Electrochemically Enabled, Nickel-Catalyzed Amination

Angew Chem Int Ed Engl. 2017 Oct 9;56(42):13088-13093. doi: 10.1002/anie.201707906. Epub 2017 Sep 14.

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).

Keywords: amination; arylation; cross-coupling; electrochemistry; nickel.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Amination
  • Amines / chemistry*
  • Benzyl Compounds / chemistry
  • Catalysis
  • Electrochemical Techniques
  • Electrodes
  • Nickel / chemistry*

Substances

  • Alcohols
  • Amines
  • Benzyl Compounds
  • Nickel
  • benzyl bromide