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Disclosing Cyclic(Alkyl)(Amino)Carbenes as One-Electron Reductants: Synthesis of Acyclic(Amino)(Aryl)Carbene-Based Kekulé Diradicaloids
- Herein, we disclose cyclic(alkyl)(amino)carbenes (CAACs) to be one-electron reductants under the formation of a transient radical cation as indicated by EPR spectroscopy. The disclosed CAAC reducing reactivity was used to synthesize acyclic(amino)(aryl)carbene-based Thiele and Chichibabin hydrocarbons, a new class of Kekulé diradicaloids. The results demonstrate CAACs to be potent organic reductants. Notably, the acyclic(amino)(aryl)carbene-based Chichibabin's hydrocarbon shows an appreciable population of the triplet state at room temperature, as evidenced by both variable-temperature NMR and EPR spectroscopy.
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| Author: | Avijit Maiti, Benedict J. Elvers, Sachinath Bera, Felix Lindl, Ivo Krummenacher, Prasanta Ghosh, Holger Braunschweig, Cem B. Yildiz, Carola Schulzke, Anukul Jana |
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| URN: | urn:nbn:de:gbv:9-opus-106749 |
| DOI: | https://doi.org/10.1002/chem.202104567 |
| ISSN: | 1521-3765 |
| Parent Title (English): | Chemistry: A European Journal |
| Publisher: | Wiley |
| Place of publication: | Hoboken, NJ |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2022/03/09 |
| Date of first Publication: | 2022/05/16 |
| Release Date: | 2024/02/19 |
| Tag: | EPR spectroscopy; carbene; electrochemistry; radical cation; reductant |
| Volume: | 28 |
| Issue: | 28 |
| Article Number: | e202104567 |
| Page Number: | 6 |
| Faculties: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie |
| Collections: | weitere DFG-förderfähige Artikel |
| Licence (German): |  Creative Commons - Namensnennung-Nicht kommerziell-Keine Bearbeitung 4.0 International |