Chiral Chromium Salen@rGO as Multipurpose and Recyclable Heterogeneous Catalyst

The first immobilization of a pyrene‐tagged chromium salen complex through π‐π noncovalent interactions on reduced graphene oxide (rGO) is described. A very robust supported catalytic system is obtained to promote asymmetric catalysis in repeated cycles, without loss of activity or enantioselectivit...

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Veröffentlicht in:Chemistry : a European journal 2021-06, Vol.27 (36), p.9454-9460
Hauptverfasser: Abd El Sater, Mariam, Mellah, Mohamed, Dragoe, Diana, Kolodziej, Emilie, Jaber, Nada, Schulz, Emmanuelle
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Sprache:eng
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Zusammenfassung:The first immobilization of a pyrene‐tagged chromium salen complex through π‐π noncovalent interactions on reduced graphene oxide (rGO) is described. A very robust supported catalytic system is obtained to promote asymmetric catalysis in repeated cycles, without loss of activity or enantioselectivity. This specific behavior was demonstrated in two different catalytic reactions (up to ten reuses) promoted by chromium salen complexes, the cyclohexene oxide ring‐opening reaction and the hetero‐Diels‐Alder cycloaddition between various aldehydes and Danishefsky's diene. Furthermore, the chiral chromium salen@rGO has been found to be compatible with a multi‐substrate type use, in which the structure of the substrate involved is modified each time the catalyst is reused. A pyrene‐tagged Cr‐salen complex immobilized by π‐π interactions at rGO surface delivers a robust, reusable, heterogeneous catalyst that is efficient in several asymmetric catalytic reactions. Highly enantioenriched compounds were produced and various valuable scalemic compounds were easily isolated in their pure form even when the catalyst was engaged in a multisubstrate procedure.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202101003