Iron(iii)-catalyzed chelation assisted remote C-H bond oxygenation of 8-amidoquinolines

Org Biomol Chem. 2017 Nov 7;15(43):9200-9208. doi: 10.1039/c7ob02159c.

Abstract

Iron catalyzed site selective and chelation assisted C-H functionalization in 8-amidoquinolines is achieved. The remote C5-benzoxylation with benzoyl peroxide produced a variety of potentially bioactive 8-arylcarboxamido-5-benzoyloxy quinoline derivatives. The efficiency of the reaction reflects from the wide substrate scope with electronic differentiation on carboxamide and acyl peroxide in addition to tolerance of halo-substitutions on either of the aryls. The reaction is additive, silver free and proceeds without the exclusion of air or moisture.