Aryl diazonium salts and benzene derivatives bearing two electron-donor substituents: chemical and mechanistic behaviours

The reaction between benzene derivatives 1-4 and p-substituted benzenediazonium tetrafluoroborates 5a-c provided novel azo-coupling products in high yields under mild conditions. The monitoring of the reaction progress using 1H-NMR provided mechanistic information on both the relative reactivity of the reagents and the possibility to detect novel reaction intermediates. Study of the electrophilic aromatic substitution reaction between benzenediazonium salts and neutral carbon nucleophiles.