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...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2024
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/178631 |
| Summary: | 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. |
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