Fluoride-Promoted Esterification with Imidazolide-Activated Compounds: A Modular and Sustainable Approach to Dendrimers
2015 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 8, 2416-2419 p.Article in journal (Refereed) Published
Based on the growing demand for facile and sustainable synthetic methods to structurally perfect polymers, we herein describe a significant improvement of esterification reactions capitalizing on 1,1-carbonyldiimidazole (CDI). Cesium fluoride was shown to be an essential catalyst for these reactions to reach completion. This approach was successfully applied to the synthesis of structurally flawless and highly functional polyester dendrimers employing traditional and accelerated growth strategies. A sixth generation bis-MPA dendrimer with a molecular weight of 22.080Da and 192 peripheral hydroxy groups was isolated in less than one day of total reaction time. Large quantities of dendrimerswere obtained in high yields (>90%) using simple purification steps under sustainable conditions. The fluoride-promoted esterification (FPE) via imidazolide-activated compounds is wide in scope and constitutes a potentially new approach toward functional polymers and other materials.
Place, publisher, year, edition, pages
2015. Vol. 54, no 8, 2416-2419 p.
Accelerated synthesis, Esterification, Fluoride; Imidazole, Polyester dendrimers
IdentifiersURN: urn:nbn:se:kth:diva-161958DOI: 10.1002/anie.201411370ISI: 000350100000019PubMedID: 25605503ScopusID: 2-s2.0-84922800982OAI: oai:DiVA.org:kth-161958DiVA: diva2:800902
FunderKnut and Alice Wallenberg FoundationMarcus and Amalia Wallenberg FoundationSwedish Research Council, 2011-5358, 2010-435
QC 201504082015-04-082015-03-202015-04-08Bibliographically approved