Selective and Sequential Aryne Generations to Build Multisubstituted Naphthalenes

Keywords

naphthalenes - selective aryne generation - polyaromatic hydrocarbons

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.

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.