Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C–S bond cleavage
Developing new alkyl electrophiles for the construction of C sp 3 –C sp 2 bonds through a Heck-like coupling is a huge challenge and has attracted great interest in synthetic and medicinal chemistry. In this study, the first example of Heck-like coupling of cyclic sulfonium salts with alkenes via se...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2024-04, Vol.11 (8), p.2195-2200 |
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| container_issue | 8 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Liu, Xianqin Li, Xufeng Wang, Linyuan Shi, Yongjia Lv, Jian Yang, Daoshan |
| description | Developing new alkyl electrophiles for the construction of C
sp
3
–C
sp
2
bonds through a Heck-like coupling is a huge challenge and has attracted great interest in synthetic and medicinal chemistry. In this study, the first example of Heck-like coupling of cyclic sulfonium salts with alkenes
via
selective C–S bond cleavage using a copper complex as a photosensitizer through a visible-light-driven redox-neutral process is demonstrated. The C–S bond cleavage/Heck-like coupling reaction delivers a variety of corresponding internal alkenes containing aryl alkyl thioethers with good functional group tolerance. This strategy will further expand the new reaction modes of sulfonium salts and provide new insights into the construction of C
sp
3
–C
sp
2
bonds. |
| doi_str_mv | 10.1039/D3QO02009F |
| format | Article |
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sp
3
–C
sp
2
bonds through a Heck-like coupling is a huge challenge and has attracted great interest in synthetic and medicinal chemistry. In this study, the first example of Heck-like coupling of cyclic sulfonium salts with alkenes
via
selective C–S bond cleavage using a copper complex as a photosensitizer through a visible-light-driven redox-neutral process is demonstrated. The C–S bond cleavage/Heck-like coupling reaction delivers a variety of corresponding internal alkenes containing aryl alkyl thioethers with good functional group tolerance. This strategy will further expand the new reaction modes of sulfonium salts and provide new insights into the construction of C
sp
3
–C
sp
2
bonds.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D3QO02009F</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Alkenes ; Catalysis ; Chemical reactions ; Cleavage ; Copper ; Copper compounds ; Coupling ; Functional groups ; Salts ; Sulfonium salts ; Thioethers</subject><ispartof>Organic Chemistry Frontiers, 2024-04, Vol.11 (8), p.2195-2200</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-18221a4c348662f3b06dd2bf57bd7a1d3b1070444f2bec961fd651fbbdd4a7753</citedby><cites>FETCH-LOGICAL-c259t-18221a4c348662f3b06dd2bf57bd7a1d3b1070444f2bec961fd651fbbdd4a7753</cites><orcidid>0000-0001-7641-5411 ; 0000-0002-3047-5416</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>Liu, Xianqin</creatorcontrib><creatorcontrib>Li, Xufeng</creatorcontrib><creatorcontrib>Wang, Linyuan</creatorcontrib><creatorcontrib>Shi, Yongjia</creatorcontrib><creatorcontrib>Lv, Jian</creatorcontrib><creatorcontrib>Yang, Daoshan</creatorcontrib><title>Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C–S bond cleavage</title><title>Organic Chemistry Frontiers</title><description>Developing new alkyl electrophiles for the construction of C
sp
3
–C
sp
2
bonds through a Heck-like coupling is a huge challenge and has attracted great interest in synthetic and medicinal chemistry. In this study, the first example of Heck-like coupling of cyclic sulfonium salts with alkenes
via
selective C–S bond cleavage using a copper complex as a photosensitizer through a visible-light-driven redox-neutral process is demonstrated. The C–S bond cleavage/Heck-like coupling reaction delivers a variety of corresponding internal alkenes containing aryl alkyl thioethers with good functional group tolerance. This strategy will further expand the new reaction modes of sulfonium salts and provide new insights into the construction of C
sp
3
–C
sp
2
bonds.</description><subject>Alkenes</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Cleavage</subject><subject>Copper</subject><subject>Copper compounds</subject><subject>Coupling</subject><subject>Functional groups</subject><subject>Salts</subject><subject>Sulfonium salts</subject><subject>Thioethers</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpNkMtKA0EQRRtRMMRs_IICd8KYfswjs5RojBAI4mM79KM6dtKZGadnItm58gf8Q7_EhAhKLaqgDvfCIeSc0StGRT68EQ9zyinNJ0ekx2nCo5jx_PjffUoGISwppYwnKU2yHvl8ccEpj-Dd4rUd6qqusQEtW-m3wQXAUu6-BqaoV5F3KwRddbV35QIUtu-IJUi_whIDyNKA3mrvNITO26p03RqC9G2AjZMQ0KNu3QZh_P3x9Qiq2vMe5UYu8IycWOkDDn53nzxPbp_G02g2v7sfX88izZO8jdiIcyZjLeJRmnIrFE2N4commTKZZEYoRjMax7HlCnWeMmvShFmljIllliWiTy4OuXVTvXUY2mJZdU25qyzETuFe42765PJA6aYKoUFb1I1by2ZbMFrsmeJPtfgBA2tzQA</recordid><startdate>20240416</startdate><enddate>20240416</enddate><creator>Liu, Xianqin</creator><creator>Li, Xufeng</creator><creator>Wang, Linyuan</creator><creator>Shi, Yongjia</creator><creator>Lv, Jian</creator><creator>Yang, Daoshan</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0001-7641-5411</orcidid><orcidid>https://orcid.org/0000-0002-3047-5416</orcidid></search><sort><creationdate>20240416</creationdate><title>Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C–S bond cleavage</title><author>Liu, Xianqin ; Li, Xufeng ; Wang, Linyuan ; Shi, Yongjia ; Lv, Jian ; Yang, Daoshan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-18221a4c348662f3b06dd2bf57bd7a1d3b1070444f2bec961fd651fbbdd4a7753</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkenes</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Cleavage</topic><topic>Copper</topic><topic>Copper compounds</topic><topic>Coupling</topic><topic>Functional groups</topic><topic>Salts</topic><topic>Sulfonium salts</topic><topic>Thioethers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Xianqin</creatorcontrib><creatorcontrib>Li, Xufeng</creatorcontrib><creatorcontrib>Wang, Linyuan</creatorcontrib><creatorcontrib>Shi, Yongjia</creatorcontrib><creatorcontrib>Lv, Jian</creatorcontrib><creatorcontrib>Yang, Daoshan</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Xianqin</au><au>Li, Xufeng</au><au>Wang, Linyuan</au><au>Shi, Yongjia</au><au>Lv, Jian</au><au>Yang, Daoshan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C–S bond cleavage</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2024-04-16</date><risdate>2024</risdate><volume>11</volume><issue>8</issue><spage>2195</spage><epage>2200</epage><pages>2195-2200</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>Developing new alkyl electrophiles for the construction of C
sp
3
–C
sp
2
bonds through a Heck-like coupling is a huge challenge and has attracted great interest in synthetic and medicinal chemistry. In this study, the first example of Heck-like coupling of cyclic sulfonium salts with alkenes
via
selective C–S bond cleavage using a copper complex as a photosensitizer through a visible-light-driven redox-neutral process is demonstrated. The C–S bond cleavage/Heck-like coupling reaction delivers a variety of corresponding internal alkenes containing aryl alkyl thioethers with good functional group tolerance. This strategy will further expand the new reaction modes of sulfonium salts and provide new insights into the construction of C
sp
3
–C
sp
2
bonds.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D3QO02009F</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-7641-5411</orcidid><orcidid>https://orcid.org/0000-0002-3047-5416</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2024-04, Vol.11 (8), p.2195-2200 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
| recordid | cdi_proquest_journals_3039103939 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Alkenes Catalysis Chemical reactions Cleavage Copper Copper compounds Coupling Functional groups Salts Sulfonium salts Thioethers |
| title | Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C–S bond cleavage |
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