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Maleimide and Cyclooctyne-Based Hexakis-Adducts of Fullerene: Multivalent Scaffolds for Copper-Free Click Chemistry on Fullerenes

AutorRamos-Soriano, Javier; Reina, José J. ; Illescas, Beatriz M.; Rojo, Javier ; Martín, Nazario
Fecha de publicación2018
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 83: 1727- 1736 (2018)
ResumenThe synthesis of multivalent systems based on hexakis-adducts of [60]fullerene employing a biocompatible copper-free click chemistry strategy has been accomplished. A symmetric hexakis-adduct of fullerene bearing 12 maleimide units (3) is reported, and it has been employed to carry out the thiol-maleimide Michael addition. To achieve orthogonal click addition, an asymmetric derivative bearing one maleimide and 10 cyclooctynes has been synthesized. The sequential and one-pot transformations of the two clickable groups have been explored, finding the best results in the case of the one-pot experiment. This route has been used to obtain a biocompatible hexakis-adduct appended with two different biomolecules, carbohydrates, and amino acids.
URIhttp://hdl.handle.net/10261/173211
Identificadoresdoi: 10.1021/acs.joc.7b02402
issn: 1520-6904
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