Corey-House synthesis

Reaction mechanism

This reaction occurs in two steps. The alkyl halide is treated with lithium metal, and solvated in ether, which converts the alkyl halide into an alkyl lithium compound, R-Li. The starting R-X can be primary, secondary or tertiary alkyl halide:

R-X + 2Li → R-Li + Li-X

The second step requires the Gilman reagents in honor of his contributions:

2RLi + CuI → R₂CuLi + LiI

The lithium dialkyl cuprate is then treated with the second alkyl halide, which couples to the compound:

R₂CuLi + R'-X → R-R' + RCu + LiX

If second alkyl halide is not the same as the first, then cross-products are formed.

It is important to note that for this reaction to work successfully, the alkyl halide must be a methyl halide, benzyl halide, primary alkyl halide or a secondary cyclo alkyl halide. The relative simplicity of this reaction makes it a useful technique for synthesizing organic compounds.

Background

This reaction was developed by the co-operation of four organic chemists: G.M. Whitesides of MIT and Herbert O. House of the Georgia Institute of Technology.

References

See also

• Gilman reagent
• Wurtz reaction