4.8 Article

Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes

Journal

CHEMICAL SCIENCE
Volume 10, Issue 27, Pages 6666-6671

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc02035g

Keywords

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Funding

  1. JSPS KAKENHI [15H03811]
  2. MEXT, Japan [18H04259]
  3. Toray Science Foundation
  4. Hoansha Foundation
  5. Program for Leading Graduate Schools: Interactive Materials Science Cadet Program
  6. Grants-in-Aid for Scientific Research [15H03811, 18H04259] Funding Source: KAKEN

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Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes is developed. This method can be used to produce a variety of N-aryl heteroarenes, including pyrroles, indoles, carbazoles and phenoxazines, using benzoic acid derivatives as arylating reagents. Arylnickelamide intermediates that are relevant to the catalytic reaction were characterized by X-ray crystallography. When N-acylated benzimidazoles are used as substrates, decarbonylation accompanied 1,2-migration to form 2-arylated benzimidazoles.

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