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A stereospecific route to olefins through sequential coupling reaction of Grignard reagents with 1-bromo-2-phenylthioethene in the presence of nickel or palladium catalysts
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1982
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Chemical EngineeringCross-coupling ReactionEngineeringAlkene MetathesisGrignard ReagentsAliphatic Grignard ReagentsOrganic ChemistryPalladium CatalystsCatalysisStereospecific RouteChemistryR1–chch–r2 TypeC–c BondsOrganometallic CatalysisAsymmetric CatalysisEnantioselective SynthesisBiomolecular Engineering
The room temperature sequential formation of two C–C bonds by reaction of aromatic or aliphatic Grignard reagents with (E)- or (Z)-1-bromo-2-phenylthioethene in the presence of nickel(II) or palladium(II) catalysts provides a novel stereospecific route to a variety of (E)- or (Z)-olefins of the R–CHCH–R and R1–CHCH–R2 type, with a stereoselectivity higher than 99% for the (E) isomers and in the range 95–98% or the (Z) isomers.