Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 6, Pages 1919-1923Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201410797
Keywords
cyclic alkyl amino carbenes; ethenolysis; olefin metathesis; seed-oil derivatives; terminal olefins
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Funding
- NIH [5R01GM031332, 7R01GM068825]
- NSF [CHE-1212767]
- DOE [DE-FG02-13ER16370]
- NSERC
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1212767, 1502616] Funding Source: National Science Foundation
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An expanded family of ruthenium-based metathesis catalysts bearing cyclic alkyl amino carbene (CAAC) ligands was prepared. These catalysts exhibited exceptional activity in the ethenolysis of the seed-oil derivative methyl oleate. In many cases, catalyst turnover numbers (TONs) of more than 100000 were achieved, at a catalyst loading of only 3ppm. Remarkably, the most active catalyst system was able to achieve a TON of 340000, at a catalyst loading of only 1ppm. This is the first time a series of metathesis catalysts has exhibited such high performance in cross-metathesis reactions employing ethylene gas, with activities sufficient to render ethenolysis applicable to the industrial-scale production of linear -olefins (LAOs) and other terminal-olefin products.
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