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

## TL;DR

This paper explores how certain benzene compounds react with aryl diazonium salts to form new azo products under mild conditions.

## Contribution

The study reveals new mechanistic insights and identifies novel reaction intermediates in azo-coupling reactions.

## Key findings

- Novel azo-coupling products were formed in high yields under mild conditions.
- 1H-NMR monitoring revealed the relative reactivity of the reagents and new intermediates.
- The electrophilic aromatic substitution mechanism was studied in detail.

## Abstract

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.