Corey House Reaction

Corey's synthesis, the Wurtz reaction, the reduction of alcohols and aldehydes, Kolbe's electrolysis, the hydrogenation of alkenes, and the Grignard reaction are a few techniques for creating alkanes. Among the techniques available, the traditional Corey house reaction involves significant benefits in that it can produce symmetric, unsymmetrical, straight-chain, and branched-chain alkanes.

Additionally, utilizing primary alkyl halide with a variety of lithium dialkyl copper, spanning from primary to tertiary, enables the production of large yields of alkanes. The idea and workings of Corey house reactions can be utilized for so many different things. Additional studies were conducted to further enhance this synthetic method, opening the door to the production of several organic molecules that might be used as medicines to treat a wide range of illnesses. So this article provides deep knowledge on the concept of Corey house reaction with certain examples and mechanisms.

What is Corey House Reaction?

In order to create larger alkanes, 2 alkyl groups can be joined by the coupling mechanism. This flexible strategy is known as the Corey-House reaction.

Nevertheless, this reaction seldom functions effectively in practice because of metal-halogen exchanges and the creation of significant quantities of by-products from elimination or reduction separate from the employment of metal acetylides as nucleophiles. The Corey-House reaction provides a generic and very efficient mechanism for connecting two alkyl groups or an alkyl group and an aryl group in order to address this issue.

Mechanism of Corey House Reaction

The mechanism of Corey house reaction is explained through the following example:

\[{R_2}CuLi + R'X \to RR' + RCu + LiX\]

There are two steps in this reaction above. In order to create an alkyl lithium compound, R-Li, the alkyl halide is reacted with lithium metal and solvated in dry ether.

Primary, secondary, or tertiary alkyl halides can be the beginning R-X:

\[RX + 2Li \to RLi + LiX\]

Alkyl-lithium and cuprous iodide (CuI) are combined in the second stage to create lithium dialkyl cuprate. Gilman Reagents are the name for the main product of this reaction. Identical to Grignard and organolithium reagents, Gilman reagents are a resource of nucleophiles with carbanion-like properties. By using the Corey-House reaction, the Gilman reagent interacts with organic halides to convert the halide group into an R group, enabling the production of complex compounds from basic constituents.

\[2RLi + CuI \to {R_2}CuLi + LiI\]

The second alkyl halide is then utilized to convert the lithium dialkyl cuprate that couples to the compound:

\[{R_2}CuLi + R'X \to RR' + RCu + LiX\]

Cross-products develop if the second alkyl halide differs from the initial. It is crucial to remember that the second alkyl halide needs to be a methyl halide, benzyl halide, primary alkyl halide, or secondary cyclo alkyl halide for the mechanism to be effective. This mechanism is important for synthesising organic molecules because of how straightforward it is.

Example of Corey House Reaction

The Corey house reaction example is provided below:

\[{\left( {C{H_3}} \right)_2}CuLi + C{H_3}C{H_2}Br \to C{H_3}C{H_2}C{H_3} + C{H_3}Cu + LiBr\]

In the environment of dry ether, lithium dimethyl cuprate combines with ethyl bromide to produce propane together with lithium bromide and methyl copper.

As a result of the reaction between methyl bromide (an alkyl halide) and lithium metal in the environment of dry ether, methyl lithium and lithium bromide are produced. In order to create lithium dimethyl cuprate, or Gilman reagent, methyl lithium is first reacted using cuprous iodide.

Advantages of Corey House Reaction over Wurtz Reaction

• Any kind of alkane, whether straight chained or branching chain, with an even or odd number of carbon atoms, can indeed be synthesised utilizing the Corey-House reaction. The primary usage of this reaction is the production of higher alkanes. This reaction is thus more appropriate than the Wurtz reaction.

• Whenever primary alkyl halide and primary, secondary, or tertiary lithium dialkyl copper are employed, Corey house reaction can generate massive outputs of alkanes.

• The most effective and accessible method for synthesising complex organic compounds is the Corey-House reaction, which applies coupling pairs, functional group endurance, and simple procedure. Additionally, it works well at room temperature.

Interesting Facts

• The four organic chemists that collaborated to create this important Corey house reaction were Herbert O. House of the Georgia Institute of Technology, Gary H. Posner of Johns Hopkins University, G.M. Whitesides of MIT, and E.J. Corey of Harvard University.

• The alternative names for the Corey-House reaction include Corey-Posner, Whitesides-House reaction, and other permutations.

• These lithium dialkyl cuprate or organ copper compounds are frequently referred to as Gilman reagents in recognition of Henry Gilman, who created them.

Keywords to Remember Features

• Three steps make up the Corey-House reaction. Alkyl halide can be converted to alkyl lithium molecules by treating it with lithium metal, solvating it in dry ether, and then treating the alkyl lithium compound using cuprous halide to produce dialkyl lithium cuprate.

• The reagents employed in this synthesis are cuprous iodine and lithium metal. The substrates can be two alkyl halides that are identical or distinct. This process employs the coupling reaction as its mechanism. Lithium dialkyl cuprate and alkyl halide effectively couple, and the result is the production of hydrocarbons.

• Lithium dialkyl cuprate also couples with vinyl and phenyl halide.