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

Kyle T. Tarantino, Peng Liu, Robert R. Knowles

Research output: Contribution to journalArticlepeer-review

148 Scopus citations

Abstract

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 Brønsted acid/reductant combinations to their capacity to act jointly as a formal hydrogen atom donor.

Original languageEnglish (US)
Pages (from-to)10022-10025
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number27
DOIs
StatePublished - Jul 10 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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