An efficient metal-free organocatalytic activation of hydrogen peroxide (H2O2) towards thioethers leading to the corresponding sulfoxides in high yields at room temperature within hours was promoted by the hexameric capsule formed by the self-assembly of resorcin[4]arene units. The capsule plays a dual role of activating the oxidant through hydrogen bonding and favouring the oxidation reaction inside the cavity. Inactivation of the supramolecular organocatalyst was observed by using competitive ammonium guests, mimicking the inactivation of enzymes by competitive inhibitors

An efficient metal-free organocatalytic activation of hydrogen peroxide (H2O2) towards thioethers leading to the corresponding sulfoxides in high yields at room temperature within hours was promoted by the hexameric capsule formed by the self-assembly of resorcin[4]arene units. The capsule plays a dual role of activating the oxidant through hydrogen bonding and favouring the oxidation reaction inside the cavity. Inactivation of the supramolecular organocatalyst was observed by using competitive ammonium guests, mimicking the inactivation of enzymes by competitive inhibitors.

Supramolecular Activation of Hydrogen Peroxide in the Selective Sulfoxidation of Thioethers by a Self-Assembled Hexameric Capsule

LA SORELLA, GIORGIO;SPERNI, Laura;STRUKUL, Giorgio;SCARSO, Alessandro
2016

Abstract

An efficient metal-free organocatalytic activation of hydrogen peroxide (H2O2) towards thioethers leading to the corresponding sulfoxides in high yields at room temperature within hours was promoted by the hexameric capsule formed by the self-assembly of resorcin[4]arene units. The capsule plays a dual role of activating the oxidant through hydrogen bonding and favouring the oxidation reaction inside the cavity. Inactivation of the supramolecular organocatalyst was observed by using competitive ammonium guests, mimicking the inactivation of enzymes by competitive inhibitors
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10278/3677766
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