A bidentate iodine(III)-based halogen-bond donor as a powerful organocatalyst
- In contrast to iodine(I)-based halogen bond donors, iodine(III)-derived ones have only been used as Lewis acidic organocatalysts in a handful of examples, and in all cases they acted in a monodentate fashion. Herein, we report the first application of a bidentate bis(iodolium) salt as organocatalyst in a Michael and a nitro-Michael addition reaction as well as in a Diels–Alder reaction that had not been activated by noncovalent organocatalysts before. In all cases, the performance of this bidentate XB donor distinctly surpassed the one of arguably the currently strongest iodine(I)-based organocatalyst. Bidentate coordination to the substrate was corroborated by a structural analysis and by DFT calculations of the transition states. Overall, the catalytic activity of the bis(iodolium) system approaches that of strong Lewis acids like BF\(_3\).
| Author: | Flemming HeinenGND, Dominik L. ReinhardORCiDGND, Elric EngelageORCiDGND, Stefan M. HuberORCiDGND |
|---|---|
| URN: | urn:nbn:de:hbz:294-112156 |
| DOI: | https://doi.org/10.1002/anie.202013172 |
| Parent Title (German): | Angewandte Chemie International Edition |
| Publisher: | Wiley-VCH |
| Place of publication: | Weinheim |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2024/08/29 |
| Date of first Publication: | 2020/11/20 |
| Publishing Institution: | Ruhr-Universität Bochum, Universitätsbibliothek |
| Tag: | Diels–Alder cycloaddition; halogen bonding; hypervalent iodine; noncovalent interactions; organocatalysis |
| Volume: | 60 |
| Issue: | 10 |
| First Page: | 5069 |
| Last Page: | 5073 |
| Note: | Dieser Beitrag ist auf Grund des DEAL-Wiley-Vertrages frei zugänglich. |
| Institutes/Facilities: | Lehrstuhl für Organische Chemie II |
| 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 |
