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

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Ramos Soriano, Javier and Reina, José J. and Illescas, Beatriz M. and Rojo, Javier and Martín, Nazario (2018) Maleimide and Cyclooctyne-Based Hexakis-Adducts of Fullerene: Multivalent Scaffolds for Copper-Free Click Chemistry on Fullerenes. Journal of organic chemistry, 83 (4). pp. 1727-1736. ISSN 0022-3263 (Print)1520-6904 (Online)

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Official URL: https://pubs.acs.org/doi/pdf/10.1021/acs.joc.7b02402



Abstract

The synthesis of multivalent systems based on hexakisadducts 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.


Item Type:Article
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:46622
Deposited On:26 Feb 2018 12:32
Last Modified:09 Jan 2019 00:01

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