orcid.org/0000-0003-0850-8653</orcidid></search><sort><creationdate>20230313</creationdate><title>Perfluoroalkyl Selenoxides, Selenones and Selenoximines: General Preparation and Properties</title><author>Zordo‐Banliat, Arnaud ; 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Access to perfluoroalkyl selenoxides, selenones and selenoximines was possible through a selective oxidation of perfluoroalkyl selenoethers. Synthesis of perfluoroalkyl selenoxides was also described via a two‐step one‐pot reaction from selenocyanates. The perfluoroalkyl selenoximine family was synthesized. The Hansch‐Leo parameters of the compounds were determined and some aryl perfluoroalkyl selenoxides were separated by chiral HPLC.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36705091</pmid><doi>10.1002/anie.202300951</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-2598-7940</orcidid><orcidid>https://orcid.org/0000-0001-5137-5548</orcidid><orcidid>https://orcid.org/0000-0001-8720-3828</orcidid><orcidid>https://orcid.org/0000-0002-2937-9523</orcidid><orcidid>https://orcid.org/0000-0003-2433-1771</orcidid><orcidid>https://orcid.org/0000-0003-3392-3971</orcidid><orcidid>https://orcid.org/0000-0003-0850-8653</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Catalysts Chemical Sciences Fluorine Ionic liquids Oxidants Oxidation Oxidizing agents Perfluoro compounds Perfluoroalkyl & polyfluoroalkyl substances Polyoxometallates Selenium Selenones Selenoxides Selenoximines |
| title | Perfluoroalkyl Selenoxides, Selenones and Selenoximines: General Preparation and Properties |
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