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Synfacts 2020; 16(10): 1173
DOI: 10.1055/s-0040-1706433
Metals in Synthesis

Palladium-Catalyzed Cross-Couplings of Alkyllithiums with Aryl Chlorides

Contributor(s):
Paul Knochel
,
Alexander Kremsmair
Scherpf T, Steinert H, Großjohann A, Dilchert K, Tappen J, Rodstein I, Gessner VH. * Ruhr-Universität Bochum, Germany
Efficient Pd-Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents.

Angew. Chem. Int. Ed. 2020;
DOI: 10.1002/anie.202008866
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Key words

palladium catalysis - organolithium - cross-coupling - ylides

Significance

Gessner and co-workers report the palladium-catalyzed cross-coupling of aryl chlorides with alkyllithium reagents under mild conditions in good to excellent yields. Furthermore, gram-scale reactions were performed, demonstrating the scalability of this protocol.


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Comment

The authors performed extensive screening and discovered a suitable catalyst based on ylide-substituted phosphines which gave good selectivities combined with high yields, preventing several undesired side-reactions such as homo­coupling, isomerization or protodehalogenation. In addition, the catalyst proved to be successful for Kumada type cross-couplings.


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Publication History

Article published online:
17 September 2020

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