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

Javier RamosSoriano | Zendy; José J. Reina | Zendy; Beatriz M. Illescas | Zendy; Javier Rojo | Zendy; Nazario Martı́n | Zendy

Open Access

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

Author(s) -

Javier RamosSoriano,

José J. Reina,

Beatriz M. Illescas,

Javier Rojo,

Nazario Martı́n

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b02402

Subject(s) - maleimide , adduct , fullerene , click chemistry , chemistry , biocompatible material , fullerene chemistry , polymer chemistry , copper , combinatorial chemistry , derivative (finance) , organic chemistry , medicine , economics , biomedical engineering , financial economics

The 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.

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