Synthesis of Multifluoromethylated γ‐Sultines by a Photoinduced Radical Addition–Polar Cyclization
Despite the significance of sultines in synthesis, medicine, and materials science, the chemistry of sultines has remained unexplored due to their inaccessibility. Herein, we demonstrate the development of a photoredox‐catalyzed multifluoromethyl radical addition/SO2 incorporation/polar cyclization...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2023-04, Vol.62 (15), p.e202300159-n/a |
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| creator | Li, Helian Zhang, Yongxin Yang, Xiaoxiao Deng, Zhenxi Zhu, Zhimin Zhou, Pan Ouyang, Xinke Yuan, Yuting Chen, Xi Yang, Lingyue Liu, Meng Shu, Chao |
| description | Despite the significance of sultines in synthesis, medicine, and materials science, the chemistry of sultines has remained unexplored due to their inaccessibility. Herein, we demonstrate the development of a photoredox‐catalyzed multifluoromethyl radical addition/SO2 incorporation/polar cyclization cascade approach to multifluoromethylated γ‐sultines. The reactions proceed by single electron transfer induced multifluoromethyl radical addition to an alkene followed by SO2 incorporation, and single‐electron reduction for polar 5‐exo‐tet cyclization. Key to the success of the protocol is the use of easily oxidizable multifluoroalkanesulfinates as bifunctional reagents. The reactions proceed with excellent functional‐group tolerance to deliver γ‐sultines in moderate to excellent yields.
A photoredox‐catalyzed multifluoromethyl radical addition/SO2 incorporation/polar cyclization cascade approach to multifluoromethylated γ‐sultines has been developed. The reaction proceeds with broad functional‐group tolerance and good yields. Key to the success of the protocol is use of oxidizable multifluoroalkanesulfinates as bifunctional reagents. |
| doi_str_mv | 10.1002/anie.202300159 |
| format | Article |
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A photoredox‐catalyzed multifluoromethyl radical addition/SO2 incorporation/polar cyclization cascade approach to multifluoromethylated γ‐sultines has been developed. The reaction proceeds with broad functional‐group tolerance and good yields. Key to the success of the protocol is use of oxidizable multifluoroalkanesulfinates as bifunctional reagents.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202300159</identifier><identifier>PMID: 36762878</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Chemical synthesis ; Electron transfer ; Fluorination ; Materials science ; Photoredox Catalysis ; Radicals ; Reagents ; Single electrons ; Sulfur ; Sulfur dioxide ; γ-Sultines</subject><ispartof>Angewandte Chemie International Edition, 2023-04, Vol.62 (15), p.e202300159-n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2023 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3739-25cd271884030f636f93e440d49abecd72ee4b4a8888b6472cbf01b4090bd273</citedby><cites>FETCH-LOGICAL-c3739-25cd271884030f636f93e440d49abecd72ee4b4a8888b6472cbf01b4090bd273</cites><orcidid>0000-0002-4722-2714</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.202300159$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202300159$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36762878$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Helian</creatorcontrib><creatorcontrib>Zhang, Yongxin</creatorcontrib><creatorcontrib>Yang, Xiaoxiao</creatorcontrib><creatorcontrib>Deng, Zhenxi</creatorcontrib><creatorcontrib>Zhu, Zhimin</creatorcontrib><creatorcontrib>Zhou, Pan</creatorcontrib><creatorcontrib>Ouyang, Xinke</creatorcontrib><creatorcontrib>Yuan, Yuting</creatorcontrib><creatorcontrib>Chen, Xi</creatorcontrib><creatorcontrib>Yang, Lingyue</creatorcontrib><creatorcontrib>Liu, Meng</creatorcontrib><creatorcontrib>Shu, Chao</creatorcontrib><title>Synthesis of Multifluoromethylated γ‐Sultines by a Photoinduced Radical Addition–Polar Cyclization</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Despite the significance of sultines in synthesis, medicine, and materials science, the chemistry of sultines has remained unexplored due to their inaccessibility. Herein, we demonstrate the development of a photoredox‐catalyzed multifluoromethyl radical addition/SO2 incorporation/polar cyclization cascade approach to multifluoromethylated γ‐sultines. The reactions proceed by single electron transfer induced multifluoromethyl radical addition to an alkene followed by SO2 incorporation, and single‐electron reduction for polar 5‐exo‐tet cyclization. Key to the success of the protocol is the use of easily oxidizable multifluoroalkanesulfinates as bifunctional reagents. The reactions proceed with excellent functional‐group tolerance to deliver γ‐sultines in moderate to excellent yields.
A photoredox‐catalyzed multifluoromethyl radical addition/SO2 incorporation/polar cyclization cascade approach to multifluoromethylated γ‐sultines has been developed. The reaction proceeds with broad functional‐group tolerance and good yields. Key to the success of the protocol is use of oxidizable multifluoroalkanesulfinates as bifunctional reagents.</description><subject>Chemical synthesis</subject><subject>Electron transfer</subject><subject>Fluorination</subject><subject>Materials science</subject><subject>Photoredox Catalysis</subject><subject>Radicals</subject><subject>Reagents</subject><subject>Single electrons</subject><subject>Sulfur</subject><subject>Sulfur dioxide</subject><subject>γ-Sultines</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkclKBDEQhoMo7leP0uDFS4_ZOkkfh2FcYFxQ7006STuRTEc73Uh78hEEH8X38CHmScwwLuDFulRR9dVPUT8AewgOEIT4SNbWDDDEBEKU5StgE2UYpYRzshprSkjKRYY2wFYI95EXArJ1sEEYZ1hwsQnubvq6nZpgQ-Kr5Lxzra1c5xs_M-20d7I1Ovl4n7-83ixGtQlJ2ScyuZr61ttadyrOr6W2SrpkqLVtra_nL29X3skmGfXK2We56O2AtUq6YHa_8ja4PR7fjk7TyeXJ2Wg4SRXhJE9xpjTmSAgKCawYYVVODKVQ01yWRmmOjaEllSJGySjHqqwgKinMYRkXyTY4XMo-NP6xM6EtZjYo45ysje9CgTnPGCZMoIge_EHvfdfU8bhI5QjyLOMsUoMlpRofQmOq4qGxM9n0BYLFwoFi4UDx40Bc2P-S7cqZ0T_498sjkC-BJ-tM_49cMbw4G_-KfwINQ5WQ</recordid><startdate>20230403</startdate><enddate>20230403</enddate><creator>Li, Helian</creator><creator>Zhang, Yongxin</creator><creator>Yang, Xiaoxiao</creator><creator>Deng, Zhenxi</creator><creator>Zhu, Zhimin</creator><creator>Zhou, Pan</creator><creator>Ouyang, Xinke</creator><creator>Yuan, Yuting</creator><creator>Chen, Xi</creator><creator>Yang, Lingyue</creator><creator>Liu, Meng</creator><creator>Shu, Chao</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-4722-2714</orcidid></search><sort><creationdate>20230403</creationdate><title>Synthesis of Multifluoromethylated γ‐Sultines by a Photoinduced Radical Addition–Polar Cyclization</title><author>Li, Helian ; Zhang, Yongxin ; Yang, Xiaoxiao ; Deng, Zhenxi ; Zhu, Zhimin ; Zhou, Pan ; Ouyang, Xinke ; Yuan, Yuting ; Chen, Xi ; Yang, Lingyue ; Liu, Meng ; Shu, Chao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3739-25cd271884030f636f93e440d49abecd72ee4b4a8888b6472cbf01b4090bd273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Chemical synthesis</topic><topic>Electron transfer</topic><topic>Fluorination</topic><topic>Materials science</topic><topic>Photoredox Catalysis</topic><topic>Radicals</topic><topic>Reagents</topic><topic>Single electrons</topic><topic>Sulfur</topic><topic>Sulfur dioxide</topic><topic>γ-Sultines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Helian</creatorcontrib><creatorcontrib>Zhang, Yongxin</creatorcontrib><creatorcontrib>Yang, Xiaoxiao</creatorcontrib><creatorcontrib>Deng, Zhenxi</creatorcontrib><creatorcontrib>Zhu, Zhimin</creatorcontrib><creatorcontrib>Zhou, Pan</creatorcontrib><creatorcontrib>Ouyang, Xinke</creatorcontrib><creatorcontrib>Yuan, Yuting</creatorcontrib><creatorcontrib>Chen, Xi</creatorcontrib><creatorcontrib>Yang, Lingyue</creatorcontrib><creatorcontrib>Liu, Meng</creatorcontrib><creatorcontrib>Shu, Chao</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Helian</au><au>Zhang, Yongxin</au><au>Yang, Xiaoxiao</au><au>Deng, Zhenxi</au><au>Zhu, Zhimin</au><au>Zhou, Pan</au><au>Ouyang, Xinke</au><au>Yuan, Yuting</au><au>Chen, Xi</au><au>Yang, Lingyue</au><au>Liu, Meng</au><au>Shu, Chao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Multifluoromethylated γ‐Sultines by a Photoinduced Radical Addition–Polar Cyclization</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2023-04-03</date><risdate>2023</risdate><volume>62</volume><issue>15</issue><spage>e202300159</spage><epage>n/a</epage><pages>e202300159-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Despite the significance of sultines in synthesis, medicine, and materials science, the chemistry of sultines has remained unexplored due to their inaccessibility. Herein, we demonstrate the development of a photoredox‐catalyzed multifluoromethyl radical addition/SO2 incorporation/polar cyclization cascade approach to multifluoromethylated γ‐sultines. The reactions proceed by single electron transfer induced multifluoromethyl radical addition to an alkene followed by SO2 incorporation, and single‐electron reduction for polar 5‐exo‐tet cyclization. Key to the success of the protocol is the use of easily oxidizable multifluoroalkanesulfinates as bifunctional reagents. The reactions proceed with excellent functional‐group tolerance to deliver γ‐sultines in moderate to excellent yields.
A photoredox‐catalyzed multifluoromethyl radical addition/SO2 incorporation/polar cyclization cascade approach to multifluoromethylated γ‐sultines has been developed. The reaction proceeds with broad functional‐group tolerance and good yields. Key to the success of the protocol is use of oxidizable multifluoroalkanesulfinates as bifunctional reagents.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36762878</pmid><doi>10.1002/anie.202300159</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-4722-2714</orcidid></addata></record> |
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| subjects | Chemical synthesis Electron transfer Fluorination Materials science Photoredox Catalysis Radicals Reagents Single electrons Sulfur Sulfur dioxide γ-Sultines |
| title | Synthesis of Multifluoromethylated γ‐Sultines by a Photoinduced Radical Addition–Polar Cyclization |
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