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Published February 7, 2008 | Supplemental Material
Journal Article Open

Increased Efficiency in Cross-Metathesis Reactions of Sterically Hindered Olefins


Efficiency in olefin cross-metathesis reactions is affected upon reducing the steric bulk of N-heterocyclic carbene ligands of ruthenium-based catalysts. For the formation of disubstituted olefins containing one or more allylic substituents, the catalyst bearing N-tolyl groups is more efficient than the corresponding N-mesityl catalyst. In contrast, the formation of trisubstituted olefins is more efficient using the N-mesityl-containing catalyst. A hypothesis to explain this dichotomy is described.

Additional Information

© 2008 American Chemical Society. Received 29 October 2007. Published online 5 January 2008. Published in print 1 February 2008. The authors thank the NIH (postdoctoral fellowships to I.C.S. and C.J.D. and Grant 5RO1GM-31332 to R.H.G.), Dr. Patricio Romero (Caltech) for helpful discussions, and Materia Inc. for their generous donation of catalysts used in these studies.

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