4.8 Article

Photocatalytic C-H Amination of Aromatics Overcoming Redox Potential Limitations

Journal

ORGANIC LETTERS
Volume 22, Issue 7, Pages 2822-2827

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00822

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Funding

  1. MEXT
  2. JSPS KAKENHI [JP19K15570]
  3. Tobe Maki Foundation
  4. Tokyo Ohka Foundation for The Promotion of Science and Technology
  5. Fukuoka Naohiko Foundation

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We report the photocatalytic C-H amination of aromatics overcoming redox potential limitations. Radical cations of aromatic compounds are generated photocatalytically using Ru(phen)(3)(PF6)(2), which has a reduction potential at a high oxidation state (E-red(Ru-III/Ru-II) = +1.37 V vs SCE) lower than the oxidation potentials of aromatic substrates (E-ox = +1.65 to +2.27 V vs SCE). The radical cations are trapped with pyridine to give N-arylpyridinium ions, which were converted to aromatic amines.

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