Aliphatic C−H oxidation is the most straightforward approach to functionalize hydrocarbon skeletons. The main challenge of this reaction is the control of site selectivity, given the multiple C−H bonds present in any organic molecule. Natural enzymes elegantly solve this problem through the interplay of different interactions that geometrically orient the substrate to expose a single C−H bond to the active unit, thus overriding intrinsic reactivity patterns. A combination of molecular catalysts and supramolecular receptors can be a promising way to replicate such control. This strategy indeed unlocks hydroxylation of C−H bonds that are not accessible with conventional methodologies, in which the selectivity is dictated by the geometry of the substrate–receptor adduct. Herein, we review the reports of recognition-driven C−H oxidation reactions and highlight the key design principles that inspired these works.

Controlling Selectivity in Aliphatic C−H Oxidation through Supramolecular Recognition / Vidal, D.; Olivo, G.; Costas, M.. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 24:20(2018), pp. 5042-5054. [10.1002/chem.201704852]

Controlling Selectivity in Aliphatic C−H Oxidation through Supramolecular Recognition

Olivo G.
;
2018

Abstract

Aliphatic C−H oxidation is the most straightforward approach to functionalize hydrocarbon skeletons. The main challenge of this reaction is the control of site selectivity, given the multiple C−H bonds present in any organic molecule. Natural enzymes elegantly solve this problem through the interplay of different interactions that geometrically orient the substrate to expose a single C−H bond to the active unit, thus overriding intrinsic reactivity patterns. A combination of molecular catalysts and supramolecular receptors can be a promising way to replicate such control. This strategy indeed unlocks hydroxylation of C−H bonds that are not accessible with conventional methodologies, in which the selectivity is dictated by the geometry of the substrate–receptor adduct. Herein, we review the reports of recognition-driven C−H oxidation reactions and highlight the key design principles that inspired these works.
2018
catalysis; C−H oxidation; molecular recognition; selectivity; supramolecular chemistry
01 Pubblicazione su rivista::01g Articolo di rassegna (Review)
Controlling Selectivity in Aliphatic C−H Oxidation through Supramolecular Recognition / Vidal, D.; Olivo, G.; Costas, M.. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 24:20(2018), pp. 5042-5054. [10.1002/chem.201704852]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1552518
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