Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones

Sebastian Armin Schwengers, Gabriela Guillermina Gerosa, Tynchtyk Amatov, Naoki Yasukawa, Sebastian Brunen, Markus Leutzsch, Benjamin Mitschke, Grigory André Shevchenko, Benjamin List

Research output: Contribution to journalArticlepeer-review

Abstract

We disclose a highly regioselective, catalytic one-step dehydrogenation of α-substituted cyclic ketones in the presence of 2,3-dichlorobenzo-5,6-dicyano-1,4-benzoquinone (DDQ). The high regioselectivity originates from a phosphoric acid-catalyzed enolization, selectively affording the thermodynamically preferred enol, followed by the subsequent oxidation event. Our method provides reliable access to several α-aryl and α-alkyl substituted α,β-unsaturated ketones.

Original languageEnglish (US)
Article numbere202307081
JournalAngewandte Chemie - International Edition
Volume62
Issue number35
DOIs
StatePublished - Aug 28 2023

Keywords

  • DDQ
  • Enol-Catalysis
  • Oxidations
  • Phosphoric Acids
  • α,β-Unsaturated Ketones

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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