Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis |
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| Authors: | Dr. Vanessa M. Marx Alexandra H. Sullivan Dr. Mohand Melaimi Dr. Scott C. Virgil Dr. Benjamin K. Keitz Dr. David S. Weinberger Prof. Guy Bertrand Prof. Robert H. Grubbs |
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| Affiliation: | 1. Department of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA);2. UCSD‐CNRS Joint Research Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, San Diego, CA 92093 (USA);3. Center for Catalysis and Chemical Synthesis, California Institute of Technology, Pasadena, CA 91125 (USA) |
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| Abstract: | 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. |
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| Keywords: | cyclic alkyl amino carbenes ethenolysis olefin metathesis seed‐oil derivatives terminal olefins |
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