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J Am Chem Soc. 2013 Jul 10;135(27):10022-5. doi: 10.1021/ja404342j. Epub 2013 Jun 28.

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

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Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.


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. Herein, we report the development of a new catalytic protocol for ketyl-olefin coupling and present evidence to support concerted proton-coupled electron transfer being the operative mechanism of ketyl formation. Notably, reaction outcomes were correctly predicted by a simple thermodynamic formalism relating the oxidation potentials and pKa values of specific Br√łnsted acid/reductant combinations to their capacity to act jointly as a formal hydrogen atom donor.

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