2-Acyl imidazolyl groups can be used as 'redox auxiliaries' that can tune the reduction potential of a,ߖunsaturated carbonyl substrates such that they can participate in photocatalytic [2+2] cycloadditions with a variety of Michael acceptors. Methylation of the imidazolyl group of the cycloadduct enables the auxiliary to be readily cleaved by a variety of nucleophiles, generating functionalized cyclobutanes that are otherwise inaccessible via other methods.

Visible light–promoted [2+2] radical anion cycloadditions with cleavable redox auxiliaries

243rd National Meeting (2012)

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