Chapter 24

Chapter 24 - CHEM 262 Wei You Chapter 24. Carbon-Carbon...

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11 CHEM 262 Wei You Chapter 24. Carbon-Carbon Bond Formation
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04/28/2010 Wed Final Review session and Course Evaluation ( bring No.2 pencil ) 04/30/2010 Thurs More practice problems 05/03/2010 Mon Answer key uploaded 05/05/2008 Wed Office hour 4pm to 6pm Kenan B528 Final: May 7 , 2010 4pm to 6pm
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33 What We Learned Before 1. Sn2 reaction 1. Carbonyl 1. D-A
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44 Organometallic Compounds Following are two extremely important reactions of metals and organometallic compounds oxidative addition: addition of a reagent to a metal center causing it to add two substituents and its oxidation to increase by two reductive elimination: elimination of two substituents at a metal center causing the oxidation state of the metal to decreased by two ML n + X 2 ML n oxidative  addition reductive elimination X X
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55 Example 1: Heck Reaction Heck Reaction: A palladium-catalyzed reaction in which the carbon group of a haloalkene or haloarene is substituted for a vinylic H of an alkene R-X H B R BH +  X - + Pd catalyst + + Alkene Base Haloalkene or Haloarene Conjugate acid of the base Substituted alkene Heck reaction
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66 Heck Reaction substitution is highly regioselective ; most commonly at the less substituted carbon of the double bond substitution is highly stereoselective ; where E , Z isomerism is possible in the product, the E configuration is often formed almost exclusively Br CH 2 =CHCOCH 3 O COCH 3 O + Bromobenzene Methyl 2-propenoate (Methyl acrylate)   Methyl ( E )-3-phenyl-2-propenoate (Methyl cinnamate) Pd catalyst Heck reaction
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77 Heck Reaction reaction is stereospecific with regard to the haloalkene; the configuration of the double bond in the haloalkene is preserved I Ph Ph ( Z )-3-Iodo-3- hexene + (1 E ,3 Z )-1-Phenyl-3- ethyl-1,3-hexadiene Z Z Styrene Pd catalyst Heck reaction I Ph Ph ( E )-3-Iodo-3- hexene + (1 E ,3 E )-1-Phenyl-3- ethyl-1,3-hexadiene E E Styrene Pd catalyst Heck reaction
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88 Heck Reaction The catalyst most commonly Pd(II) acetate
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This note was uploaded on 06/12/2010 for the course CHEM 261 taught by Professor Austell during the Spring '08 term at UNC.

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Chapter 24 - CHEM 262 Wei You Chapter 24. Carbon-Carbon...

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