Visible-Light-Activated Divergent Reactivity of Dienones: Dimerization in Neat Conditions and Regioselective E to Z Isomerization in the Solvent

Organic Letters
Sandip NaskarIndrajit Das

Abstract

2,4-Dienones undergo visible-light-promoted, photocatalyst-free dimerization in neat conditions to provide cyclohexene derivatives stereoselectively through cascade rearrangement pathways, whereas regioselective E → Z isomerization of the more dienophilic double bond takes place exclusively in nitromethane. On the basis of intermediate isolation and computational DFT studies, the dimerization reaction is proposed to proceed via s-trans to s-cis isomerization/regioselective E → Z isomerization/Diels-Alder cycloaddition.

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Citations

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