Anodic Desulfurization of Heterocyclic Thiones – A Synthesis to Imidazoles and Analogues
An electrochemical desulfurization of 2-mercapto-imidazoles to the corresponding imidazole is established. This novel anodic transformation is bromide-mediated and easy to conduct in the simplest electrochemical setup, consisting of an undivided cell, carbon electrodes, and constant current electrolysis. The method proved successful in 14 diverse examples of imidazoles and triazoles with up to a 97% yield. The scalability was proven in the multigram synthesis of a technically relevant N-heterocyclic carbene (NHC) ligand precursor.
Authors
- Dainis Kaldre (ORCID: https://orcid.org/0000-0003-3076-3175)
- Kurt Puentener
- Filippo Sladojevich (ORCID: https://orcid.org/0000-0002-4631-8124)
- Siegfried R. Waldvogel (ORCID: https://orcid.org/0000-0002-7949-9638)
- Fabio Falivene
- Philip Arnold
- Davide Cesca
Institutions
- Karlsruhe Institute of Technology (DE)
- Roche (Switzerland) (CH)
- Johannes Gutenberg University Mainz (DE)
- Max Planck Institute for Chemical Energy Conversion (DE)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-28
- DOI
- https://doi.org/10.1021/acs.orglett.4c03413
- Citations
- 3
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- Deutsche Forschungsgemeinschaft
- Max-Planck-Gesellschaft