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Show how you would use a Suzuki reaction to synthesize the

Chapter 11, Problem 68SP

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QUESTION:

Show how you would use a Suzuki reaction to synthesize the following biaryl compound. As starting materials you may use the two indicated compounds, plus any additional reagents you need.

\(\mathrm{OCH}_{3}\)

\(B r\)

Equation transcription:

Text transcription:

{OCH}{3}

B r

Questions & Answers

QUESTION:

Show how you would use a Suzuki reaction to synthesize the following biaryl compound. As starting materials you may use the two indicated compounds, plus any additional reagents you need.

\(\mathrm{OCH}_{3}\)

\(B r\)

Equation transcription:

Text transcription:

{OCH}{3}

B r

ANSWER:

Solution:

Here we have to  synthesize the following biaryl compound by using Suzuki reaction .

Step 1

Suzuki reaction:-

The Suzuki reaction is also known as coupling reaction, in which the coupling partners are a boronic acid and an organohalide catalyzed by a palladium(0) complex.

    R1-BY2      +       R2X R1-R2  + BY2X

(boronic acid)  (organo halide)

Mechanism:-

The mechanism of the Suzuki reaction has been carried out in presence of base and palladium as a catalyst.

The first step is the oxidative addition of palladium to the halide 2 to form the organopalladium species 3. Reaction with base gives intermediate 4, which via transmetalation with the boron-ate complex 6 (produced by reaction of the boronic acid 5 with base) forms the organopalladium species 8. Reductive elimination of the desired product 9 restores the original palladium catalyst 1 which completes the catalytic cycle.

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