Auto-Tandem Catalysis: PdII-Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane-1,3-diones

Claire J. C. Lamb, Bryan G. Nderitu, Gemma McMurdo, John M. Tobin, Filipe Vilela, Ai-Lan Lee

Research output: Contribution to journalArticle

10 Citations (Scopus)
30 Downloads (Pure)

Abstract

A Pd(II) catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a onepot procedure: dehydrogenation of 2,2-disubstituted cyclopentane-1,3-diones and the subsequent oxidative Heck coupling. This auto tandem catalytic reaction is applicable to both batch and continuous flow processes, with the latter being the first example of a tandem aerobic dehydrogenation/oxidative Heck in flow. In addition, a telescoped reaction involving enantioselective desymmetrisation of the all-C quaternary centre was successfully achieved.
Original languageEnglish
Pages (from-to)18282–18288
Number of pages7
JournalChemistry - A European Journal
Volume23
Issue number72
Early online date30 Nov 2017
DOIs
Publication statusPublished - 22 Dec 2017

Keywords

  • aerobic oxidation
  • oxidative Heck
  • palladium
  • auto-tandem catalysis
  • one-pot synthesis

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