Corey House Synthesis: Definition, Mechanism, Importance, Examples

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Corey House synthesis

Corey House synthesis of alkanes involves the coupling of alkyl halides with organometallic compounds to produce higher alkanes. E.J. Corey and Herbert House developed this approach in the 1960s. As a result, it is frequently referred to as Corey House synthesis. It is a flexible approach for producing alkane.

Lithium dialkyl cuprate (R2CuLi), an organometallic compound, is utilized in this coupling. This reagent, also known as Gilman reagent, was developed for the first time by Herry Gilman.

Gilman reagent (R2CuLi) synthesis

Alkyl halide reacts with lithium in dry ether to from alkyl lithium.

RX + Li → RLi + LiX

The alkyl lithium reacts wih CuI to give dialkylmlithium cuprate known as Gilman reagent.

2 RLi + CuI → R2CuLi + Li I

Mechanism of Corey house synthesis

The dialkyl lithium cuprate reacts with alkyl halide to give higher alkane. This is known as Corey House synthesis.

R2CuLi + R’X → R-R’ + R-Cu + LiX

In this reaction R’ may be mehyl halide, primary alkyl halide, or secondary alkyl halide. The alkyl group in lithium dialkyl cuprate may be methyl, 1o , 2o , 3o . Additionally, it is not necessary for the two alkyl groups to be different.

Although the mechanism of Corey House’s alkane synthesis is unknown, it’s clear that the alkyl group R moved from the copper, taking a pair of electrons with it, and bonded to the alkyl group R’ in place of the halide ion. That substitution process is nucleophilic.

For example:

C2H5Cl + Li → C2H5Li

2 C2H5Li + CuI → 2C2H5– Cu Li + LiI

2C2H5– Cu Li + CH3Br → C2H5– CH3 + C2H5 – Cu + LiBr

Importance of Corey House synthesis

1. It is better method than Wurtz reaction. in this reaction alkyl halide reacts with lithium dialkyl cuprate to give higher hydrocarbon.

R2CuLi + R’X → R-R’ + R-Cu + LiX

2. The primary significance of this reaction is that it can be used to prepare symmetrical, asymmetrical (unsymmetrical), straight chain, and branched chain alkanes.

3. It is a powerful and practical tool for the synthesis of complex organic compounds.

References

  1. Smith M. & March J. (2001). March’s advanced organic chemistry : reactions mechanisms and structure (5th ed.). Wiley.
  2. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Alkanes/Synthesis_of_Alkanes/Corey-House_Reaction.
  3. https://www.vedantu.com/chemistry/corey-house-reaction.

About Author

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Kabita Sharma

Kabita Sharma is a Ph.D. student in the Department of Chemistry at the University of North Texas, USA. Her research focuses on understanding protein degradation mediated by PROTAC (Proteolysis-Targeting Chimera) molecules and on exploring their potential for targeted protein degradation to treat diseases such as cancer. Through this work, she aims to advance drug discovery by targeting previously inaccessible or undruggable sites where PROTAC molecules can operate effectively. Additionally, she is analyzing how the buried surface area of proteins affects their binding and unbinding affinities. Using computational tools, she explores the challenges of removing one infected protein from another during treatment. Driven by a passion for solving complex scientific challenges, Kabita uses her knowledge in chemistry, chemical biology, and computational tools to advance her research. Beyond her academic pursuits, she aspires to inspire others toward science and its wonders through writing and sharing her knowledge.

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