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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

What ring-closing metathesis product is formed when each substrate is treated with Grubbs catalyst under high-dilution conditions?

a.

b.

c.

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.

a.

b.

Bi-aryls, compounds containing two aromatic rings joined by a C-C bond, can often be efficiently made by two different Suzuki couplings; that is, either aromatic ring can be used to form the organoborane needed for coupling. In some cases, however, only one route is possible. With this in mind, synthesize each of the following bi-aryls using benzene as the starting material for each aromatic ring. When more than one route is possible, draw both of them. You may use any required organic or inorganic reagents.

What reagents are needed to carry out transformations [1]–[3] in the synthesis of aldehyde A? A can be converted to the antitumor agent maytansine in several steps.

Draw the structure of the two products of molecular formulaC15H26O2 formed when M is treated with Grubbs catalyst under high-dilution conditions.
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