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Superelectrophilic Fe(III)-Ion Pairs as Stronger Lewis Acid Catalysts for (E)-Selective Intermolecular Carbonyl-Olefin Metathesis.

Haley AlbrightHannah L VoneshCorinna S Schindler
Published in: Organic letters (2020)
An intermolecular carbonyl-olefin metathesis reaction is described that relies on superelectrophilic Fe(III)-based ion pairs as stronger Lewis acid catalysts. This new catalytic system enables selective access to (E)-olefins as carbonyl-olefin metathesis products. Mechanistic investigations suggest the regioselective formation and stereospecific fragmentation of intermediate oxetanes to be the origin of this selectivity. The optimized conditions are general for a variety of aryl aldehydes and trisubstituted olefins and are demonstrated for 28 examples in up to 64% overall yield.
Keyphrases
  • metal organic framework
  • highly efficient
  • transition metal
  • energy transfer