Chalcogen bonding catalysis of a nitro-Michael reaction
- Chalcogen bonding is the non‐covalent interaction between Lewis acidic chalcogen substituents and Lewis bases. Herein, we present the first application of dicationic tellurium‐based chalcogen bond donors in the nitro‐Michael reaction between \(\it trans\) ‐\(\beta\)‐nitrostyrene and indoles. This also constitutes the first activation of nitro derivatives by chalcogen bonding (and halogen bonding). The catalysts showed rate accelerations of more than a factor of 300 compared to strongly Lewis acidic hydrogen bond donors. Several comparison experiments, titrations, and DFT calculations support a chalcogen‐bonding‐based mode of activation of \(\beta\)‐nitrostyrene.
| Author: | Patrick WonnerGND, Alexander DregerGND, Lukas VogelGND, Elric EngelageORCiDGND, Stefan M. HuberORCiDGND |
|---|---|
| URN: | urn:nbn:de:hbz:294-71723 |
| DOI: | https://doi.org/10.1002/anie.201910639 |
| Parent Title (German): | Angewandte Chemie |
| Publisher: | Wiley-VCH Verlag |
| Place of publication: | Weinheim |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2020/05/22 |
| Date of first Publication: | 2019/09/19 |
| Publishing Institution: | Ruhr-Universität Bochum, Universitätsbibliothek |
| Tag: | XBCBCAT, Project ID: 638337 Lewis acids; Michael addition; chalcogen bonding; non-covalent interactions; organocatalysis |
| Volume: | 58 |
| Issue: | 47 |
| First Page: | 16923 |
| Last Page: | 16927 |
| Note: | Dieser Beitrag ist auf Grund des DEAL-Wiley-Vertrages frei zugänglich. |
| Note: | Projekt XBCBCAT, Project ID: 638337 |
| Relation (DC): | info:eu-repo/grantAgreement/EC/H2020/638337 |
| open_access (DINI-Set): | open_access |
| OpenAIRE: | OpenAIRE |
| faculties: | Fakultät für Chemie und Biochemie |
| Licence (German): |  Creative Commons - CC BY-NC-ND 4.0 - Namensnennung - Nicht kommerziell - Keine Bearbeitungen 4.0 International |
