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Increased Efficiency in Cross-Metathesis Reactions of Sterically Hindered Olefins

Ian C. Stewart, Christopher J. Douglas and Robert H. Grubbs*

*The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, Email:

I. C. Stewart, C. J. Douglas, R. H. Grubbs, Org. Lett., 2008, 10, 441-444.

DOI: 10.1021/ol702624n


Steric bulk of N-heterocyclic carbene ligands affects the efficiency in cross-metathesis reactions. 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.

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Key Words

Cross Metathesis

ID: J54-Y2008-0320