Cooperative NHC and Photoredox Catalysis for the Synthesis of β‐Trifluoromethylated Alkyl Aryl Ketones
Despite the great potential of radical chemistry in organic synthesis, N‐heterocyclic carbene (NHC)‐catalyzed reactions involving radical intermediates are not well explored. This communication reports the three‐component coupling of aroyl fluorides, styrenes and the Langlois reagent (CF3SO2Na) to g...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2020-11, Vol.59 (45), p.19956-19960 |
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| creator | Meng, Qing‐Yuan Döben, Nadine Studer, Armido |
| description | Despite the great potential of radical chemistry in organic synthesis, N‐heterocyclic carbene (NHC)‐catalyzed reactions involving radical intermediates are not well explored. This communication reports the three‐component coupling of aroyl fluorides, styrenes and the Langlois reagent (CF3SO2Na) to give various β‐trifluoromethylated alkyl aryl ketones with good functional group tolerance in moderate to high yields by cooperative photoredox/NHC catalysis. The alkene acyltrifluoromethylation proceeds via radical/radical cross coupling of ketyl radicals with benzylic C‐radicals. The ketyl radicals are generated via SET reduction of in situ formed acylazolium ions whereas the benzylic radicals derive from trifluoromethyl radical addition onto styrenes.
Photoredox and NHC catalysis in concert: A novel strategy for the preparation of β‐trifluoromethylketones via radical alkene acyltrifluoromethylation has been developed. The three‐component cascades proceed under mild conditions with readily available aroyl fluorides, styrenes and the Langlois reagent as the reaction partners. |
| doi_str_mv | 10.1002/anie.202008040 |
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Photoredox and NHC catalysis in concert: A novel strategy for the preparation of β‐trifluoromethylketones via radical alkene acyltrifluoromethylation has been developed. The three‐component cascades proceed under mild conditions with readily available aroyl fluorides, styrenes and the Langlois reagent as the reaction partners.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202008040</identifier><identifier>PMID: 32700458</identifier><language>eng</language><publisher>WEINHEIM: Wiley</publisher><subject>Aromatic compounds ; Catalysis ; Chemical reactions ; Chemical synthesis ; Chemistry ; Chemistry, Multidisciplinary ; Communication ; Communications ; Cross coupling ; Fluorides ; Functional groups ; Intermediates ; Ketones ; NHC catalysis ; Photoredox catalysis ; Physical Sciences ; Radicals ; Reagents ; Science & Technology ; Styrenes ; trifluoromethylation ; visible light catalysis</subject><ispartof>Angewandte Chemie International Edition, 2020-11, Vol.59 (45), p.19956-19960</ispartof><rights>2020 The Authors. Published by Wiley-VCH GmbH</rights><rights>2020. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>163</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000564412800001</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c4450-b916c9fc81bd3e25c23ab3bf21b6dd8a21d708b3f7789d4345563d554a3852cd3</citedby><cites>FETCH-LOGICAL-c4450-b916c9fc81bd3e25c23ab3bf21b6dd8a21d708b3f7789d4345563d554a3852cd3</cites><orcidid>0000-0002-1706-513X</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.202008040$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202008040$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,315,782,786,887,1419,27933,27934,28257,45583,45584</link.rule.ids></links><search><creatorcontrib>Meng, Qing‐Yuan</creatorcontrib><creatorcontrib>Döben, Nadine</creatorcontrib><creatorcontrib>Studer, Armido</creatorcontrib><title>Cooperative NHC and Photoredox Catalysis for the Synthesis of β‐Trifluoromethylated Alkyl Aryl Ketones</title><title>Angewandte Chemie International Edition</title><addtitle>ANGEW CHEM INT EDIT</addtitle><description>Despite the great potential of radical chemistry in organic synthesis, N‐heterocyclic carbene (NHC)‐catalyzed reactions involving radical intermediates are not well explored. This communication reports the three‐component coupling of aroyl fluorides, styrenes and the Langlois reagent (CF3SO2Na) to give various β‐trifluoromethylated alkyl aryl ketones with good functional group tolerance in moderate to high yields by cooperative photoredox/NHC catalysis. The alkene acyltrifluoromethylation proceeds via radical/radical cross coupling of ketyl radicals with benzylic C‐radicals. The ketyl radicals are generated via SET reduction of in situ formed acylazolium ions whereas the benzylic radicals derive from trifluoromethyl radical addition onto styrenes.
Photoredox and NHC catalysis in concert: A novel strategy for the preparation of β‐trifluoromethylketones via radical alkene acyltrifluoromethylation has been developed. The three‐component cascades proceed under mild conditions with readily available aroyl fluorides, styrenes and the Langlois reagent as the reaction partners.</description><subject>Aromatic compounds</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry, Multidisciplinary</subject><subject>Communication</subject><subject>Communications</subject><subject>Cross coupling</subject><subject>Fluorides</subject><subject>Functional groups</subject><subject>Intermediates</subject><subject>Ketones</subject><subject>NHC catalysis</subject><subject>Photoredox catalysis</subject><subject>Physical Sciences</subject><subject>Radicals</subject><subject>Reagents</subject><subject>Science & Technology</subject><subject>Styrenes</subject><subject>trifluoromethylation</subject><subject>visible light catalysis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><sourceid>AOWDO</sourceid><recordid>eNqNkc2KFDEUhQtRnB_dug64EaTa_FalNkJTjDODwyg4rkOqcsvOWJ20SWq0dj6Cz-KD-BA-iWm6adGNbnIvyXcOJ5yieELwgmBMX2hnYUExxVhiju8Vx0RQUrK6ZvfzzhkraynIUXES423mpcTVw-KI0RpjLuRxYVvvNxB0sneAri9apJ1Bb1c--QDGf0GtTnqco41o8AGlFaB3s8tje-MH9OP7z6_fboIdxskHv4a0mkedwKDl-HEe0TLk4zUk7yA-Kh4MeozweD9Pi_evzm7ai_Lqzfllu7wqe84FLruGVH0z9JJ0hgEVPWW6Y91ASVcZIzUlpsayY0Ndy8ZwxoWomBGCayYF7Q07LV7ufDdTtwbTg0tBj2oT7FqHWXlt1Z8vzq7UB3-n6qphmDXZ4NneIPhPE8Sk1jb2MI7agZ-iopxWggkhWUaf_oXe-im4_L1MCY4bXlc8U4sd1QcfY4DhEIZgtW1RbVtUhxaz4PlO8Bk6P8TeguvhIMIYi4pzQmXeMMm0_H-6tSl37V3rJ5eytNlL7QjzP2Kp5fXl2e-QvwDnUcL9</recordid><startdate>20201102</startdate><enddate>20201102</enddate><creator>Meng, Qing‐Yuan</creator><creator>Döben, Nadine</creator><creator>Studer, Armido</creator><general>Wiley</general><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</scope><scope>1KM</scope><scope>AOWDO</scope><scope>BLEPL</scope><scope>DTL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-1706-513X</orcidid></search><sort><creationdate>20201102</creationdate><title>Cooperative NHC and Photoredox Catalysis for the Synthesis of β‐Trifluoromethylated Alkyl Aryl Ketones</title><author>Meng, Qing‐Yuan ; Döben, Nadine ; Studer, Armido</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4450-b916c9fc81bd3e25c23ab3bf21b6dd8a21d708b3f7789d4345563d554a3852cd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aromatic compounds</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry, Multidisciplinary</topic><topic>Communication</topic><topic>Communications</topic><topic>Cross coupling</topic><topic>Fluorides</topic><topic>Functional groups</topic><topic>Intermediates</topic><topic>Ketones</topic><topic>NHC catalysis</topic><topic>Photoredox catalysis</topic><topic>Physical Sciences</topic><topic>Radicals</topic><topic>Reagents</topic><topic>Science & Technology</topic><topic>Styrenes</topic><topic>trifluoromethylation</topic><topic>visible light catalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Meng, Qing‐Yuan</creatorcontrib><creatorcontrib>Döben, Nadine</creatorcontrib><creatorcontrib>Studer, Armido</creatorcontrib><collection>Wiley Online Library (Open Access Collection)</collection><collection>Wiley Free Content</collection><collection>Index Chemicus</collection><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Meng, Qing‐Yuan</au><au>Döben, Nadine</au><au>Studer, Armido</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cooperative NHC and Photoredox Catalysis for the Synthesis of β‐Trifluoromethylated Alkyl Aryl Ketones</atitle><jtitle>Angewandte Chemie International Edition</jtitle><stitle>ANGEW CHEM INT EDIT</stitle><date>2020-11-02</date><risdate>2020</risdate><volume>59</volume><issue>45</issue><spage>19956</spage><epage>19960</epage><pages>19956-19960</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Despite the great potential of radical chemistry in organic synthesis, N‐heterocyclic carbene (NHC)‐catalyzed reactions involving radical intermediates are not well explored. This communication reports the three‐component coupling of aroyl fluorides, styrenes and the Langlois reagent (CF3SO2Na) to give various β‐trifluoromethylated alkyl aryl ketones with good functional group tolerance in moderate to high yields by cooperative photoredox/NHC catalysis. The alkene acyltrifluoromethylation proceeds via radical/radical cross coupling of ketyl radicals with benzylic C‐radicals. The ketyl radicals are generated via SET reduction of in situ formed acylazolium ions whereas the benzylic radicals derive from trifluoromethyl radical addition onto styrenes.
Photoredox and NHC catalysis in concert: A novel strategy for the preparation of β‐trifluoromethylketones via radical alkene acyltrifluoromethylation has been developed. The three‐component cascades proceed under mild conditions with readily available aroyl fluorides, styrenes and the Langlois reagent as the reaction partners.</abstract><cop>WEINHEIM</cop><pub>Wiley</pub><pmid>32700458</pmid><doi>10.1002/anie.202008040</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-1706-513X</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Aromatic compounds Catalysis Chemical reactions Chemical synthesis Chemistry Chemistry, Multidisciplinary Communication Communications Cross coupling Fluorides Functional groups Intermediates Ketones NHC catalysis Photoredox catalysis Physical Sciences Radicals Reagents Science & Technology Styrenes trifluoromethylation visible light catalysis |
| title | Cooperative NHC and Photoredox Catalysis for the Synthesis of β‐Trifluoromethylated Alkyl Aryl Ketones |
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