Generation of Stoichiometric Ethylene and Isotopic Derivatives and Application in Transition Metal-Catalyzed Vinylation and Enyne Metathesis

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  • Geanna Min, Denmark
  • Klaus Meier Bjerglund, Denmark
  • Søren Kramer, Denmark
  • Thomas Gøgsig, Denmark
  • Anders Thyboe Lindhardt, Denmark
  • Troels Skrydstrup
Ethylene is one of the most important building blocks in industry for the production of polymers and commodity chemicals. 13C- and D-isotope-labeled ethylenes are also valuable reagents with applications ranging from polymer-structure determination, reaction-mechanism elucidation to the preparation of more complex isotopically labeled compounds. However, these isotopic derivatives are expensive, and are flammable gases, which are difficult to handle. We have developed a method for the controlled generation of ethylene and its isotopic variants including, for the first time, fully isotopically labeled ethylene, from simple alkene precursors by using Ru catalysis. Applying a two-chamber reactor allows both the synthesis of ethylene and its immediate consumption in a chemical transformation permitting reactions to be performed with only stoichiometric amounts of this two carbon olefin. This was demonstrated in the Ni-catalyzed Heck reaction with aryl triflates and benzyl chlorides, as well as Ru-mediated enyne metathesis.
Original languageEnglish
JournalChemistry: A European Journal
Volume19
Issue51
Pages (from-to)17603–17607
ISSN0947-6539
DOIs
Publication statusPublished - 16 Dec 2013

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