Visible-light-induced controllable transformations of cumulative aryldienes through an energy transfer process

Abstract

In this work, we report a visible light-induced energy transfer process related photochemical protocol of cumulative diene containing compounds for the construction of benzocyclohexene skeletons or the corresponding aromatized structures through an energy transfer process, 1,5-hydrogen atom transfer and a 6π electrocyclization or demethoxylation in the presence of different photocatalysts such as [Ir(dF(Me)ppy)₂(dtbbpy)]PF₆ or thioxanthone. This newly developed photochemical strategy is characterized by mild conditions, broad substrate applicability, good functional group tolerance and good yields. The mechanistic paradigm was clarified by deuterium labeling, kinetic, photophysical and electrochemical analyses, control experiments and density functional theory (DFT) calculations. The transformation of the obtained product to the drug-like molecules such as Sertraline and the luminescent conjugated aromatic compounds has also been disclosed.