Catalyst-Free Photoredox Addition-Cyclisations: Exploitation of Natural Synergy between Aryl Acetic Acids and Maleimide
作者： David W. Manley , Andrew Mills , Christopher O'Rourke , Alexandra M. Z. Slawin , John C. Walton
关键词: Nuclear magnetic resonance spectroscopy 、 Acceptor 、 Radical 、 Electron paramagnetic resonance 、 Chemistry 、 Maleimide 、 Radical ion 、 Aryl 、 Catalysis 、 Organic chemistry 、 Photochemistry
摘要: Suitably functionalised carboxylic acids undergo a previously unknown photoredox reaction when irradiated with UVA in the presence of maleimide. Maleimide was found to synergistically act as radical generating photoxi- dant and acceptor, negating need for an ex- trinsic catalyst. Modest excellent yields product chromenopyrroledione, thiochromenopyrroledione pyrroloquinolinedione derivatives were obtained thir- teen preparative photolyses. In situ NMR spectroscopy used study each reaction. Reactant decay build-up monitored, enabling profiles be plotted. A plausible mechanism, whereby photo-excited mal- eimide acts oxidant generate ion pair, has been postulated is supported by UV/Vis. DFT computations. The radical-cation reactive intermedi- ates also characterised solution EPR spectroscopy.
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