4.8 Article

Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 22, Pages 9872-9878

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b13117

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Funding

  1. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  2. NSF of China [21821002, 21772222, 91956112]
  3. SAMP
  4. TCSM of Shanghai [17JC1401200, 18JC1415600, 19YF1458500]

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A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.

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