Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles
An efficient and eco-friendly approach for synthesizing difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles was established via a visible-light-promoted radical cyclization reaction. This method employed the readily accessible and inexpensive CF2HCO2H or PhCF2COOH, along with be...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.15 |
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| author | Yujun Pang Jinglan Yan Nawaf Al-Maharik Qian Zhang Zeguo Fang Dong Li |
| author_facet | Yujun Pang Jinglan Yan Nawaf Al-Maharik Qian Zhang Zeguo Fang Dong Li |
| author_sort | Yujun Pang |
| collection | DOAJ |
| description | An efficient and eco-friendly approach for synthesizing difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles was established via a visible-light-promoted radical cyclization reaction. This method employed the readily accessible and inexpensive CF2HCO2H or PhCF2COOH, along with benzimidazoles bearing unactivated alkenes and PhI(OAc)2 as substrates, and proceeded without the need of any base, metal catalyst, photocatalyst or additive. In total, 24 examples were examined, and all of them successfully underwent cyclization reaction to produce the target products in good to excellent yields. Mechanistic studies revealed that the reaction proceeds via a radical pathway. |
| format | Article |
| id | doaj-art-034b95c7efb14225ad85857e611c3145 |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-034b95c7efb14225ad85857e611c31452025-02-03T09:10:17ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-01-0121123424110.3762/bjoc.21.151860-5397-21-15Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazolesYujun Pang0Jinglan Yan1Nawaf Al-Maharik2Qian Zhang3Zeguo Fang4Dong Li5New Materials and Green Manufacturing Talent Introduction and Innovation Demonstration Base, Hubei University of Technology, 430068 Wuhan, China New Materials and Green Manufacturing Talent Introduction and Innovation Demonstration Base, Hubei University of Technology, 430068 Wuhan, China Department of chemistry, Faculty of Science, An Najah National University, Nablus, Palestine New Materials and Green Manufacturing Talent Introduction and Innovation Demonstration Base, Hubei University of Technology, 430068 Wuhan, China New Materials and Green Manufacturing Talent Introduction and Innovation Demonstration Base, Hubei University of Technology, 430068 Wuhan, China New Materials and Green Manufacturing Talent Introduction and Innovation Demonstration Base, Hubei University of Technology, 430068 Wuhan, China An efficient and eco-friendly approach for synthesizing difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles was established via a visible-light-promoted radical cyclization reaction. This method employed the readily accessible and inexpensive CF2HCO2H or PhCF2COOH, along with benzimidazoles bearing unactivated alkenes and PhI(OAc)2 as substrates, and proceeded without the need of any base, metal catalyst, photocatalyst or additive. In total, 24 examples were examined, and all of them successfully underwent cyclization reaction to produce the target products in good to excellent yields. Mechanistic studies revealed that the reaction proceeds via a radical pathway.https://doi.org/10.3762/bjoc.21.15cyclizationdifluoromethylationhypervalent iodinepolycyclic imidazolevisible light |
| spellingShingle | Yujun Pang Jinglan Yan Nawaf Al-Maharik Qian Zhang Zeguo Fang Dong Li Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles Beilstein Journal of Organic Chemistry cyclization difluoromethylation hypervalent iodine polycyclic imidazole visible light |
| title | Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles |
| title_full | Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles |
| title_fullStr | Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles |
| title_full_unstemmed | Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles |
| title_short | Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles |
| title_sort | visible light promoted radical cyclisation of unactivated alkenes in benzimidazoles synthesis of difluoromethyl and aryldifluoromethyl substituted polycyclic imidazoles |
| topic | cyclization difluoromethylation hypervalent iodine polycyclic imidazole visible light |
| url | https://doi.org/10.3762/bjoc.21.15 |
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