Taking electrodecarboxylative etherification beyond Hofer–Moest using a radical C–O coupling strategy
- Established electrodecarboxylative etherification protocols are based on Hofer-Moest-type reaction pathways. An oxidative decarboxylation gives rise to radicals, which are further oxidised to carbocations. This is possible only for benzylic or otherwise stabilised substrates. Here, we report the electrodecarboxylative radical-radical coupling of lithium alkylcarboxylates with 1-hydroxybenzotriazole at platinum electrodes in methanol/pyridine to afford alkyl benzotriazole ethers. The substrate scope of this electrochemical radical coupling extends to primary and secondary alkylcarboxylates. The benzotriazole products easily undergo reductive cleavage to the alcohols. They can also serve as synthetic hubs to access a wide variety of functional groups. This reaction prototype demonstrates that electrodecarboxylative C–O bond formation can be taken beyond the intrinsic substrate limitations of Hofer-Moest mechanisms.
| Author: | Ángel Manu MartínezGND, Davit HayrapetyanGND, Tim van LingenORCiDGND, Marco DygaORCiDGND, Lukas J. GooßenORCiDGND |
|---|---|
| URN: | urn:nbn:de:hbz:294-94326 |
| DOI: | https://doi.org/10.1038/s41467-020-18275-1 |
| Parent Title (English): | Nature communications |
| Publisher: | Nature Publishing Group UK |
| Place of publication: | London |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2022/11/17 |
| Date of first Publication: | 2020/09/02 |
| Publishing Institution: | Ruhr-Universität Bochum, Universitätsbibliothek |
| Volume: | 11 |
| Issue: | Article 4407 |
| First Page: | 4407-1 |
| Last Page: | 4407-8 |
| Note: | Dieser Beitrag ist auf Grund des DEAL-Springer-Vertrages frei zugänglich. |
| Dewey Decimal Classification: | Naturwissenschaften und Mathematik / Chemie, Kristallographie, Mineralogie |
| open_access (DINI-Set): | open_access |
| faculties: | Fakultät für Chemie und Biochemie |
| Licence (English): |  Creative Commons - CC BY 4.0 - Attribution 4.0 International |
