Corey-House synthesis

The Corey-House synthesis (also called the Corey-House-Posner-Whitesides reaction) is an organic reaction that involves the reaction of a lithium dialkyl cuprate with an alkyl halide to form a new alkane. Organic reactions are Chemical reactions involving Organic compounds The basic Organic chemistry reaction types are Addition reactions Elimination Lithium (ˈlɪθiəm is a Chemical element with the symbol Li and Atomic number 3 Cuprate - A compound containing copper and some other element(s especially oxygen ? ( Cuprate previously redirected to Copper oxide) From 1986 The haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of Chemical compounds consisting of Alkanes such as Methane Alkanes, also known as Paraffins are Chemical compounds that consist only of the elements Carbon (C and Hydrogen (H (i ^[1]

R₂CuLi + R'-X → R-R'

1 Reaction mechanism
2 Background
3 References
4 See also

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 alkyl lithium compound to be treated with cuprous iodide (CuI). An organolithium reagent is an Organometallic compound with a direct bond between a Carbon and a Lithium atom Copper(I iodide is the Chemical compound with the formula CuI it is also known as cuprous iodide. This creates a lithium dialkyl cuprate compound. These compounds were first synthesized by Henry Gilman of Iowa State University, and are usually called 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. Henry Gilman ( May 9, 1893, - November 7, 1986) was an American Organic chemist known as the father of Organometallic chemistry The Iowa State University of Science and Technology, more commonly known as Iowa State University (ISU is a public land-grant and space-grant university A Gilman reagent is a Lithium and Copper ( diorganocopper) Reagent compound R2CuLi where R is an Organic radical.

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: E.J. Corey of Harvard University, Gary H. Elias James Corey (born July 12, 1928) is an American organic chemist. Posner of the Johns Hopkins University, G.M. Whitesides of MIT and Herbert O. George Whitesides may refer to George M Whitesides, an American chemist George T House of the Georgia Institute of Technology. The Georgia Institute of Technology, commonly known as Georgia Tech, or Tech, is a public, Coeducational Research university in

References

^ Posner, G. H. "Substitution Reactions using Organo Copper Reagents" Organic Reactions 1975, 22, 253.

Contents

Reaction mechanism

Background

References

See also