Cu(OAc)2-Promoted Ortho C(sp2)-H Amidation of 8-Aminoquinoline Benzamide with Acyl Azide: Selective Formation of Aroyl or Acetyl Amide Based on Catalyst Loading.

An efficient method for the C(sp2) amidation of 8-aminoquinoline benzamide by acyl azide in the presence of copper acetate has been achieved via C-H activation. Interestingly, the loading of copper acetate has a strong influence on the outcome of the reaction. The use of 1 equiv of copper acetate produces the corresponding aroyl amide, whereas the use of 2 equiv led to acetyl amide. A series of substituted benzoyl and acetyl amides has been obtained.