Carbonyl activation by selenium‐ and tellurium‐based chalcogen bonding in a Michael addition reaction
- In the last years the use of chalcogen bonding — the noncovalent interaction involving electrophilic chalcogen centers — in noncovalent organocatalysis has received increased interest, particularly regarding the use of intermolecular Lewis acids. Herein, we present the first use of tellurium‐based catalysts for the activation of a carbonyl compound (and only the second such activation by chalcogen bonding in general). As benchmark reaction, the Michael‐type addition between \(\it trans\)‐crotonophenone and 1‐methylindole (and its derivatives) was investigated in the presence of various catalyst candidates. Whereas non‐chalcogen‐bonding reference compounds were inactive, strong rate accelerations of up to 1000 could be achieved by bidentate triazolium‐based chalcogen bond donors, with product yields of >90 % within 2 h of reaction time. Organotellurium derivatives were markedly more active than their selenium and sulphur analogues and non‐coordinating counterions like \(BAr^{F}_4\) provide the strongest dicationic catalysts.
| Author: | Patrick WonnerGND, Tim SteinkeGND, Lukas VogelGND, Stefan M. HuberORCiDGND |
|---|---|
| URN: | urn:nbn:de:hbz:294-73920 |
| DOI: | https://doi.org/10.1002/chem.201905057 |
| Parent Title (English): | Chemistry |
| Publisher: | Wiley-VCH Verlag |
| Place of publication: | Weinheim |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2020/08/06 |
| Date of first Publication: | 2019/11/14 |
| Publishing Institution: | Ruhr-Universität Bochum, Universitätsbibliothek |
| Tag: | XBCBCAT, Project ID: 638337 Lewis acid catalysis; carbonyl activation; chalcogen bonding; chalcogens; non-covalent organocatalysis |
| Volume: | 26 |
| Issue: | 6 |
| First Page: | 1258 |
| Last Page: | 1262 |
| Note: | Projekt XBCBCAT, Project ID: 638337 |
| Note: | Dieser Beitrag ist auf Grund des DEAL-Wiley-Vertrages frei zugänglich. |
| Relation (DC): | info:eu-repo/grantAgreement/EC/H2020/638337 |
| Dewey Decimal Classification: | Naturwissenschaften und Mathematik / Chemie, Kristallographie, Mineralogie |
| open_access (DINI-Set): | open_access |
| OpenAIRE: | OpenAIRE |
| faculties: | Fakultät für Chemie und Biochemie |
| Licence (English): |  Creative Commons - CC BY 4.0 - Attribution 4.0 International |
