title: Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis.
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.
authors.affiliation: Department of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA).
authors.forename: Vanessa M
authors.initials: VM
authors.lastname: Marx
authors.forename: Alexandra H
authors.initials: AH
authors.lastname: Sullivan
authors.forename: Mohand
authors.initials: M
authors.lastname: Melaimi
authors.forename: Scott C
authors.initials: SC
authors.lastname: Virgil
authors.forename: Benjamin K
authors.initials: BK
authors.lastname: Keitz
authors.forename: David S
authors.initials: DS
authors.lastname: Weinberger
authors.forename: Guy
authors.initials: G
authors.lastname: Bertrand
authors.forename: Robert H
authors.initials: RH
authors.lastname: Grubbs
mesh_terms: D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D012428:Ruthenium / Q000737:chemistry*
chemical_list: D005030:Ethylenes; C030011:carbene; D012428:Ruthenium; C036216:ethylene; D008697:Methane
keywords: cyclic alkyl amino carbenes; ethenolysis; olefin metathesis; seed-oil derivatives; terminal olefins