Carvalho Ribeiro, Jhully Anne Barros;
Rodini Mattioli, Renan;
Browne, Duncan L;
Pastre, Julio C;
(2025)
Mechanochemical synthesis of phthalimides from
terpenes via tandem Diels-Alder cycloaddition and
iodine-mediated aromatization.
RSC Sustainability
10.1039/d5su00509d.
(In press).
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Abstract
A solvent-minimized, two-step mechanochemical protocol has been developed for the synthesis of terpene-derived phthalimides via sequential Diels–Alder cycloaddition and iodine-mediated aromatization at room temperature. Efficient conversion of isoprene and maleimides by ball-milling yields adducts in up to 86% yield, followed by in situ aromatization using iodine and 1,1,3,3-tetramethylguanidine to furnish phthalimides in up to 82% yield. The process tolerates a range of functional groups and is sensitive to steric hindrance around the diene and dienophile. This method circumvents conventional thermal protocols, offering a scalable and operationally simple route to value-added aromatics from renewable feedstocks under ambient conditions.
| Type: | Article |
|---|---|
| Title: | Mechanochemical synthesis of phthalimides from terpenes via tandem Diels-Alder cycloaddition and iodine-mediated aromatization |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/d5su00509d |
| Publisher version: | https://doi.org/10.1039/d5su00509d |
| Language: | English |
| Additional information: | © 2025 The Author(s). Published by the Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence (https://creativecommons.org/licenses/by-nc/3.0/deed.en). |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10216949 |
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