Addition of organocuprates (Gilman reagents) to acid chlorides to give ketones

Description: Addition of organocuprates (Gilman reagents) to acid chlorides results in ketones.
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Notes:

• Note that organocuprates only add once to acid chlorides, whereas Grignard and organolithium reagents will add twice.
• Also note that organocuprates do not add to ketones.
• Although not shown, this also works for acid bromides

Examples:

Notes: Note that the byproduct of all of these reactions is the “organocopper” reagent, RCu and lithium chloride (LiCl)

Mechanism: The reaction proceeds through 1,2-addition of a carbon from the Gilman reagent to the carbonyl carbon (Step 1, arrows A and B) followed by 1,2-elimination of chloride ion (Step 2, arrows C and D) to give the ketone.

Notes: Again, note that organocuprates will not add twice to ketones, which distinguishes them from Grignard reagents and organolithium reagents.

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