Synthesis of cyclobutane-fused chromanones <i>via</i> gold-mediated photocatalysis
Vladislav A. Voloshkin, Marco Villa, Ekaterina A. Martynova, Marek Beliš, Kristof Van Hecke, Paola Ceroni, Steven P. Nolan
Abstract
[2 + 2]-cycloaddition reactions. Herein, we present the use of [Au(SIPr)(Cbz)] as a sensitizer for the [2 + 2]-cycloaddition of coumarins and unactivated alkenes. Widely used in EnT catalysis, iridium and organic sensitizers proved less efficient under the examined catalytic conditions. The developed protocol permits the synthesis of cyclobutane-fused chromanones from readily available starting materials. A wide range of alkenes and substituted coumarins, including naturally occurring compounds, were reacted under mild conditions leading to structurally complex products with good functional group tolerance. Mechanistic studies reveal a previously overlooked reaction pathway for energy transfer catalysis involving coumarins.