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Chapter 26: Q 5 (page 1055)

One step in the synthesis of the nonsteroidal anti-inflammatory drug rofecoxib (trade name Vioxx) involves Suzuki coupling of A and B. What product is formed in this reaction?

Short Answer

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Answer

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01

Rofecoxib

Rofecoxib is a non-steroidal anti-inflammatory drug produced by cross-coupling a vinyl bromide with an organoborane.

02

Suzuki Coupling

The cross-coupling reaction involving an alkyl or vinyl halide, commonly a bromide or chloride with an organoborane in the presence of a base catalyzed by palladium, is known as the Suzuki coupling reaction.

The Suzuki coupling of A and B would give the following product:

Suzuki Coupling

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Most popular questions from this chapter

Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.

Devise a synthesis of the given trans vinylborane, which can be used for bombykol synthesis (Figure 26.1). All of the carbon atoms in the vinylborane must come from acetylene, nonane-1,9-diol, and catecholborane.

Draw the product formed from the ring-closing metathesis of each compound. Then, devisea synthesis of each metathesis starting material using any of the following compounds: CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganicreagents.

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What product is formed when each alkene is treated with and Zn(Cu)?

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