Accessing SuFExable Cyclobutane‐Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles
Indoline‐fused polycycles are commonly found as a key structural component in numerous natural products and biologically active compounds. In recent times, the incorporation of sulfonyl fluoride groups has drawn significant attention in research due to their potential to enhance or confer new biolog...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2024-07, Vol.366 (14), p.3117-3122 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Wei, Rongbiao Pei, Guanhua Huang, Yao Liao, Saihu |
| description | Indoline‐fused polycycles are commonly found as a key structural component in numerous natural products and biologically active compounds. In recent times, the incorporation of sulfonyl fluoride groups has drawn significant attention in research due to their potential to enhance or confer new biological activities to molecules. In this study, we report the development of a modular approach for synthesizing FSO2‐functionalized cyclobutane‐fused indolines by employing an intermolecular [2+2] cycloaddition reaction between indoles and SuFExable ethenesulfonyl fluoride under triplet energy‐transfer catalysis. This method features mild reaction conditions, metal‐free photocatalysts, and excellent tolerance to various functional groups. Moreover, we demonstrate the feasibility of further modifying the FSO2‐functionalized indoline products via SuFEx click reactions, enabling their conjugation with other molecules. |
| doi_str_mv | 10.1002/adsc.202400274 |
| format | Article |
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In recent times, the incorporation of sulfonyl fluoride groups has drawn significant attention in research due to their potential to enhance or confer new biological activities to molecules. In this study, we report the development of a modular approach for synthesizing FSO2‐functionalized cyclobutane‐fused indolines by employing an intermolecular [2+2] cycloaddition reaction between indoles and SuFExable ethenesulfonyl fluoride under triplet energy‐transfer catalysis. This method features mild reaction conditions, metal‐free photocatalysts, and excellent tolerance to various functional groups. 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Moreover, we demonstrate the feasibility of further modifying the FSO2‐functionalized indoline products via SuFEx click reactions, enabling their conjugation with other molecules.</description><subject>Chemical synthesis</subject><subject>Conjugation</subject><subject>Cycloaddition</subject><subject>Cyclobutane</subject><subject>Functional groups</subject><subject>Heterocyclic compounds</subject><subject>Indoles</subject><subject>Indolines</subject><subject>Intermolecular [2+2] cycloaddition</subject><subject>Natural products</subject><subject>Photocatalysis</subject><subject>SuFEx click reactions</subject><subject>Sulfonyl fluorides</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkMFKxDAQhoMouK5ePRc8StckbdP0uNRdXVhQUE8iIU1SzZJt1qRVe_MRfEafxCyV9ehpZpjv_4f5AThFcIIgxBdcejHBEKdhyNM9MEIEZXGKSLG_6zN4CI68X0GIcprnI-CmQijvdfMc3XXz2QevjIrKXhhbdS1v1Pfn17zzSkaLRlqjG-WjN82j2xfbWsFbbvpWi7BslVtbo0RnuIse8Tl-Gly4lLrVtolsPVgofwwOam68OvmtY_Awn92X1_Hy5mpRTpex2D4RY5EXCa5qLhWhkBapQIkShCQJqSqS1bySQkJJIakhlzXNKUdQpYKGmaacJGNwNvhunH3tlG_ZynauCSdZEgiSowyngZoMlHDWe6dqtnF6zV3PEGTbXNk2V7bLNQiKQfCujer_odn08q780_4AoCd-oA</recordid><startdate>20240716</startdate><enddate>20240716</enddate><creator>Wei, Rongbiao</creator><creator>Pei, Guanhua</creator><creator>Huang, Yao</creator><creator>Liao, Saihu</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-0251-8757</orcidid></search><sort><creationdate>20240716</creationdate><title>Accessing SuFExable Cyclobutane‐Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles</title><author>Wei, Rongbiao ; Pei, Guanhua ; Huang, Yao ; Liao, Saihu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2024-2c7932bfade680894c13ec66336bb65fabdcd0d806f0adf878a10e4c86f084a63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Chemical synthesis</topic><topic>Conjugation</topic><topic>Cycloaddition</topic><topic>Cyclobutane</topic><topic>Functional groups</topic><topic>Heterocyclic compounds</topic><topic>Indoles</topic><topic>Indolines</topic><topic>Intermolecular [2+2] cycloaddition</topic><topic>Natural products</topic><topic>Photocatalysis</topic><topic>SuFEx click reactions</topic><topic>Sulfonyl fluorides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wei, Rongbiao</creatorcontrib><creatorcontrib>Pei, Guanhua</creatorcontrib><creatorcontrib>Huang, Yao</creatorcontrib><creatorcontrib>Liao, Saihu</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wei, Rongbiao</au><au>Pei, Guanhua</au><au>Huang, Yao</au><au>Liao, Saihu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Accessing SuFExable Cyclobutane‐Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2024-07-16</date><risdate>2024</risdate><volume>366</volume><issue>14</issue><spage>3117</spage><epage>3122</epage><pages>3117-3122</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Indoline‐fused polycycles are commonly found as a key structural component in numerous natural products and biologically active compounds. 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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Chemical synthesis Conjugation Cycloaddition Cyclobutane Functional groups Heterocyclic compounds Indoles Indolines Intermolecular [2+2] cycloaddition Natural products Photocatalysis SuFEx click reactions Sulfonyl fluorides |
| title | Accessing SuFExable Cyclobutane‐Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles |
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