CoreyHouse synthesis

The CoreyHouse synthesis (also called the Corey

Posner, WhitesidesHouse reaction and other permutations) is an organic reaction that involves the reaction
of a lithium dialkyl cuprate with an alkyl halide to form
a new alkane, an organocopper compound and a lithium
halide.[1][2][3]

E.J. Corey of Harvard University, former mentor of Gary

H. Posner of the Johns Hopkins University, as well as
George M. Whitesides of Harvard (then at MIT), former
mentor of Herbert O. House of the Georgia Institute of
Technology.

3 See also

R2 CuLi + R'-X R-R' + RCu + LiX

Gilman reagent

Reaction mechanism

Wurtz reaction

This reaction occurs in two steps. The alkyl halide is

treated with lithium metal, and solvated in dry 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:

4 References
[1] Posner, G. H. (1975). Substitution Reactions using
Organo Copper Reagents. Organic Reactions 22. p. 253.
doi:10.1002/0471264180.or022.02.

R-X + 2Li R-Li + Li-X

[2] Corey, Elias J.; Posner, Gary H. (19 July 1967). Selective formation of carbon-carbon bonds between unlike groups using organocopper reagents. Journal of
the American Chemical Society 89 (15): 39113912.
doi:10.1021/ja00991a049.

The second step requires the alkyl lithium compound

to be treated with cuprous iodide (CuI). This creates a
lithium dialkyl cuprate compound. These compounds
were rst synthesized by Henry Gilman of Iowa State
University, and are usually called Gilman reagents in
honor of his contributions:

[3] House, Herbert O.; Respess, William L.; Whitesides,

George M. (1 October 1966). The Chemistry of
Carbanions. XII. The Role of Copper in the Conjugate Addition of Organometallic Reagents. The
Journal of Organic Chemistry 31 (10): 31283141.
doi:10.1021/jo01348a012.

2RLi + CuI R2 CuLi + LiI

The lithium dialkyl cuprate is then treated with the second
alkyl halide, which couples to the compound:
R2 CuLi + R'-X R-R' + RCu + LiX
If second alkyl halide is not the same as the rst, then
cross-products are formed.
It is important to note that for this reaction to work successfully, the second 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:
1

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