RSS-Feed abonnieren
DOI: 10.1055/s-0029-1216682
Nickel-Catalyzed Coupling of Alkyl Halides and Alkyl Grignard Reagents
Rezensent(en):Paul Knochel, Andrei GavryushinEcole Polytechnique Fédérale de Lausanne, Switzerland
Nickel-Catalyzed Cross-Coupling of Non-Activated and Functionalized Alkyl Halides with Alkyl Grignard Reagents
Angew. Chem. Int. Ed. 2009, 48: 2937-2940
Publikationsverlauf
Publikationsdatum:
25. Mai 2009 (online)
Key words
alkyl halides - cross-coupling - Grignard reagents - nickel complexes
![](https://www.thieme-connect.de/media/synfacts/200906/p046_s1.gif)
Significance
Grignard reagents are desirable nucleophiles in coupling
reactions, since they are inexpensive and easy to prepare. The use
of a
pincer nickel complex (1)
enables their highly efficient sp³-sp³ cross-coupling
with alkyl bromides and iodides. The reaction proceeds at low temperatures,
so that even highly reactive functionalities like ketones are tolerated.
Comment
Alkyl bromides and alkyl iodides react at similar rates, while
alkyl chlorides are inert. Interestingly, aryl bromides do not participate
in the coupling under these conditions. N,N-Dimethylacetamide (its mixture
with THF) is the solvent of choice, NMP and other solvents give
lower yields. Nickel(IV)-bis(alkyl) intermediates are tentative
intermediates
in this reaction.
![](https://www.thieme-connect.de/media/synfacts/200906/p046_s1.gif)