$$\ce{RMgX + R'X' -> RR' + MgXX'}$$
Is this reaction possible?
I am not able find any reference to it in the books that I have. Anyone has a reference?
$\begingroup$
$\endgroup$
1
-
1$\begingroup$ Kindly go through this! Thanks chemistry.meta.stackexchange.com/q/86/106377 and this as well, chemistry.stackexchange.com/help/how-to-ask $\endgroup$– RishiJun 29, 2021 at 8:34
Add a comment
|
2 Answers
$\begingroup$
$\endgroup$
The reaction can also be done if catalyst is applied:
[...] we developed a unique cross-coupling reaction of alkyl halides with organomagnesium or organozinc reagents catalyzed by using a 1,3-butadiene as the additive. This reaction follows a new catalytic pathway: the Ni or Pd catalyst reacts first with R−MgX to form an anionic complex, which then reacts with alkyl halides. Bis-dienes were also effective additives for the Ni-catalyzed cross-coupling reaction of organozinc reagents with alkyl halides. This catalytic system tolerates a wide variety of functional groups, including nitriles, ketones, amides, and esters.
Source: Cross-Coupling Reaction of Alkyl Halides with Grignard Reagents Catalyzed by Ni, Pd, or Cu Complexes with π-Carbon Ligand(s), Jun Terao and Nobuaki Kambe Accounts of Chemical Research 2008 41 (11), 1545-1554 DOI: 10.1021/ar800138a
answered Jun 29, 2021 at 10:08
$\begingroup$
$\endgroup$
1
This reaction does not work for Grignards due to competing deprotonation and reduction reactions, however it is possible if you first modify the Grignard with copper to make the cuprate (Gilman reagent). There is a detailed explanation here
-
$\begingroup$ Extension: What are the pros and cons of using Gilman reagent over Grignard reagent to synthesize a hydrocarbon? $\endgroup$ Jun 29, 2021 at 10:20