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Synfacts 2015; 11(8): 0853
DOI: 10.1055/s-0034-1381127
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ligand-Free Copper-Catalyzed Negishi Cross-Coupling

Contributor(s):
Paul Knochel
,
Diana Haas
Thapa S, Kafle A, Gurung SK, Montoya A, Riedel P, Giri R * The University of New Mexico, Albuquerque, USA
Ligand-Free Copper-Catalyzed Negishi Coupling of Alkyl-, Aryl-, and Alkynylzinc Reagents with Heteroaryl Iodides.

Angew. Chem. Int. Ed. 2015;
54: 8236-8240
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Publication History

Publication Date:
20 July 2015 (online)

 
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Key words

Negishi cross-coupling - copper - heteroaryls

Significance

A ligand-free, copper-catalyzed Negishi cross-coupling of various zinc reagents with heteroaryl iodides affording the desired coupling products in very high yields is reported. The reaction proceeds within three hours at room ­temperature for alkylzinc reagents; however, higher temperatures are required for coupling with aryl- and alkynylzinc reagents.


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Comment

Interestingly, no β-hydride elimination or rearrangement was observed for the coupling with primary, secondary, or tertiary alkylzinc reagents. Moreover, a variety of functional groups are tolerated in this protocol.


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