Electrochemically Enabled, Nickel‐Catalyzed Amination

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...

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Veröffentlicht in:Angewandte Chemie International Edition 2017-10, Vol.56 (42), p.13088-13093
Hauptverfasser: Li, Chao, Kawamata, Yu, Nakamura, Hugh, Vantourout, Julien C., Liu, Zhiqing, Hou, Qinglong, Bao, Denghui, Starr, Jeremy T., Chen, Jinshan, Yan, Ming, Baran, Phil S.
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Sprache:eng
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Zusammenfassung: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). Amination electrified: Arguably one of the most important types of bonds, the C−N bond, can now be forged under nickel‐catalysis with the aid of electrochemistry. Broad scope, scalability, sustainability, mildness, and rapid reacion rates are some highlights of this interesting new reaction. Tf=trifluoromethanesulfonyl.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201707906