Abstract
AbstractIn Chapter 3, a [4+2] benzannulation reaction of an alkyne with a biaryl Grignard reagent is described. The reaction of internal or terminal alkynes and phenyl Grignard reagent proceeded in the presence of catalytic amounts of an iron salt and a bipyridine-type ligand, with a dichloroalkane as an oxidant to give 9,10-disubstituted or 9-substituted phenanthrenes and congeners. The reaction proceeded under mild conditions and bromide, chloride, trimethylsilyl, trifluoromethyl, and olefinic groups were tolerated. Mechanistic investigations suggest that this reaction involves a 5-membered ferracycle formation via C–H bond activation.KeywordsIron catalysisC–H bond activationFused aromatic compoundsPhenanthrene derivativesAlkyne annulations
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