Corey-Posner, Whitesides-House reaction

Another transition metal-catalyzed carbon-carbon bond-forming reaction we shall discuss is the Corey—Posner, Whitesides-House reaction. Using this reaction an alkyl halide can be coupled with the alkyl group from a lithium dialkyl cuprate reagent (often called a Gilman reagent). This reaction does not have a catalytic mechanism. 

G.3 THE COREY-POSNER, WHITESIDES-HOUSE REACTION USE OF LITHIUM DIALKYL CUPRATES (GILMAN REAGENTS) IN COUPLING REACTIONS... 

The Corey—Posner, Whitesides—House reaction involves the coupling of a hthium dialkyl-cuprate (called a Gilman reagent) with an alkyl, alkenyl, or aryl halide. The alkyl group of the lithium dialkylcuprate reagent may be primary, secondary, or tertiary. However, the halide with which the Gilman reagent couples must be a primary or cychc secondary alkyl halide if it is not alkenyl or aryl. 

All of the reagents in a Corey-Posner, Whitesides-House reaction are consumed stoichiometrically. The mechanism does not involve a catalyst, as in the other reactions of transition metals that we have studied. 

G.3 The Corey-Posner, Whitesides-House Reaction Use of Lithium Dialkyl Cuprates (Gilman Reagents) in Coupling Reactions... 

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