Monobromination of Cubane 1,4-Diester, A Synthetic Handle for Fluorosulfonylation and Giese-Type Reactions
The bromination of cubane 1,4-diester is described for the first time. The versatility of the C-Br bond for forging C-S and C-C bonds was demonstrated. The fluorosulfonylation reaction allowed the first entry of the cubane in click chemistry illustrated with nucleophiles, electrophiles, and alkynes. The grafting of appendages was illustrated with amino acids and dipeptides, enabling the discrimination of the diesters via cyclization into "fused cubane-lactam" structures.
Authors
- Daniela Vuluga (ORCID: https://orcid.org/0000-0001-9601-0411)
- Bruno Linclau (ORCID: https://orcid.org/0000-0001-8762-0170)
- Catherine Fressigné (ORCID: https://orcid.org/0000-0002-3101-6385)
- Julien Legros (ORCID: https://orcid.org/0000-0002-4807-7897)
- Laly Donnier-Valentin
Institutions
- Centre National de la Recherche Scientifique (FR)
- École Nationale Supérieure d'Ingénieurs de Caen (FR)
- Ghent University (BE)
- Normandie Université (FR)
- Polymères, Biopolymères, Surfaces (FR)
- Université de Rouen Normandie (FR)
- Institut National des Sciences Appliquées Rouen Normandie (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c00967
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- Indian National Science Academy
- Agence Nationale de la Recherche
- Fonds Wetenschappelijk Onderzoek
- Labex
- Centre National de la Recherche Scientifique
- Université de Rouen
- Institut National des Sciences Appliquées Rouen
- Vlaamse regering
- Institut Carnot Santé Animale
- Région Normandie
- European Regional Development Fund