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Published February 2, 2015 | public
Journal Article Open

Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis


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 100 000 were achieved, at a catalyst loading of only 3 ppm. Remarkably, the most active catalyst system was able to achieve a TON of 340 000, at a catalyst loading of only 1 ppm. 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 α-olefins (LAOs) and other terminal-olefin products.

Additional Information

© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: November 5, 2014. Article first published online: 17 DEC 2014. Lawrence M. Henling is acknowledged for X-ray crystallography analysis. Dr. David VanderVelde is thanked for assistance with NMR experiments. Thay Ung, Dr. Daryl P. Allen, and Dr. Richard L. Pederson (Materia Inc.) are thanked for helpful discussions regarding initial experimentation and setup. This work was financially supported by the NIH (5R01GM031332, 7R01GM068825), the NSF (CHE-1212767), the DOE (DE-FG02-13ER16370), and NSERC (fellowship to VMM).

Attached Files

Supplemental Material - anie_201410797_sm_miscellaneous_information.pdf

Accepted Version - nihms699226.pdf


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August 20, 2023
August 20, 2023