Highly Selective Synthesis of 2-<i>tert</i>-Butoxy-1-Arylethanones via Copper(I)-Catalyzed Oxidation/<i>tert</i>-Butoxylation of Aryl Olefins with TBHP
Jiantao Zhang, Duoduo Xiao, Hua Tan, Weibing Liu
Abstract
A practical and environmentally friendly protocol for the selective oxidation of aryl olefins to arylethanone derivatives by using a Cu(I) catalyst and tert-butyl hydroperoxide (TBHP) has been developed. A series of 2-tert-butoxy-1-arylethanones were obtained in moderate to good yields under mild conditions with high selectivity. In this method, TBHP acts not only as an oxidant but also as the tert-butoxy and carbonyl oxygen sources. This enables one-step oxidation/tert-butoxylation. Various allyl peroxides were also synthesized from allyl substrates.
Topics & Concepts
ChemistryCatalysisSelectivityAryltert-Butyl hydroperoxideCopperOrganic chemistryMolecular oxygenOxygenEnvironmentally friendlyCombinatorial chemistryMedicinal chemistryAlkylEcologyBiologyOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions