Vanry
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organocopper coupling reaction ?
I was discussing organic chem with a friend, and we thought about using copper for gentle grignard-like coupling with things like this :
R-Br + Cu(metal) -> R-Cu-Br
R-Cu-Br + R'-Br -> R-R' + CuBr2
We were debating the feasability, and if this could be usefull to do some coupling between ketone (which is impossible with Mg-Br like reaction, that
would react with the ketone)
Does it seem viable to any of you ? I couldn't find anything in the library, and my OC teacher look at me this way and dodge the subject ![:D](./images/smilies/biggrin.gif)
thanks in advance
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Loptr
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Look into Gilman reagents. They are typically prepared from either Grignard and Alkyllithium reagents.
https://www.masterorganicchemistry.com/2016/01/29/gilman-rea...
[Edited on 21-9-2018 by Loptr]
"Question everything generally thought to be obvious." - Dieter Rams
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clearly_not_atara
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This technique is commonly used. However, the organocopper reagents are rarely prepared from organohalides and copper metal directly; instead, other
organometallic reagents, usually organolithium/organomagnesium/organozinc react with copper salts.
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unionised
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There's this...
https://en.wikipedia.org/wiki/Ullmann_reaction
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Vanry
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Very interesting ! Big thanks to all of you ! This sound like an amazing way to create C-C bond, might this be the OC holy grail ? ![:D](./images/smilies/biggrin.gif)
I was tempted to give it a go, before reading that This reagent must be prepared and handled around -70°c ! Someone to backup this info ? does anybody have a random procedure to prepare/use organocuprates ? (with things like
temperature, security concern...)
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Texium
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If you can get some dry ice, -70ºC is trivial with a dry ice/acetone bath.
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