Green synthesis of calixarenes derivatives: Mechanochemical-assisted key steps

Submitting author affiliation:
Instituto Superior Técnico, Lisbon, Portugal

Beilstein Arch. 2023, 202340.

Published 29 Sep 2023

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This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.


Calixarenes are important scaffolds in the field of nanosciences, from sensing to therapeutics. Its synthesis and functionalization are still a challenging task, and new synthetic protocols are highly desirable. The selective functionalization of the lower rim of calix[4]arenes has been successfully achieved using a mechanochemical strategy, enabling a more sustainable and time-saving route, an easier synthesis and precluding the use of organic solvents. For comparison, the reactions were performed in a stainless-steel vibratory mill and in a planetary ball mill employing both stainless steel and zirconium oxide reactors. Using 25,26,27-tri-O-propyl-28-hydroxy-p-tert-butylcalix[4]arene 6 as the precursor, four advanced functional calixarenes were prepared, and the yields and experimental conditions compared with the conventional synthesis. For planetary-assisted grinding, the best results were obtained when the zirconium oxide reactor was used. In some cases, the vibratory-assisted grinding gave higher yields, thus showing the importance of the milling machine in the synthesis of this macromolecules. The effect of the balls number and size on the reactions yield was also explored.

Keywords: mechanosynthesis; green chemistry; calixarenes; Sonogashira–Hagihara cross-coupling

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Silveiro, C.; Bonifácio, V. D. B.; Prata, J. V.; Costa, A. I.; Barata, P. D. Beilstein Arch. 2023, 202340. doi:10.3762/bxiv.2023.40.v1

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