Oxidation Potential Tunable Organic Molecules and Their Catalytic Application to Aerobic Dehydrogenation of Tetrahydroquinolines.

In this work, oxidation potential tunable organic molecules, alkyl 2-phenyl hydrazocarboxylates, were disclosed. The exquisite tuning of their oxidation potentials facilitated a catalytic dehydrogenation of 1,2,3,4-tetrahydroquinolines in the presence of Mn(Pc) and O2.

Cu-Catalyzed Aerobic Oxidation of Di-tert-butyl Hydrazodicarboxylate to Di-tert-butyl Azodicarboxylate and Its Application on Dehydrogenation of 1,2,3,4-Tetrahydroquinolines under Mild Conditions.

A new class of co-catalytic system was developed with homogeneous CuI and di-tert-butyl azodicarboxylate for aerobic dehydrogenation of 1,2,3,4-tetrahydroquinolines under mild conditions. The developed co-catalytic system is consisting of di-tert-butyl azodicarboxylate-mediated dehydrogenation of 1,2,3,4-tetrahydroquinoline and aerobic oxidative regeneration of di-tert-butyl azodicarboxylate from di-tert-butyl hydrazodicarboxylate using molecular oxygen as a terminal oxidant. A variety of quinolines were efficiently synthesized by the developed Cu and di-tert-butyl azodicarboxylate co-catalytic system.