Chemistry - A European Journal p. 17603 - 17607 (2013)
Update date:2022-08-05
Topics:
Min, Geanna K.
Bjerglund, Klaus
Kramer, Soren
Gogsig, Thomas M.
Lindhardt, Anders T.
Skrydstrup, Troels
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. Why more when less works! A method for the controlled generation of ethylene including the fully isotopically labeled derivative is described, as well as their use in three transition-metal-catalyzed reactions. Applying a two-chamber reactor, only stoichiometric amounts of ethylene are required, which allows the simple installment of deuterium and 13C in the product (see scheme).
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