Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds
Visible light-mediated site-specific C(sp3)-H xanthylation of amides has been accomplished using N-xanthylamides. The N-centered radicals generated by light initiation of N-xanthylamide substrates undergo 1,5-hydrogen atom transfer to form benzylic or alkyl radical intermediates under metal- and cat...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2023-11-01
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| Series: | Green Synthesis and Catalysis |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666554922000758 |
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| author | Hang Chen Yang Zhou Panpan Lei Haifeng Wang Qiongjiao Yan Roberta Properzi Wei Wang Linhai Jing Fener Chen |
| author_facet | Hang Chen Yang Zhou Panpan Lei Haifeng Wang Qiongjiao Yan Roberta Properzi Wei Wang Linhai Jing Fener Chen |
| author_sort | Hang Chen |
| collection | DOAJ |
| description | Visible light-mediated site-specific C(sp3)-H xanthylation of amides has been accomplished using N-xanthylamides. The N-centered radicals generated by light initiation of N-xanthylamide substrates undergo 1,5-hydrogen atom transfer to form benzylic or alkyl radical intermediates under metal- and catalyst-free conditions. This method exhibits a broad substrate scope, high functional group tolerance, and high regioselectivity. Furthermore, this strategy provides straightforward access to a range of derivatives through the subsequent elaboration of the xanthate group. |
| first_indexed | 2024-03-08T18:42:10Z |
| format | Article |
| id | doaj.art-9d0bf8db2f68472999fa80074999113f |
| institution | Directory Open Access Journal |
| issn | 2666-5549 |
| language | English |
| last_indexed | 2024-03-08T18:42:10Z |
| publishDate | 2023-11-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj.art-9d0bf8db2f68472999fa80074999113f2023-12-29T04:46:12ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492023-11-0144350354Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bondsHang Chen0Yang Zhou1Panpan Lei2Haifeng Wang3Qiongjiao Yan4Roberta Properzi5Wei Wang6Linhai Jing7Fener Chen8Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637009, ChinaChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637009, ChinaChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637009, ChinaPharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, ChinaPharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, ChinaMax-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr 45470, GermanyPharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, China; Corresponding authors. Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan, 430205, China.Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637009, China; Corresponding authors. Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan, 430205, China.Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, China; Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China; Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai 200433, China; Corresponding authors. Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan, 430205, China.Visible light-mediated site-specific C(sp3)-H xanthylation of amides has been accomplished using N-xanthylamides. The N-centered radicals generated by light initiation of N-xanthylamide substrates undergo 1,5-hydrogen atom transfer to form benzylic or alkyl radical intermediates under metal- and catalyst-free conditions. This method exhibits a broad substrate scope, high functional group tolerance, and high regioselectivity. Furthermore, this strategy provides straightforward access to a range of derivatives through the subsequent elaboration of the xanthate group.http://www.sciencedirect.com/science/article/pii/S2666554922000758C-H functionalization1,5-Hydrogen atom transferPhotocatalyticSite-specificXanthylation |
| spellingShingle | Hang Chen Yang Zhou Panpan Lei Haifeng Wang Qiongjiao Yan Roberta Properzi Wei Wang Linhai Jing Fener Chen Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds Green Synthesis and Catalysis C-H functionalization 1,5-Hydrogen atom transfer Photocatalytic Site-specific Xanthylation |
| title | Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds |
| title_full | Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds |
| title_fullStr | Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds |
| title_full_unstemmed | Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds |
| title_short | Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds |
| title_sort | visible light driven intramolecular xanthylation of remote unactivated c sp3 h bonds |
| topic | C-H functionalization 1,5-Hydrogen atom transfer Photocatalytic Site-specific Xanthylation |
| url | http://www.sciencedirect.com/science/article/pii/S2666554922000758 |
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