Concerted proton-coupled electron transfer is a key mechanism of substrate activation in biological redox catalysis. However, its applications in organic synthesis remain largely unexplored. The development of a new catalytic protocol for ketyl-olefin coupling along with evidence to support concerted proton-coupled electron transfer being the operative mechanism of ketyl formation will be presented. Notably, reaction outcomes were correctly predicted by a simple thermodynamic formalism relating the oxidation potentials and pKa values of specific Br�nsted acid/reductant combinations to their capacity to act jointly as a formal hydrogen atom donor.

Catalytic ketyl-olefin cyclizations enabled by proton-coupled electron-transfer

248th National Meeting (2014)

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