The Corey House Reaction is a useful method in organic chemistry to make new carbon-carbon bonds. It was discovered by two scientists, E.J. Corey and A. House, and is named after them.

This reaction helps chemists join two different hydrocarbon parts together using special compounds called Gilman reagents. It’s especially helpful in creating larger organic molecules from simpler ones. In this topic, you’ll learn what the Corey House reaction is, how it works, and why it’s important in making complex compounds in labs and industries.

What is Corey House Reaction?

The organic synthesis used for yielding alkanes by reacting lithium dialkyl cuprate (R2CuLi), with an organic alkyl halide (R′X) along with organocopper species and lithium halide as side product is known as Corey House Reaction. Generally the chemical reaction can be given as-

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Let us see an example of Corey House Reaction-

In the above example, a stepwise reaction of Ethyl chloride is shown. Ethyl chloride undergoes Corey House Reaction to yield n-Butane as the required product along with lithium chloride and ethyl cuprate as side products.

The reagents used in this reaction are lithium diethyl cuprate C2H5CuLi, organic pseudohalide (R′X) and ether.

The reaction proceeds with alkyl halides reacting with lithium in the presence of dry ether to give alkyl lithium.

R-X+2 \mathrm{Li} \rightarrow R-\mathrm{Li}+\mathrm{Li} X

In the second step, the alkyl lithium formed reacts with copper iodide to give lithium dialkyl cuprate (dialkyl lithium cuprate), also known as Gilman’s Reagent and lithium iodide.

In the last step, lithium dialkyl cuprate reacts with alkyl halide to yield the required alkane with organocopper and lithium halide as side products.

\mathrm{Li} R_2 \mathrm{Cu}+R^{\prime}-X \rightarrow R-R^{\prime}+R-\mathrm{Cu}+\mathrm{Li} X

Synthesis of Gilman Reagents

Gilman reagents are special chemicals used in organic chemistry to join two carbon groups together. Their chemical formula is R2CuLi, where R stands for an alkyl group (like a part of a carbon chain). They’re very useful in making larger organic molecules, especially during the Corey- House reaction.

Preparation of Gilman Reagents

Gilman reagents are made in two easy steps:

Step 1: formation of Alkyl Lithium

Take an alkyl halide (R-X) and react it with lithium metal (Li) in dry ether.

This gives you alkyl lithium (R-Li)

\mathrm{R}-\mathrm{X}+2 \mathrm{Li} \rightarrow \mathrm{R}-\mathrm{Li}+\mathrm{LiX}

Step 2: reaction with Copper(I) Iodide

Now, react alkyl lithium with copper(I) iodide (Cul)

This forms the Gilman reagent (R2CuLi) and Lithium iodide (Lil)

Application and Uses of Corey House Reaction

Following are the uses of Corey House Reaction.

• The reaction is a great alternative to the Wurtz reaction for the preparation of alkanes because of its high yield.
• The reaction can be used to make symmetrical, unsymmetrical and straight-chained or branched-chain alkanes.

Limitations of the Corey House Reaction

• Works best with primary alkyl halides
• Secondary and tertiary halides often give unwanted side reactions
• Aryl and vinyl halides usually do not react
• Bulky or sensitive substrates reduce efficiency or selectivity

Difference Between Corey House and Related Reaction

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