DDQ-Catalyzed Direct C(sp 3 )–H Amination of Alkylheteroarenes: Synthesis of Biheteroarenes under Aerobic and Metal-Free Conditions

A strategy for oxidative Csp 3 –H/N–H cross-coupling is presented. This reaction successfully utilizes 2,3-dichloro-5,6-dicyano- p -benzoquinone (DDQ) and tert -butyl nitrite (TBN) as co-catalysts to construct the biomedical applicable biheteroarenes under aerobic conditions. Notably, this amination reaction is successful with a wide range of alkylheteroarenes and could be used as a functionalization tactic for pharmaceutical research and other areas. Furthermore, preliminary mechanistic studies indicate that the C–N bond formation proceeds through the nucleophilic attack of azole to the carbon cation.