Highly Z-Selective Metathesis Homocoupling of Terminal Olefins
Journal of the American Chemical Society2009Vol. 131(46), pp. 16630–16631
Citations Over TimeTop 10% of 2009 papers
Abstract
Mo and W MonoAryloxide-Pyrrolide (MAP) olefin metathesis catalysts can couple terminal olefins to give as high as >98% Z-products in moderate to high yields with as little as 0.2% catalyst. Results are reported for 1-hexene, 1-octene, allylbenzene, allyltrimethylsilane, methyl-10-undecenoate, methyl-9-decenoate, allylB(pinacolate), allylOBenzyl, allylNHTosyl, and allylNHPh. It is proposed that high Z-selectivity is achieved because a large aryloxide only allows metallacyclobutanes to form that contain adjacent cis substituents and because isomerization of Z-product to E-product can be slow in that same steric environment.
Related Papers
- → Synthesis of Z-Alkenes from Rh(I)-Catalyzed Olefin Isomerization of β,γ-Unsaturated Ketones(2013)79 cited
- → Cation-Controlled Olefin Isomerization Catalysis with Palladium Pincer Complexes(2022)13 cited
- → Ligand donor atom and substituent effects in olefin oligomerization and isomerization catalysed by nickel-based catalyst systems(1992)17 cited
- → Effect of ligand donor-acceptor properties on selectivity of catalytic olefin isomerization reaction(1995)7 cited
- → Mastering mono-bond metathesis(2021)