Potassium 2-isocyanoacetate: Quenching Reagent for Metathesis

By: Dr. Mark Redlich, Chemfiles Volume 10 Article 1

Diver and co-workers recently described an efficient metathesis clean-up procedure using potassium 2-isocyanoacetate,1 which addresses the challenges associated with removal of the ruthenium at the end of a metathesis reaction. Upon quenching with the polar isocyanide, a benzylidene insertion of the mesityl group occurs, thus destroying the catalyst and imparting increased polarity for easy removal (Scheme 7). Potassium 2-isocyanoacetate was successfully used to quench a range of metathesis reactions and the authors demonstrated it can be employed with various highly utilized Grubbs' complexes.

Scheme 7

Scheme 7: (705438)

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  1. Galan, B. R. et al. Org. Lett. 2007, 9, 1203.

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