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Supramolecular Activation of Hydrogen Peroxide in the Selective Sulfoxidation of Thioethers by a Self‐Assembled Hexameric Capsule
Author(s) -
La Sorella Giorgio,
Sperni Laura,
Strukul Giorgio,
Scarso Alessandro
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600430
Subject(s) - chemistry , hydrogen peroxide , supramolecular chemistry , capsule , hydrogen bond , catalysis , calixarene , combinatorial chemistry , organocatalysis , polymer chemistry , photochemistry , organic chemistry , enantioselective synthesis , molecule , botany , biology
Abstract An efficient metal‐free organocatalytic activation of hydrogen peroxide (H 2 O 2 ) 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.