lecture 24.1

lecture 24.1 - 24-24-1Organic Organic...

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Unformatted text preview: 24-24-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson24-24-2Carbon-Carbon Bond Carbon-Carbon Bond Formation and Formation and SynthesisSynthesisChapter 24Chapter 2424-24-3Organometallic CompoundsOrganometallic CompoundsFollowing are two extremely important reactions of metals and organometallic compoundsoxidative addition:oxidative addition:addition of a reagent to a metal center causing it to add two substituents and its oxidation to increase by tworeductive elimination:reductive elimination:elimination of two substituents at a metal center causing the oxidation state of the metal to decreased by twoMLn+ X2MLnoxidative additionreductiveeliminationXX24-24-4Heck ReactionHeck ReactionA palladium-catalyzed reaction in which the carbon group of a haloalkene or haloarene is substituted for a vinylic H of an alkeneR-XHBRBH+ X-+Pd catalyst++AlkeneBaseHaloalkeneor HaloareneConjugate acidof the baseSubstitutedalkeneHeck reaction24-24-5Heck ReactionHeck Reactionsubstitution is highly regioselective; most commonly at the less substituted carbon of the double bondsubstitution is highly stereoselective; where E,Zisomerism is possible in the product, the Econfiguration is often formed almost exclusivelyBrCH2=CHCOCH3OCOCH3O+BromobenzeneMethyl 2-propenoate(Methyl acrylate) Methyl (E)-3-phenyl-2-propenoate(Methyl cinnamate)Pd catalystHeck reaction24-24-6Heck ReactionHeck Reactionreaction is stereospecific with regard to the haloalkene; the configuration of the double bond in the haloalkene is preservedIPhPh(Z)-3-Iodo-3-hexene+(1E,3Z)-1-Phenyl-3-ethyl-1,3-hexadieneZZStyrenePd catalystHeck reactionIPhPh(E)-3-Iodo-3-hexene+(1E,3E)-1-Phenyl-3-ethyl-1,3-hexadieneEEStyrenePd catalystHeck reaction24-24-7Heck ReactionHeck ReactionThe catalystmost commonly Pd(II) acetatereduced in situ to Pd(0)reaction of Pd(0) with good ligands gives...
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This note was uploaded on 03/30/2008 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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lecture 24.1 - 24-24-1Organic Organic...

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