Increased efficiency in cross-metathesis reactions of sterically hindered olefins |
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Authors: | Stewart Ian C Douglas Christopher J Grubbs Robert H |
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Institution: | The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA. |
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Abstract: | 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. |
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