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Updated: Jan 16, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Visible-Light-Mediated Cascade Construction of Polysubstituted Naphthalene Scaffolds from 2-Methylbenzophenones and
Jian-Kang Sun1, Guang-Cai Ma1, Han Kai1
1Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing 210009, China.
Abstract:
We report a novel visible light-promoted cascade reaction for the efficient synthesis of substituted naphthalenes in good yields. Upon visible-light irradiation, 2-methylbenzophenones generate transient hydroxy-o-quinodimethanes, which act as nucleophiles to attack (trifluoromethyl)alkenes, forming key intermediates containing carbonyl and 1,1-difluoroalkene moieties. Subsequently, a visible light-driven intramolecular Paternò-Büchi reaction ([2 + 2] cycloaddition) occurs, followed by a retro-[2 + 2] process that yields substituted 1,2-dihydronaphthalenes with concomitant release of carbonyl fluoride. Finally, a dehydrogenative aromatization step affords the desired substituted naphthalenes.
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