Electrophilic Vinylation of Thiols under Mild and Transition Metal‐Free Conditions

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Abstract: The iodine (III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E‐alkenyl sulfides with complete chemo‐ and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal‐free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl‐substituted core.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Electrophilic Vinylation of Thiols under Mild and Transition Metal‐Free Conditions ; volume:132 ; number:36 ; year:2020 ; pages:15642-15646 ; extent:5
Angewandte Chemie ; 132, Heft 36 (2020), 15642-15646 (gesamt 5)

Creator: Castoldi, Laura
Di Tommaso, Ester Maria
Reitti, Marcus
Gräfen, Barbara
Olofsson, Berit

DOI: 10.1002/ange.202002936

URN: urn:nbn:de:101:1-2022052911412466508155

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 05.01.2025, 2:29 PM CET

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Associated

Castoldi, Laura
Di Tommaso, Ester Maria
Reitti, Marcus
Gräfen, Barbara
Olofsson, Berit

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