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Author: Subject: organocopper coupling reaction ?
Vanry
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[*] posted on 21-9-2018 at 05:11
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 :o and dodge the subject :D

thanks in advance

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Loptr
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[*] posted on 21-9-2018 at 06:11



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]




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clearly_not_atara
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[*] posted on 21-9-2018 at 08:24


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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[*] posted on 21-9-2018 at 08:31


There's this...
https://en.wikipedia.org/wiki/Ullmann_reaction
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Vanry
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[*] posted on 3-10-2018 at 07:12


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

I was tempted to give it a go, before reading that This reagent must be prepared and handled around -70°c ! :o 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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[*] posted on 3-10-2018 at 08:50


If you can get some dry ice, -70ºC is trivial with a dry ice/acetone bath.



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