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Chapter 24: Problem 6

What sequence of reactions will produce the following product if starting with trimethylsilyl acetylene and the appropriate two aryl iodides?

Short Answer

Expert verified
Answer: The sequence of reactions involves two Sonogashira reactions. First, perform a Sonogashira reaction between trimethylsilyl acetylene and the first aryl iodide, yielding an intermediate with one aryl group attached to the alkyne. Then, perform a Sonogashira reaction between the intermediate and the second aryl iodide, yielding the final product with both aryl groups attached to the alkyne.

Step by step solution

01

Identify the desired product and the starting material

First, we need to determine what the desired product is from the question and identify our starting material. In this case, the starting material is trimethylsilyl acetylene, which has the formula \((\text{CH}_3)_3\text{SiC}\equiv\text{CH}\). We are also given two aryl iodides as reactants. An aryl iodide is an iodine-substituted aromatic ring, which can be represented by the general formula Ar-I, where Ar is an aromatic ring and I is an iodine atom.
02

Analyze the possible reactions that involve the given starting material and aryl iodides

There are many possible reactions that involve aryl iodides, but the most common one that would involve trimethylsilyl acetylene is the Sonogashira reaction. The Sonogashira reaction is a cross-coupling reaction between an aryl or vinyl halide and an alkyne, catalyzed by a palladium(0) complex and a copper(I) salt. The general reaction proceeds as follows: \(Ar-X + R'\text{C} \equiv \text{CH} \rightarrow Ar\text{C} \equiv \text{CH}R'\), where \(Ar\) is an aromatic ring, \(X\) is a halide, and \(R'\) is the other alkyne substituent.
03

Propose a sequence of reactions for the given starting material and aryl iodides

Our starting material is trimethylsilyl acetylene, and we have two aryl iodides to incorporate into our product. Therefore, we will need to perform two Sonogashira reactions sequentially to obtain the desired product. First, we will react trimethylsilyl acetylene with one of the aryl iodides using Sonogashira coupling conditions (Pd(0) catalyst and Cu(I) salt). This will give us an intermediate that contains one of the aryl groups attached to the alkyne. Then, we will react this intermediate with the second aryl iodide, again using Sonogashira coupling conditions, to give us the final product with both aryl groups attached to the alkyne.
04

Summary of steps to produce the desired product

1. Perform a Sonogashira reaction between trimethylsilyl acetylene and the first aryl iodide using Pd(0) catalyst and Cu(I) salt, yielding an intermediate with one aryl group attached to the alkyne. 2. Perform a Sonogashira reaction between the intermediate formed in step 1 and the second aryl iodide using Pd(0) catalyst and Cu(I) salt, yielding the final product with both aryl groups attached to the alkyne.

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Most popular questions from this chapter

When the \(\mathrm{Pd}(0)\)-catalyzed reactions covered in this chapter are run with a slight pressure of carbon monoxide, it is often found that a ketone is created as the product. For example, the following Stille coupling conditions with added CO give the product shown. Write a mechanism for how this reaction could occur using the organometallic mechanistic steps introduced in this chapter, along with new steps that would be required in this transformation.

Show the sequence of Heck reactions by which the following conversion takes place. Note from the molecular formula given under each structural formula that this conversion corresponds to a loss of \(\mathrm{H}\) and I from the starting material.

Treatment of cyclohexene with iodobenzene under the conditions of the Heck reaction might be expected to give 1-phenylcyclohexene. The exclusive product, however, is 3-phenylcyclohexene. Account for the formation of this product.

Show how you might prepare each compound by a Heck reaction using methyl 2-propenoate as the starting alkene.

The aryl diene undergoes sequential Heck reactions to give a product with the molecular formula \(\mathrm{C}_{15} \mathrm{H}_{18}\). Propose a structural formula for this product.
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