Synthesis of Ferrocenyl Alkenes, Dienes, and Enynes via Samarium Diiodide Promoted Tandem Addition and Dehydration of Ferrocenyl Carbonyls with Halides
journal contributionposted on 25.04.2001, 00:00 by Shean-Jeng Jong, Jim-Min Fang
A practical method for preparation of ferrocenyl alkenes, dienes, and enynes from ferrocenyl carbonyls was explored. A one-pot operation using samarium diiodide to promote the condensation reactions of ferrocenecarboxaldehyde, acetylferrocene, benzoylferrocene, and butanoylferrocene with benzyl bromides, allyl bromide, propargyl bromide, and 1-bromo-3-chlorobutane gave the olefinic products in very high yields. The condensation reactions were also achieved by using catalytic amounts of SmI2 with magnesium to regenerate the divalent samarium reducing agent.
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Enynecondensation reactionsbromobromideagentdieneHalideferrocenylbenzoylferroceneenynepreparationAlkenebutanoylferroceneallylcarbonylSmIpropargylmethodmagnesiumSynthesiSamarium Diiodide Promoted Tandem AdditionalkeneolefinicsamariumbenzylferrocenecarboxaldehydediiodidebromidesCarbonylyieldDieneDehydrationFerrocenylacetylferrocenedivalent