Transition‐Metal‐Free Difunctionalization of Sulfur Nucleophiles **
Abstract: Efficient protocols for accessing iodo‐substituted diaryl and aryl (vinyl) sulfides have been developed using iodonium salts as reactive electrophilic arylation and vinylation reagents. The reactions take place under transition‐metal‐free conditions, employing odorless and convenient sulfur reagents. A wide variety of functional groups are tolerated in the S‐diarylation, enabling the regioselective late‐stage application of several heterocycles and drug molecules under mild reaction conditions. A novel S‐difunctionalization pathway was discovered using vinyliodonium salts, which proceeds under additive‐free reaction conditions and grants excellent stereoselectivity in the synthesis of aryl (vinyl) sulfides. A one‐pot strategy combining transition‐metal‐free diarylation and subsequent reduction provided facile access to electron‐rich thioanilines and a direct synthesis of a potential drug candidate derivative. The retained iodo group allows a wide array of further synthetic transformations. Mechanistic insights were elucidated by isolating the key intermediate, and the relevant energy profile was substantiated by DFT calculations.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Transition‐Metal‐Free Difunctionalization of Sulfur Nucleophiles ** ; day:13 ; month:01 ; year:2023 ; extent:9
Angewandte Chemie / International edition. International edition ; (13.01.2023) (gesamt 9)
- Urheber
- DOI
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10.1002/anie.202216296
- URN
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urn:nbn:de:101:1-2023011414122274414191
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:38 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Mondal, Shobhan
- Di Tommaso, Ester Maria
- Olofsson, Berit
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