Truesdell BL,
Hamby TB,
Sevov CS.
* The Ohio State University, Columbus, USA
General C(sp
2)–C(sp
3) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts.
J. Am. Chem. Soc. 2020;
142: 5884-5893
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.
