Cu I ‐Catalyzed Pentafluoroethylation of Aryl Iodides in the Presence of Tetrafluoroethylene and Cesium Fluoride: Determining the Route to the Key Pentafluoroethyl Cu I Intermediate
The Cu(I)‐catalyzed pentafluoroethylation of iodoarenes via the fluorocupration of tetrafluoroethylene (TFE) is disclosed. The active species, (phen)CuC 2 F 5 , was isolated and its molecular structure confirmed by a single‐crystal X‐ray diffraction analysis. The key to the successful suppression of...
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| Veröffentlicht in: | Chemistry : a European journal 2018-07, Vol.24 (39), p.9794-9798 |
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| container_end_page | 9798 |
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| container_issue | 39 |
| container_start_page | 9794 |
| container_title | Chemistry : a European journal |
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| creator | Ohashi, Masato Ishida, Naoyoshi Ando, Kota Hashimoto, Yu Shigaki, Anna Kikushima, Kotaro Ogoshi, Sensuke |
| description | The Cu(I)‐catalyzed pentafluoroethylation of iodoarenes via the fluorocupration of tetrafluoroethylene (TFE) is disclosed. The active species, (phen)CuC
2
F
5
, was isolated and its molecular structure confirmed by a single‐crystal X‐ray diffraction analysis. The key to the successful suppression of the competing oligomerization of TFE is to refrain from stirring the reaction mixture. A mechanistic study clearly discarded the possibility that the catalytic reaction proceeds via a radical pathway. |
| doi_str_mv | 10.1002/chem.201802415 |
| format | Article |
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2
F
5
, was isolated and its molecular structure confirmed by a single‐crystal X‐ray diffraction analysis. The key to the successful suppression of the competing oligomerization of TFE is to refrain from stirring the reaction mixture. A mechanistic study clearly discarded the possibility that the catalytic reaction proceeds via a radical pathway.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201802415</identifier><language>eng</language><ispartof>Chemistry : a European journal, 2018-07, Vol.24 (39), p.9794-9798</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c169t-1e3387a4965182885d068d3a0c45175a8606629806edf2e6c2ab9903dee7f0a63</citedby><cites>FETCH-LOGICAL-c169t-1e3387a4965182885d068d3a0c45175a8606629806edf2e6c2ab9903dee7f0a63</cites><orcidid>0000-0001-8718-2799</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></links><search><creatorcontrib>Ohashi, Masato</creatorcontrib><creatorcontrib>Ishida, Naoyoshi</creatorcontrib><creatorcontrib>Ando, Kota</creatorcontrib><creatorcontrib>Hashimoto, Yu</creatorcontrib><creatorcontrib>Shigaki, Anna</creatorcontrib><creatorcontrib>Kikushima, Kotaro</creatorcontrib><creatorcontrib>Ogoshi, Sensuke</creatorcontrib><title>Cu I ‐Catalyzed Pentafluoroethylation of Aryl Iodides in the Presence of Tetrafluoroethylene and Cesium Fluoride: Determining the Route to the Key Pentafluoroethyl Cu I Intermediate</title><title>Chemistry : a European journal</title><description>The Cu(I)‐catalyzed pentafluoroethylation of iodoarenes via the fluorocupration of tetrafluoroethylene (TFE) is disclosed. The active species, (phen)CuC
2
F
5
, was isolated and its molecular structure confirmed by a single‐crystal X‐ray diffraction analysis. The key to the successful suppression of the competing oligomerization of TFE is to refrain from stirring the reaction mixture. A mechanistic study clearly discarded the possibility that the catalytic reaction proceeds via a radical pathway.</description><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNplkMFKxDAURYMoOI5uXecHOr40Tdq4G6qjxQEHGdclNq9OpZNKki7qyk_wb_wfv0Q7igiuHo_LuVwOIacMZgwgPqs2uJ3FwDKIEyb2yISJmEU8lWKfTEAlaSQFV4fkyPsnAFCS8wl5z3ta0I_Xt1wH3Q4vaOgKbdB123euw7AZWh2aztKupnM3tLToTGPQ08bSsEG6cujRVjjmawzuL4gWqbaG5uibfksXY_LFntMLDOi2jW3s467krusD0tDtnhsc_k2gu5WFHTE0jQ54TA5q3Xo8-blTcr-4XOfX0fL2qsjny6hiUoWIIedZqhMlBcviLBMGZGa4hioRLBU6kyBlrDKQaOoYZRXrB6WAG8S0Bi35lMy-eyvXee-wLp9ds9VuKBmUo_Zy1F7-auefhjt6bA</recordid><startdate>20180711</startdate><enddate>20180711</enddate><creator>Ohashi, Masato</creator><creator>Ishida, Naoyoshi</creator><creator>Ando, Kota</creator><creator>Hashimoto, Yu</creator><creator>Shigaki, Anna</creator><creator>Kikushima, Kotaro</creator><creator>Ogoshi, Sensuke</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8718-2799</orcidid></search><sort><creationdate>20180711</creationdate><title>Cu I ‐Catalyzed Pentafluoroethylation of Aryl Iodides in the Presence of Tetrafluoroethylene and Cesium Fluoride: Determining the Route to the Key Pentafluoroethyl Cu I Intermediate</title><author>Ohashi, Masato ; Ishida, Naoyoshi ; Ando, Kota ; Hashimoto, Yu ; Shigaki, Anna ; Kikushima, Kotaro ; Ogoshi, Sensuke</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c169t-1e3387a4965182885d068d3a0c45175a8606629806edf2e6c2ab9903dee7f0a63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ohashi, Masato</creatorcontrib><creatorcontrib>Ishida, Naoyoshi</creatorcontrib><creatorcontrib>Ando, Kota</creatorcontrib><creatorcontrib>Hashimoto, Yu</creatorcontrib><creatorcontrib>Shigaki, Anna</creatorcontrib><creatorcontrib>Kikushima, Kotaro</creatorcontrib><creatorcontrib>Ogoshi, Sensuke</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ohashi, Masato</au><au>Ishida, Naoyoshi</au><au>Ando, Kota</au><au>Hashimoto, Yu</au><au>Shigaki, Anna</au><au>Kikushima, Kotaro</au><au>Ogoshi, Sensuke</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cu I ‐Catalyzed Pentafluoroethylation of Aryl Iodides in the Presence of Tetrafluoroethylene and Cesium Fluoride: Determining the Route to the Key Pentafluoroethyl Cu I Intermediate</atitle><jtitle>Chemistry : a European journal</jtitle><date>2018-07-11</date><risdate>2018</risdate><volume>24</volume><issue>39</issue><spage>9794</spage><epage>9798</epage><pages>9794-9798</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>The Cu(I)‐catalyzed pentafluoroethylation of iodoarenes via the fluorocupration of tetrafluoroethylene (TFE) is disclosed. The active species, (phen)CuC
2
F
5
, was isolated and its molecular structure confirmed by a single‐crystal X‐ray diffraction analysis. The key to the successful suppression of the competing oligomerization of TFE is to refrain from stirring the reaction mixture. A mechanistic study clearly discarded the possibility that the catalytic reaction proceeds via a radical pathway.</abstract><doi>10.1002/chem.201802415</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-8718-2799</orcidid></addata></record> |
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| language | eng |
| recordid | cdi_crossref_primary_10_1002_chem_201802415 |
| source | Wiley Online Library Journals Frontfile Complete |
| title | Cu I ‐Catalyzed Pentafluoroethylation of Aryl Iodides in the Presence of Tetrafluoroethylene and Cesium Fluoride: Determining the Route to the Key Pentafluoroethyl Cu I Intermediate |
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