(CH3)2CuLI removing Cl from benzene?!?!

[nyr201]

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Hey guys, I was just going through my reactions and wondered how this worked...I don't know which page of the road maps its from but basically its m-chloro-nitrobenzene how does the Cl get removed by the grignard i thought aryl halides and SP2 carbons, in general were unreactive. Thanks in advance

 

[txlonghorn]

Hey guys, I was just going through my reactions and wondered how this worked...I don't know which page of the road maps its from but basically its m-chloro-nitrobenzene how does the Cl get removed by the grignard i thought aryl halides and SP2 carbons, in general were unreactive. Thanks in advance

From what I remember, R2CuLi adds an R in 1,4 manner, so it could attack a benzene in the 4 position and kick out the leaving group. I might be wrong, so someone else chime in.

 

[nyr201]

From what I remember, R2CuLi adds an R in 1,4 manner, so it could attack a benzene in the 4 position and kick out the leaving group. I might be wrong, so someone else chime in.

I actually researched this and its supposedly nucleophilic aromatic substitution which is not on the dat so i wont worry just memorize this just in case lol and the R2CuLi is called a Gilman reagent it replaces halides (not F) with an alkyl however on the benzene it does it via NAS i think