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Published February 25, 2008 | Accepted Version
Journal Article Open

Kinetic Selectivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes


The evaluation of ruthenium olefin metathesis catalysts 4–6 bearing cyclic (alkyl)(amino)carbenes (CAACs) in the cross-metathesis of cis-1,4-diacetoxy-2-butene (7) with allylbenzene (8) and the ethenolysis of methyl oleate (11) is reported. Relative to most NHC-substituted complexes, CAAC-substituted catalysts exhibit lower E/Z ratios (3:1 at 70% conversion) in the cross-metathesis of 7 and 8. Additionally, complexes 4–6 demonstrate good selectivity for the formation of terminal olefins versus internal olefins in the ethenolysis of 11. Indeed, complex 6 achieved 35 000 TONs, the highest recorded to date. CAAC-substituted complexes exhibit markedly different kinetic selectivity than most NHC-substituted complexes.

Additional Information

© 2008 American Chemical Society. Received August 6, 2007. D.R.A. acknowledges NSF and NDSEG predoctoral fellowships. G.M., T.U., and Y.S. thank the DOE (DE-FG36-04GO14016) and Cargill, Inc. for financial support. R.H.G. is grateful to the NSF for funding (CHE-0410425). G.B. thanks the NIH for financial support (R01 GM 68825).

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