4.8 Article

Nickel-Catalyzed Reductive and Borylative Cleavage of Aromatic Carbon-Nitrogen Bonds in N-Aryl Amides and Carbamates

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 15, Pages 5587-5590

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja501649a

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan
  2. Elements Strategy Initiative to Form Core Research Center from MEXT
  3. Grants-in-Aid for Scientific Research [23685021, 22105002] Funding Source: KAKEN

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The nickel-catalyzed reaction of N-aryl amides with hydroborane or diboron reagents resulted in the formation of the corresponding reduction or borylation products, respectively. Mechanistic studies revealed that these reactions proceeded via the activation of the C(aryl)-N bonds of simple, electronically neutral substrates and did not require the presence of an ortho directing group.

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