Monobromination of Cubane 1,4-Diester, A Synthetic Handle for Fluorosulfonylation and Giese-Type Reactions
Year: 2025
Type: article
Abstract: 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.
Source: Organic Letters
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
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
Awards: G1576599217, G2900821844, G4356253665, G4656594441, Fluorinations with implications: enhancing the potential of biologically and medicinally interesting molecules through targeted fluorine introduction, G5976147578, G6016564, Synthèse Organique : des molécules au vivant, G799363536, Taming and Exploiting the Reactivity of Cubanes
OpenAlex ID: W4409409955