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