SN2 reaction of organocuprates (Gilman reagents) with alkyl halides to give alkanes
Description: Alkyl halides (or tosylates) will react with organocuprates (Gilman reagents) to form alkanes in an SN2 reaction
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Notes: X here is a halide (Cl, Br, I) or sulfonate (OTs, OMs)
Also note that this can be a very useful way of forming carbon-carbon bonds.
Examples:
Notes: The byproduct of all of these reactions is the lithium salt (e.g. LiBr) and the organocopper species (e.g. CH3Cu).
Mechanism: This reaction is actually a fairly straightforward SN2 reaction, with breakage of the C–Cu bond accompanying attack at the alkyl halide (Step 1, arrows A and B).
Notes: Again note that this forms a carbon-carbon bond. This is important as there aren’t too many reactions that do so, through an SN2 (another example is the reaction of alkyl halides with acetylide ions).
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{ 3 comments… read them below or add one }
Hi, please for explaining how is created bond C1 and C2 in Mechanism? C1 is (+) and Cu is (-) —> C2 is (+) I suppose. Thx. P.
That is correct. C-2 attached to Cu is nucleophilic (partially negative) and C1 attached to Br is electrophilic (partially positive).
Oh, my mistake. Electronegativity (Cu) = 1,9 < Electronegativity (C) = 2,5. :-) Thx