Corey–House synthesis


Corey–House synthesis

The Corey–Posner, Whitesides–House synthesis (also called the Corey–Posner, Whitesides–House reaction) 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]

R2CuLi + R'-X → R-R' + RCu + LiX

Contents

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). 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.

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. Posner of the Johns Hopkins University, George M. Whitesides of Harvard, and Herbert O. House of the Georgia Institute of Technology.

See also

References

  1. ^ Posner, G. H. (1975). "Substitution Reactions using Organo Copper Reagents". Organic Reactions. 22. pp. 253. doi:10.1002/0471264180.or022.02. 

Wikimedia Foundation. 2010.

Look at other dictionaries:

  • 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. [Posner, G. H. Substitution Reactions… …   Wikipedia

  • Elias James Corey — E.J. Corey Born 12 July 1928 (1928 07 12) (age 83) Methuen, Massachusetts, USA …   Wikipedia

  • Cuprate — For cuprate superconductors, see High temperature superconductivity#Cuprates. The unit cell of high temperature cuprate superconductor BSCCO 2212 Cuprates (from Latin cuprum meaning copper) are chemical compounds containing copper anion. Cuprates …   Wikipedia

  • Organic reaction — Organic reactions are chemical reactions involving organic compounds.[1] The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions,… …   Wikipedia

  • Wurtz reaction — The Wurtz reaction, named after Charles Adolphe Wurtz, is a coupling reaction in organic chemistry, organometallic chemistry and recently inorganic main group polymers, whereby two alkyl halides are reacted with sodium to form a new carbon carbon …   Wikipedia

  • Réaction organique — Les réactions organiques sont des réactions chimiques impliquant des composés organiques[1]. Les principaux types de réactions organiques sont l élimination, l addition, la substitution, le réarrangement et les réactions d oxydoréduction… …   Wikipédia en Français

  • List of organic reactions — Well known reactions and reagents in organic chemistry include Contents: A B C D E F G H I J K L M N O P Q R S T U V W X Y Z    See also   Ext …   Wikipedia

  • Francis Crick — Infobox Scientist name = Francis Harry Compton Crick |225px image width = 225px caption = Francis Harry Compton Crick birth date = 8 June 1916 birth place = Weston Favell, Northamptonshire, England residence = UK, U.S. nationality = British death …   Wikipedia

  • Abiogenesis — Primordial soup redirects here. For the board game, see Primordial Soup (board game). Origin of life redirects here. For views on the origins of life outside the natural sciences, see Creation myth. Pre Cambrian stromatolites in the Siyeh… …   Wikipedia

  • List of Duke University people — This list of Duke University people includes alumni, faculty, presidents, and major philanthropists of Duke University, which includes three undergraduate and ten graduate schools. The undergraduate schools include Trinity College of Arts and… …   Wikipedia