- Metal-Free Visible-Light-Mediated Aromatization of 1,2–Dihydronaphthalenes
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A series of polyaromatic naphthalenes have been synthesized through the dehydrogenation of the corresponding 1,2-dihydroarylnaphthalenes by using 9-mesityl-10-methylacridinium perchlorate as a photocatalyst and diphenyliodonium triflate as an external oxidant under visible light irradiation. The reaction proceeds smoothly under metal-free conditions and tolerates some functionalities. Interestingly, the reaction is also amenable to the aromatization of tetrahydronaphthalenes and fair conversions were obtained. Preliminary mechanistic investigations have been conducted and a reasonable mechanism is proposed.
- Rammal, Fatima,Gaumont, Annie-Claude,Lakhdar, Sami
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supporting information
p. 1482 - 1485
(2019/12/12)
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- Calcium-catalyzed carboarylation of alkynes
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The first transition-metal-free carboarylation of alkynes with commercial and readily available alcohols as alkylating agents was realized in the presence of an environmentally benign calcium catalyst. Thereby, a novel protocol for the one-step synthesis of highly congested, all-carbon tetrasubstituted alkenes, as incorporated in potentially bioactive, complex dihydronaphthalene, chromene and dihydroquinoline structures, is provided. The reaction features an unprecedented, particularly wide substrate scope, good functional-group tolerance and simple experimental operation under mild reaction conditions. Finally free: The first transition-metal-free one-step synthesis of highly congested, all-carbon tetrasubstituted olefins has been realized by a calcium-catalyzed carboarylation reaction. Internal alkynes react with alcohols as alkylating reagent under mild reaction conditions, which provides access to a variety of useful structural scaffolds via highly reactive trisubstituted vinyl cations.
- Fu, Liang,Niggemann, Meike
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supporting information
p. 6367 - 6370
(2015/04/22)
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- Copper-catalyzed carboarylation of alkynes via vinyl cations
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Copper-catalyzed arylation of electron rich alkynes reveals stabilized trisubstituted vinyl cation equivalents that react with pendant arene nucleophiles to form all carbon tetrasubstituted alkenes. The new process streamlines the synthesis of important medicinally relevant molecules.
- Walkinshaw, Andrew J.,Xu, Wenshu,Suero, Marcos G.,Gaunt, Matthew J.
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supporting information
p. 12532 - 12535
(2013/09/23)
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