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DOI: 10.1055/a-2557-9611
Selective and Sequential Aryne Generations to Build Multisubstituted Naphthalenes
Synthesis of Multisubstituted Naphthalenes through Consecutive Aryne Reactions.
Bull. Chem. Soc. Jpn. 2025;
98: uoaf001
DOI: 10.1093/bulcsj/uoaf001

Significance
This study presents a method for synthesizing multisubstituted naphthalenes through consecutive aryne reactions, addressing the challenge of regioselectivity in aromatic functionalization. By leveraging naphthodiyne intermediates and selective reagent-controlled activation of silyl and iodo groups, the authors achieve precise transformations, expanding the synthetic toolkit for polycyclic aromatic hydrocarbons. The approach offers a modular and efficient strategy for constructing diverse naphthalene derivatives, which hold significant potential in pharmaceuticals, materials science, and chemical biology.
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Comment
The study effectively leverages aryne chemistry for constructing complex naphthalene
core compounds. Based on their previous research, the authors combined their knowledge
on selective aryne activation and applied it to a new core. They use an organometallic
activator (Grignard) to generate the aryne at the o-iodoaryl triflates, and cesium fluoride to activate the o-silylaryl triflate moiety. While the starting material preparation requires several
steps, the aryne functionalization reactions run smoothly with good yield and moderate
regioselectivity.
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Publication History
Article published online:
22 April 2025
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