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Updated: Sep 13, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Tunable Formal Photocycloaddition of 1-Naphthol Derivatives
Qinqin Wu1, Shuo Yang2, Minyan Wang2
1Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, China.
Abstract:
Although three different modes of photocycloaddition between arenes and alkenes are well-known, the control of reaction selectivity remains a long-standing challenge. In this study, we present the first tunable photocycloaddition of 1-naphthol derivatives under visible light irradiation, affording ortho, meta, and para cycloadducts, respectively. The success of the reaction hinges on a rational design of naphthalene substrates and the judicious selection of solvents and sensitizer. The reaction mechanism is further elucidated through a combination of control experiments and density functional theory (DFT) calculations.
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