Cross Metathesis Reaction of Hindered Substrates

By: William Sommer, Aldrich ChemFiles 2009, 9.6, 7.

Aldrich ChemFiles 2009, 9.6, 7.

Exploiting the ability of the o-tolyl-NHC Hoveyda-Grubbs catalyst to react with hindered substrates, the Grubbs group recently reported a series of cross metathesis reactions between terminal olefins.1 Reduction in steric bulk contained on the NHC ligand resulted in successful coupling of sterically-hindered substrates (Scheme 2). The authors reported that this catalyst outperformed the Hoveyda-Grubbs catalyst (2nd Generation) in all cases studied. A variety of disubstituted olefins were prepared in good yields using 5 mol % of the catalyst.

Scheme 2

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  1. Stewart, I. C. et al. Org. Lett. 2008, 10, 441.

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