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Synfacts 2020; 16(06): 0661
DOI: 10.1055/s-0040-1706971
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Cross-Electrophile Coupling using Electrochemistry

Contributor(s):
Paul Knochel
,
Ferdinand H. Lutter
Truesdell BL, Hamby TB, Sevov CS. * The Ohio State University, Columbus, USA
General C(sp2)–C(sp3) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts.

J. Am. Chem. Soc. 2020;
142: 5884-5893
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Further Information

Publication History

Publication Date:
15 May 2020 (online)

 
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Key words

electrochemistry - nickel catalysis - cross-electrophile coupling

Significance

The authors describe a general nickel-catalyzed cross-electrophile coupling of functionalized alkenyl, aryl, and heteroaryl halides with various primary and secondary bromides using electrochemistry. The alkylated products were obtained in high yields.


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Comment

Key for high coupling yields was the use of the electron shuttle reagent Ni(η3-L)2, which efficiently prevents over-reduction and thus decomposition of the unsaturated halides. Significantly, this enables an easy scale up by performing the reaction at high currents on a 75 mmol scale.


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