Copper-Catalyzed Regioselective Nitration and Azidation of 1-Naphthylamine Derivatives via Remote C-H Activation

A simple and facile protocols for copper-catalyzed regionselective C4 nitration and azidation of 1-naphthylamines via remote C-H activation that use of pyridyl amide fragment as the removable directing group have been firstly developed. These reactions proceed under mild conditions without any additives, tolerate a wide variety of functional groups, and afford a wide range of products in good to excellent yields. Control experiments suggest that those C-H activation reactions are likely to proceed through a single-electron-transfer (SET) process.