# Solvent-Controlled Regiodivergent Friedel–Crafts Reactions of 1‑Naphthol with In Situ Generated Aza‑o‑Quinone Methides

## TL;DR

This study shows how changing the solvent can control where a chemical reaction occurs on a molecule, enabling the production of different triarylmethane compounds.

## Contribution

A solvent-controlled regiodivergent Friedel–Crafts reaction of 1-naphthol with aza-o-quinone methides is introduced.

## Key findings

- Ortho-selective reactions occur in toluene, while para-selective reactions occur in acetonitrile.
- A range of functionalized triarylmethanes were synthesized using this method.
- Theoretical studies provided insights into the site-selective reaction mechanism.

## Abstract

In this study, we reported a solvent-controlled site-selectivity
switchable Friedel–Crafts reaction of 1-naphthols with in situ
generated aza-o-quinone methides. The ortho-selective Friedel–Crafts reaction was achieved in toluene,
while the para-selective Friedel–Crafts reaction
was accomplished in acetonitrile. With this protocol, a range of functionalized
triarylmethanes were prepared. Moreover, theoretical mechanistic investigations
provided insights into the site-selective reaction pathway.