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

Brägger, Yannick

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

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

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Item Permalink: https://hdl.handle.net/21.11116/0000-000D-BFAD-A Version Permalink: https://hdl.handle.net/21.11116/0000-0010-DA91-4

Genre: Thesis

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Creators:
Brägger, Yannick¹, Author

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1Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, DE, ou_2040309

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Abstract: 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.

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Language(s): eng - English

Dates: Accepted: 2021-02-27Date issued: 2021-02-27

Publication Status: Issued

Pages: 101

Publishing info: Zürich : Eidgenössische Technische Hochschule Zürich

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Degree: Master

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