Solvent-Controlled Regiodivergent Friedel–Crafts Reactions of 1‑Naphthol with In Situ Generated Aza‑o‑Quinone Methides
Si-Kai Liu, Salha Alotaibi, Jen-Yu Kuan, Theo P. Gonçalves, Kuo-Wei Huang, Jeng-Liang Han
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.
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.
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Taxonomy
TopicsSynthesis of Indole Derivatives · Axial and Atropisomeric Chirality Synthesis · Chemical Reaction Mechanisms