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Chapter 26: Q 26. (page 1070)

Identify X, an intermediate that was converted to eletriptan (trade name Relpax), a drug used to treat migraines.

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01

Heck reaction

The reaction between an alkene and an alkyl halide group in the presence of a base and a catalyst (palladium) is known as the Heck reaction. In this reaction, an alkene is formed.

02

Mechanism of Heck reaction  

  • In the first step, the divalent palladium catalyst reacts with the alkyl halide (RX) to form an organo-palladium compound.
  • In the second step, the (R) group and palladium (Pd) from the organopalladium compound add to the C=C such that Pd bonds with the more substituted carbon.
  • In the third step, the elimination of hydrogen and palladium takes place. Then, by reductive elimination, the initial palladium catalyst is regenerated.
03

Products of the given reaction 

Compound X is shown hereunder.

Compound X

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Most popular questions from this chapter

Devise a synthesis of each compound from benzene. You may also use any organic compounds having four carbons or fewer, and any required inorganic reagents.

a.

b.

The reaction of cyclohexene with iodo-benzene under Heck conditions forms E, a coupling product with the new phenyl group on the allylic carbon, but none of the “expected” coupling product F with the phenyl group bonded directly to the carbon–carbon double bond.

a. Draw a stepwise mechanism that illustrates how E is formed.

b. Step [2] in Mechanism 26.2 proceeds with syn addition of Pd and R' to the double bond.What does the formation of E suggest about the stereochemistry of the elimination reaction depicted in Step [3] of Mechanism 26.2?

Suzuki coupling of aryl iodide A and vinyl borane B affords compound C, which is converted to D in the presence of aqueous acid. Identify compounds C and D and draw a stepwise mechanism for the conversion of C to D.

When certain cycloalkenes are used in metathesis reactions, ring-opening metathesis polymerization (ROMP) occurs to form a high molecular weight polymer, as shown with cyclopentene as the starting material. The reaction is driven to completion by relief of strain in the cycloalkene.

What products are formed by ring-opening metathesis polymerization of each alkene?

In addition to organic halides, alkyl tosylates (R'OTs, Section 9.13) also react with organocuprates ( R2CuLi) to form coupling products R-R'. When 2° alkyl tosylates are used as starting materials ( R2CHOTs), inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with (CH3)2CuLi.

a.

b.
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