Synthesis of Nitrobenzenes from Pyridines.

A pyridine to benzene skeletal-editing system for nitrobenzene synthesis is described. 4-Substituted pyridines undergo one-pot transformation with nitromethane using nonafluorobutanesulfonic anhydride (Nf2O) as activating group, whereas 3-substituted pyridines were transformed using a trifluoromethane sulfonic anhydride (Tf2O) Zincke imine approach. The transformation installs the versatile nitro group meta to traditional ortho/para-directing substituents, complementing classic electrophilic aromatic substitution patterns of reactivity.