Visible Light Photoredox Catalysis Enables Radical-Polar Crossover for Modular 
Carbofunctionalization of Alkyl Thianthrenium Salts

Brägger, Yannick

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Visible Light Photoredox Catalysis Enables Radical-Polar Crossover for Modular Carbofunctionalization of Alkyl Thianthrenium Salts

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Brägger, Yannick
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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引用

Brägger, Y. (2021). Visible Light Photoredox Catalysis Enables Radical-Polar Crossover for Modular Carbofunctionalization of Alkyl Thianthrenium Salts. Master Thesis, Eidgenössische Technische Hochschule Zürich, Zürich.

引用: https://hdl.handle.net/21.11116/0000-000D-BFAD-A

要旨

A photoredox-catalyzed Giese Reaction was developed for the hydroalkylation of vinyl thianthrenium salts. The mechanism of this transformation follows a RPC pathway and is catalyzed by a mesity-lacridnium photocatalyst. Multiple linear alkyl thianthrenium salts were obtained in good to excellent yields, demonstrating for the first time that radical addition to alkenyl sulfonium salts is possible. We could also show that substituted alkenyl thianthrenium salts also engage in the desired reactivity, albeit with the downside of catalyst decomposition. Lastly, we showed that alkyl thianthrenium salts are excellent electrophiles for nucleophilic substitution, with multiple examples furnishing excellent yields. We also showed that S-ylides of alkyl thianthrenium salts are stable species that can engage in the same reactivity as other S-ylides.