Visible‐Light‐Induced Mpg‐C3N4 Catalyzed C(sp2)−H Thiocyanation of Ketene Dithioacetals
Using mesoporous graphite carbon nitride (mpg‐C3N4) as metal‐free heterogeneous catalyst, the thiocyanation of ketene dithioacetals was achieved under visible light irradiation with oxygen as green oxidant and without any other additives. The present protocol has excellent functional group tolerance...
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| Veröffentlicht in: | European journal of organic chemistry 2025-01, Vol.28 (4), p.n/a |
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| container_title | European journal of organic chemistry |
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| creator | Yin, Fumeng Hu, Shan Zhu, Shuwei Xing, Shifeng Zhu, Hongjun |
| description | Using mesoporous graphite carbon nitride (mpg‐C3N4) as metal‐free heterogeneous catalyst, the thiocyanation of ketene dithioacetals was achieved under visible light irradiation with oxygen as green oxidant and without any other additives. The present protocol has excellent functional group tolerance and the desired tetrasubstituted alkenyl thiocyanides were obtained in moderate to good yields. Moreover, the recyclable mpg‐C3N4 catalyst could be used at least 6 times without significant loss of activities. A series of mechanistic validation experiments indicated that the reaction involves a radical process.
Using mesoporous graphitic carbon nitride (mpg‐C3N4) as a metal‐free heterogeneous photocatalyst was developed for thiocyanation of alkenes under visible light irradiation with oxygen as green oxidant and without any other additives. The present protocol has excellent functional group tolerance and the desired tetrasubstituted alkenyl thiocyanides were obtained in moderate to good yields. Moreover, the recyclable mpg‐C3N4 catalyst could be used at least 6 times without significant loss of activities. |
| doi_str_mv | 10.1002/ejoc.202401180 |
| format | Article |
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Using mesoporous graphitic carbon nitride (mpg‐C3N4) as a metal‐free heterogeneous photocatalyst was developed for thiocyanation of alkenes under visible light irradiation with oxygen as green oxidant and without any other additives. The present protocol has excellent functional group tolerance and the desired tetrasubstituted alkenyl thiocyanides were obtained in moderate to good yields. Moreover, the recyclable mpg‐C3N4 catalyst could be used at least 6 times without significant loss of activities.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202401180</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Carbon nitride ; Catalysts ; C−H thiocyanation ; Functional groups ; Internal alkenes ; Light irradiation ; Mesoporous graphitic carbon nitride ; Metal-free ; Oxidizing agents ; Photocatalysis</subject><ispartof>European journal of organic chemistry, 2025-01, Vol.28 (4), p.n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><rights>2025 Wiley-VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0003-1650-541X</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%2Fejoc.202401180$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202401180$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Yin, Fumeng</creatorcontrib><creatorcontrib>Hu, Shan</creatorcontrib><creatorcontrib>Zhu, Shuwei</creatorcontrib><creatorcontrib>Xing, Shifeng</creatorcontrib><creatorcontrib>Zhu, Hongjun</creatorcontrib><title>Visible‐Light‐Induced Mpg‐C3N4 Catalyzed C(sp2)−H Thiocyanation of Ketene Dithioacetals</title><title>European journal of organic chemistry</title><description>Using mesoporous graphite carbon nitride (mpg‐C3N4) as metal‐free heterogeneous catalyst, the thiocyanation of ketene dithioacetals was achieved under visible light irradiation with oxygen as green oxidant and without any other additives. The present protocol has excellent functional group tolerance and the desired tetrasubstituted alkenyl thiocyanides were obtained in moderate to good yields. Moreover, the recyclable mpg‐C3N4 catalyst could be used at least 6 times without significant loss of activities. A series of mechanistic validation experiments indicated that the reaction involves a radical process.
Using mesoporous graphitic carbon nitride (mpg‐C3N4) as a metal‐free heterogeneous photocatalyst was developed for thiocyanation of alkenes under visible light irradiation with oxygen as green oxidant and without any other additives. The present protocol has excellent functional group tolerance and the desired tetrasubstituted alkenyl thiocyanides were obtained in moderate to good yields. Moreover, the recyclable mpg‐C3N4 catalyst could be used at least 6 times without significant loss of activities.</description><subject>Carbon nitride</subject><subject>Catalysts</subject><subject>C−H thiocyanation</subject><subject>Functional groups</subject><subject>Internal alkenes</subject><subject>Light irradiation</subject><subject>Mesoporous graphitic carbon nitride</subject><subject>Metal-free</subject><subject>Oxidizing agents</subject><subject>Photocatalysis</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2025</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNo9ULFOwzAQtRBIlMLKHIkFhpQ7O7HrEYVCC4UuBbFZTmq3rkoSklQoTIyMiE_sl2BU1Ondu3vvTvcIOUXoIQC9NMsi61GgESD2YY90EKQMgUvY93XEohAlezkkR3W9BADJOXaIena1S1dm8_k9dvNF43GUz9aZmQUP5dyzhD1GQaIbvWo_fDM5r0t6sfn6GQbThSuyVue6cUUeFDa4N43JTXDtGj_RmfGe-pgcWA_m5B-75OlmME2G4XhyO0quxmGJnEHIWEoji5LyVGQpQGx03KeCY8wk1YIKYVKZxtZyHRvbBwrIhBD-bQvgJaxLzrZ7y6p4W5u6UctiXeX-pGIYS8mBe0uXyK3q3a1Mq8rKveqqVQjqL0H1l6DaJagGd5Nkx9gv4NhohA</recordid><startdate>20250124</startdate><enddate>20250124</enddate><creator>Yin, Fumeng</creator><creator>Hu, Shan</creator><creator>Zhu, Shuwei</creator><creator>Xing, Shifeng</creator><creator>Zhu, Hongjun</creator><general>Wiley Subscription Services, Inc</general><scope/><orcidid>https://orcid.org/0000-0003-1650-541X</orcidid></search><sort><creationdate>20250124</creationdate><title>Visible‐Light‐Induced Mpg‐C3N4 Catalyzed C(sp2)−H Thiocyanation of Ketene Dithioacetals</title><author>Yin, Fumeng ; Hu, Shan ; Zhu, Shuwei ; Xing, Shifeng ; Zhu, Hongjun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p1630-33b24f1926b7cb005ea5827615392a7277eb9b5ff6a5ef802013777002f003923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2025</creationdate><topic>Carbon nitride</topic><topic>Catalysts</topic><topic>C−H thiocyanation</topic><topic>Functional groups</topic><topic>Internal alkenes</topic><topic>Light irradiation</topic><topic>Mesoporous graphitic carbon nitride</topic><topic>Metal-free</topic><topic>Oxidizing agents</topic><topic>Photocatalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yin, Fumeng</creatorcontrib><creatorcontrib>Hu, Shan</creatorcontrib><creatorcontrib>Zhu, Shuwei</creatorcontrib><creatorcontrib>Xing, Shifeng</creatorcontrib><creatorcontrib>Zhu, Hongjun</creatorcontrib><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yin, Fumeng</au><au>Hu, Shan</au><au>Zhu, Shuwei</au><au>Xing, Shifeng</au><au>Zhu, Hongjun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible‐Light‐Induced Mpg‐C3N4 Catalyzed C(sp2)−H Thiocyanation of Ketene Dithioacetals</atitle><jtitle>European journal of organic chemistry</jtitle><date>2025-01-24</date><risdate>2025</risdate><volume>28</volume><issue>4</issue><epage>n/a</epage><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Using mesoporous graphite carbon nitride (mpg‐C3N4) as metal‐free heterogeneous catalyst, the thiocyanation of ketene dithioacetals was achieved under visible light irradiation with oxygen as green oxidant and without any other additives. The present protocol has excellent functional group tolerance and the desired tetrasubstituted alkenyl thiocyanides were obtained in moderate to good yields. Moreover, the recyclable mpg‐C3N4 catalyst could be used at least 6 times without significant loss of activities. A series of mechanistic validation experiments indicated that the reaction involves a radical process.
Using mesoporous graphitic carbon nitride (mpg‐C3N4) as a metal‐free heterogeneous photocatalyst was developed for thiocyanation of alkenes under visible light irradiation with oxygen as green oxidant and without any other additives. The present protocol has excellent functional group tolerance and the desired tetrasubstituted alkenyl thiocyanides were obtained in moderate to good yields. Moreover, the recyclable mpg‐C3N4 catalyst could be used at least 6 times without significant loss of activities.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202401180</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-1650-541X</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Carbon nitride Catalysts C−H thiocyanation Functional groups Internal alkenes Light irradiation Mesoporous graphitic carbon nitride Metal-free Oxidizing agents Photocatalysis |
| title | Visible‐Light‐Induced Mpg‐C3N4 Catalyzed C(sp2)−H Thiocyanation of Ketene Dithioacetals |
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