Journal
CHEMSUSCHEM
Volume 8, Issue 24, Pages 4139-4148Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201500784
Keywords
isocyanides; metathesis; olefins; ruthenium; scavengers
Funding
- Foundation for Polish Science
- Ventures program of the Foundation for Polish Science
- European Union Regional Development Fund
- European Union from the European Regional Development Fund
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Three isocyanides containing a tertiary nitrogen atom were investigated for use as small-molecule ruthenium scavenging agents in the workup of olefin metathesis reactions. The proposed compounds are odorless, easy to obtain, and highly effective in removing metal residues, sometimes bringing the metal content below 0.0015 ppm. The most successful of the tested compounds, II, performs very well, even with challenging polar products. The performance of these scavengers is compared and contrasted with other known techniques, such as silica gel filtration and the use of self-scavenging catalysts. As a result, a new hybrid purification method is devised, which gives better results than using either a self-scavenging catalyst or a scavenger alone. Additionally, isocyanide II is shown to be a deactivating (reaction quenching) agent for olefin metathesis and superior to ethyl vinyl ether.
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