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Magazine Chapter 26: Q 51. (page 1074)
Devise a synthesis of each of the following compounds. Besides inorganic reagents, you may use hydrocarbons and halides having C鈥檚, and as starting materials. Each synthesis must use at least one of the carbon鈥揷arbon bond-forming reactions in this chapter.
b.
c.
d.
Short Answer
Answer
a.
b.
c.
d.
Step by step solution
C-C coupling reactions with organometallic reagents
A C-C coupling reaction is a series of reactions where two different molecules fuse to give a new compound, and a C-C bond is formed between them.
A metal catalyst facilitates these reactions and the starting material is an organic halide.
There are several types of C-C coupling reactions.
- The reactions that involve an organocuprate reagent, also known as Gilman reagent. The starting material is an organic halide.
- The reaction that involves an organic halide, an organoboron reagent, and a palladium catalyst is known as the Suzuki reaction.
- Heck reaction involves the reaction of organic halides with an alkene in the presence of a palladium catalyst.
C-C coupling reaction synthesis using organocopper reagent
The following steps involve C-C coupling, and the starting material is compound.
a.
An organocopper reagent is employed to get the following product, as shown below:
Synthesis of compound a
b.
An organocopper reagent is used to form the desired product as given below:
Synthesis of compound b
C-C coupling reaction synthesis via Suzuki reaction
c.
The product is formed upon the treatment of the starting material with the organoboron reagent in the presence of a palladium catalyst.
Synthesis of compound c
C-C coupling reaction synthesis via Heck reaction
Bromo-benzene is made to react with in the presence of palladium acetate. The reaction is shown below:
Synthesis of compound d
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