Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles
A selenium-catalyzed electrosynthesis involving regio- and stereo-selective N-olefination of azoles was developed. The room-temperature reaction was efficient (up to 97 % yield) and compatible with various styrenes and azoles. Mechanistic study showed that the cascade reaction was triggered by the...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2025-05-01
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| Series: | Green Synthesis and Catalysis |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S266655492400005X |
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| author | Kejun Lin Jianyong Lan Lin Hao Tingshun Zhu |
| author_facet | Kejun Lin Jianyong Lan Lin Hao Tingshun Zhu |
| author_sort | Kejun Lin |
| collection | DOAJ |
| description | A selenium-catalyzed electrosynthesis involving regio- and stereo-selective N-olefination of azoles was developed. The room-temperature reaction was efficient (up to 97 % yield) and compatible with various styrenes and azoles. Mechanistic study showed that the cascade reaction was triggered by the selenium-cation-mediated electrophilic trans-aminoselenation, and followed by an oxidative cis-elimination of selane. The electrosynthesis was also well compatible with the more challenging internal alkene substrates, giving the desired N-vinyl azoles in up to 88 % yield and > 20:1 Z/E ratio. |
| format | Article |
| id | doaj-art-56d501759be34b0ca173702bd019065a |
| institution | DOAJ |
| issn | 2666-5549 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj-art-56d501759be34b0ca173702bd019065a2025-08-20T02:43:25ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492025-05-016218318610.1016/j.gresc.2024.01.005Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azolesKejun Lin0Jianyong Lan1Lin Hao2Tingshun Zhu3Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Chemistry, IGCME, Sun Yat-Sen University, Guangzhou 510275, ChinaKey Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Chemistry, IGCME, Sun Yat-Sen University, Guangzhou 510275, ChinaSchool of Chemistry, Chemical Engineering, and Biotechnology, Nanyang Technological University, Singapore 637371, SingaporeKey Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Chemistry, IGCME, Sun Yat-Sen University, Guangzhou 510275, China; Corresponding author.A selenium-catalyzed electrosynthesis involving regio- and stereo-selective N-olefination of azoles was developed. The room-temperature reaction was efficient (up to 97 % yield) and compatible with various styrenes and azoles. Mechanistic study showed that the cascade reaction was triggered by the selenium-cation-mediated electrophilic trans-aminoselenation, and followed by an oxidative cis-elimination of selane. The electrosynthesis was also well compatible with the more challenging internal alkene substrates, giving the desired N-vinyl azoles in up to 88 % yield and > 20:1 Z/E ratio.http://www.sciencedirect.com/science/article/pii/S266655492400005XElectrosynthesisOrganoselenium catalysisVinyl azolesAza-wacker reactionDehydrogenated C-N coupling |
| spellingShingle | Kejun Lin Jianyong Lan Lin Hao Tingshun Zhu Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles Green Synthesis and Catalysis Electrosynthesis Organoselenium catalysis Vinyl azoles Aza-wacker reaction Dehydrogenated C-N coupling |
| title | Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles |
| title_full | Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles |
| title_fullStr | Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles |
| title_full_unstemmed | Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles |
| title_short | Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles |
| title_sort | electrochemical n olefination for the regio and stereo selective synthesis of vinyl azoles |
| topic | Electrosynthesis Organoselenium catalysis Vinyl azoles Aza-wacker reaction Dehydrogenated C-N coupling |
| url | http://www.sciencedirect.com/science/article/pii/S266655492400005X |
| work_keys_str_mv | AT kejunlin electrochemicalnolefinationfortheregioandstereoselectivesynthesisofvinylazoles AT jianyonglan electrochemicalnolefinationfortheregioandstereoselectivesynthesisofvinylazoles AT linhao electrochemicalnolefinationfortheregioandstereoselectivesynthesisofvinylazoles AT tingshunzhu electrochemicalnolefinationfortheregioandstereoselectivesynthesisofvinylazoles |