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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.


 

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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