Unusual Reaction of Isocyanides with Aromatic Aldehydes Catalyzed by a Supramolecular Capsule
The supramolecular resorcinarene hexameric capsule efficiently promotes the unprecedented reaction between isocyanides and electron-deficient aromatic aldehydes leading to the formation of imines and carbon monoxide. The mechanism of the reaction was investigated via isotope labelling, kinetic analysis of the reaction, computational studies and the independent synthesis of a proposed intermediate. Control experiments indicate that the formation of the key aziridinone intermediate is limited to the cavity of the capsule.
Authors
- Bernd Goldfuß (ORCID: https://orcid.org/0000-0002-1814-8818)
- Fabrizio Menchini Fabris (ORCID: https://orcid.org/0000-0001-9209-1680)
- Alessandro Prescimone (ORCID: https://orcid.org/0000-0002-3631-5210)
- Konrad Tiefenbacher (ORCID: https://orcid.org/0000-0002-3351-6121)
- Alessandro Scarso (ORCID: https://orcid.org/0000-0001-6114-9181)
- Jesper M. Köster
- GiovanniMaria Piccini (ORCID: https://orcid.org/0000-0002-3511-4281)
- Luca Fiorini
Institutions
- University of Modena and Reggio Emilia (IT)
- Ca' Foscari University of Venice (IT)
- University of Cologne (DE)
- University of Basel (CH)
- ETH Zurich (CH)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2024-12-23
- DOI
- https://doi.org/10.1002/chem.202404061
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00