Research ArticleORGANIC CHEMISTRY

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

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

You are currently viewing the abstract.

View Full Text

Abstract

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.

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

This is an open-access article distributed under the terms of the Creative Commons Attribution-NonCommercial license, which permits use, distribution, and reproduction in any medium, so long as the resultant use is not for commercial advantage and provided the original work is properly cited.

View Full Text

More Like This