Hypervalent Iodine Mediated C–C Double Bond Activation: A Cascade Access to α-Keto Diacetates from Readily Available Cinnamic Acids

Abstract

The reaction of cinnamic acids with (diacetoxyiodo)benzene in 1,2-dichloroethane in the presence of sulfuric acid provides an easy and direct access to the α-keto diacetate framework. This hypervalent iodine mediated oxidative reaction involves a tandem sequence of aryl migration, insertion of an oxygen atom, decarboxylation and diacetoxylation. A reaction mechanism is proposed and discussed in light of control experiments.

Key words

hypervalent iodine reagents - C–C double bond activation - decarboxylation - aryl migration - α-keto diacetates

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