Catalysis of a Diels–Alder Reaction between Azachalcones and Cyclopentadiene by a Recyclable Copper(II)-PEIP Metal-Organic Framework
Ημερομηνία
2023-08-01Συγγραφέας
Hadjikyprianou, EleniPetrides, Sotiris
Kourtellaris, Andreas
Tasiopoulos, Anastasios J.
Georgiades, Savvas N.
ISSN
19961944Εκδότης
Multidisciplinary Digital Publishing Institute (MDPI)Source
MaterialsVolume
16Issue
15Pages
5298-Google Scholar check
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Εμφάνιση πλήρους εγγραφήςΕπιτομή
Metal-organic frameworks (MOFs) have attracted considerable interest as emerging heterogeneous catalysts for organic transformations of synthetic utility. Herein, a Lewis-acidic MOF, {[Cu3(PEIP)2(5-NH2-mBDC)(DMF)]·7DMF}∞, denoted as Cu(ΙΙ)-PEIP, has been synthesized via a one-pot process and deployed as an efficient heterogeneous catalyst for a Diels–Alder cycloaddition. Specifically, the [4 + 2] cycloaddition of 13 substituted azachalcone dienophiles with cyclopentadiene has been investigated. MOF-catalyzed reaction conditions were optimized, leading to the selection of water as the solvent, in the presence of 10% mol sodium dodecyl sulfate (SDS) to address substrate solubility. The Cu(II)-PEIP catalyst showed excellent activity under these green and mild conditions, exhibiting comparable or, in some cases, superior efficiency to a homogeneous catalyst often employed in Diels–Alder reactions, namely, Cu(OTf)2. The nature of the azachalcone substituent played a significant role in the reactivity of the dienophiles, with electron-withdrawing (EW) substituents enhancing conversion and electron-donating (ED) ones exhibiting the opposite effect. Coordinating substituents appeared to enhance the endo selectivity. Importantly, the Cu(II)-PEIP catalyst can be readily isolated from the reaction mixture and recycled up to four times without any significant reduction in conversion or selectivity.
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