A Flash Conversion to Aromatic Azo Compounds Expedited by Hydrazine–Trifluoroacetate Hydrogen Bonding

Aromatic
azo compounds are very useful
chemicals, but
rapid and
safe synthetic methods for preparing these compounds are underexplored.
An extremely fast reaction was developed to prepare aromatic azo compounds
from commercially available quinones and aryl hydrazinium chloride
salts. The reactions could be completed within 2 min, in the presence
of sodium trifluoroacetate under ambient conditions. A hydrazine–trifluoroacetate
hydrogen bonding complex likely inhibited byproducts and greatly accelerated
the reaction. The overall procedure is extremely simple and does not
require sophisticated synthetic organic equipment and techniques.