Synfacts 2019; 15(01): 0049
DOI: 10.1055/s-0037-1611417
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

The First Csp2–Csp2 Cross-Coupling Using Organozinc Reagents

Contributor(s):
Paul Knochel
,
Ferdinand H. Lutter
Further Information

Publication History

Publication Date:
14 December 2018 (online)

 

Significance

In 1977, Negishi and co-workers described the first transition-metal-catalyzed cross-coupling using aryl- and benzylzinc reagents with substituted aryl halides. Two catalytic systems using either nickel or palladium salts in combination with PPh3 were developed leading to the coupling products in high yields.


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Comment

In comparison to the corresponding magnesium-based organometallics, the use of organozinc species enables the coupling of aryl halides bearing sensitive functional moieties, such as ester, nitrile, or even nitro groups. Due to the low toxicity of organozinc reagents, and the mild conditions required for the cross-coupling, their application in academic and industrial research remains a growing field.


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Review

D. Haas, J. M. Hammann, R. Greiner, P. Knochel ACS Catal. 2016, 6, 1540–1552.


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