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Electrochemically Enabled, Nickel-Catalyzed Amination.

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).

SUBMITTER: Li C

PROVIDER: S-EPMC5792186 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Electrochemically Enabled, Nickel-Catalyzed Amination.

Li Chao C Kawamata Yu Y Nakamura Hugh H Vantourout Julien C JC Liu Zhiqing Z Hou Qinglong Q Bao Denghui D Starr Jeremy T JT Chen Jinshan J Yan Ming M Baran Phil S PS

Angewandte Chemie (International ed. in English) 20170914 42

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 a ...[more]

PMID: 28834098

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