An expanded family of ruthenium metathesis catalysts bearing cyclic alkyl amino carbene (CAAC) ligands is reported. These catalysts exhibited exceptional activity in the ethenolysis of the seed oil derivative methyl oleate. In many cases, TONs >100,000 were achieved, at only 3 ppm catalyst loading. Remarkably, the most active catalyst system was able to achieve a TON of 340,000, at only 1 ppm catalyst loading. 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 towards the industrial scale production of linear alpha-olefins (LAOs) and other terminal olefin products.

** Mr. 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.