Deconstructive reactions have attracted significant interest in organic chemistry because they offer the opportunity to target transformations of complex scaffolds that would not be achievable using traditional means. These reactions typically involve cleavage of carbon–carbon sigma bonds followed by functionalization of the resultant reactive sites. Our group was inspired by recent reports which realize the photoredox deconstruction of cyclic alcohols followed by functionalization with group-transfer reagents. However, such methods are limited by the reactivity of these prefunctionalized reagents and therefore can only be used for a relatively small number of transformations. We envisioned that a deconstructive olefination would be a powerful method for synthesis, because downstream diversification of deconstructed olefin products is not limited by the scope of group-transfer chemistry. A system merging photoredox catalysis with Cu(II)-mediated oxidation was found to be effective for transforming cyclic alcohols into terminal olefins with broad tolerance to ring size and functional group variation. Furthermore, the olefin products were shown to be useful substrates for obtaining complex heterocyclic products.

Deconstructive olefination of cyclic alcohols enabled by an oxidative C–C bond activation strategy

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