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Catalyst-free photoredox addition–cyclisations: exploitation of natural synergy between aryl acetic acids and maleimide

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Author(s)

John Christopher Walton, David W. Manley, Andrew Mills, Christopher O'Rourke, Alexandra Martha Zoya Slawin

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Abstract

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 a radical generating photoxidant and as a radical acceptor, negating the need for an extrinsic photoredox catalyst. Modest to excellent yields of the product chromenopyrroledione, thiochromenopyrroledione and pyrroloquinolinedione derivatives were obtained in thirteen preparative photolyses. In situ NMR spectroscopy was used to study each reaction. Reactant decay and product build-up were monitored, enabling reaction profiles to be plotted. A plausible mechanism, whereby photo-excited maleimide acts as an oxidant to generate a radical ion pair, has been postulated and is supported by UV/Vis. spectroscopy and DFT computations. The radical-cation reactive intermediates were also characterised in solution by EPR spectroscopy.
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Original languageEnglish
JournalChemistry - A European Journal
Volume20
DOIs
StatePublished - 20 Mar 2014

    Research areas

  • EPR spectroscopy , Heterocyclic compound, NMR spectroscopy , Photochemistry, Radicals

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