Electrochemically Enabled, Nickel‐Catalyzed Amination

Chao Li, Yu Kawamata, Hugh Nakamura, Julien C. Vantourout, Zhiqing Liu, Qinglong Hou, Deng‐Hui Bao, Jeremy T. Starr, Jinshan Chen, Ming Yan,

Angewandte Chemie International Edition · 2017 · 308 citations · 66 references

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Concepts

Abstract

Along with amide bond formation, Suzuki cross-coupling, and reductive amination, the Buchwald-Hartwig-Ullmann-type amination of aryl halides stands as one of the most employed reactions in modern medicinal chemistry. The work herein demonstrates the potential of utilizing electrochemistry to provide a complementary avenue to access such critical bonds using an inexpensive nickel catalyst under mild reaction conditions. Of note is the scalability, functional-group tolerance, rapid rate, and the ability to employ a variety of aryl donors (Ar-Cl, Ar-Br, Ar-I, Ar-OTf), amine types (primary and secondary), and even alternative X-H donors (alcohols and amides).

References

66