Abstract
AbstractIn Ullmann‐type C−N coupling reactions, the involvement of CuIII species has been proposed many times on the basis of the oxidative addition–reductive elimination (OA‐RE) path for these reactions, but actual species could not be traced in experimental studies. In the C−N coupling reactions, carbonate and phosphate were considered widely as bases. In the present study, Cu‐mediated C−N coupling reactions of aryl halides and NuNH (amide and imide) were investigated extensively, and we provide direct spectroscopic evidence of actual CuIII species. For the first time, we reveal that carbonate and phosphate ions act as bidentate ligands as well as a base in the catalytic cycle, and thus the actual intermediate species is a carbonate‐ or phosphate‐ligated, distorted octahedral CuIII complex. Our experimental and computational studies have strengthened the hypothesis that these reactions follow an OA‐RE path.
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