Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine

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Science Advances  09 Oct 2015:
Vol. 1, no. 9, e1500656
DOI: 10.1126/sciadv.1500656

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Copper-catalyzed aerobic oxidative C–H/N–H coupling between simple ketones and diamines was developed toward the synthesis of a variety of pyrazines. Various substituted ketones were compatible for this transformation. Preliminary mechanistic investigations indicated that radical species were involved. X-ray absorption fine structure experiments elucidated that the Cu(II) species 5 coordinated by two N atoms at a distance of 2.04 Å and two O atoms at a shorter distance of 1.98 Å was a reactive one for this aerobic oxidative coupling reaction. Density functional theory calculations suggested that the intramolecular coupling of cationic radicals was favorable in this transformation.

  • Copper-Catalyzed
  • Aerobic Oxidative Coupling
  • C-N Bond Formation
  • EPR
  • XAFS
  • DFT Calculations

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