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

Claire J C LambBryan G NderituGemma McMurdoJohn M TobinFilipe VilelaAi-Lan Lee
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2017)
A PdII catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a one-pot 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.
Keyphrases
  • electron transfer
  • minimally invasive
  • ionic liquid
  • highly efficient
  • carbon dioxide