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Hypervalent Sulfur Derivatives as Sulfenylating Reagents: Visible-Light-Mediated Direct Thiolation of Activated C(sp2)-H Bonds with Dihalosulfuranes.
Kuznetsova, Elizaveta A; Rysaeva, Regina R; Smolobochkin, Andrey V; Gazizov, Almir S; Gerasimova, Tatyana P; Gerasimova, Daria P; Lodochnikova, Olga A; Morozov, Vladimir I; Vatsadze, Sergey Z; Burilov, Alexander R; Pudovik, Michail A.
Afiliación
  • Kuznetsova EA; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Street 8, Kazan 420088, Russian Federation.
  • Rysaeva RR; Kazan National Research Technological University, Karla Marksa Street 68, Kazan 420015, Russian Federation.
  • Smolobochkin AV; Organic Chemistry Department, Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya 18, Kazan 420008, Russian Federation.
  • Gazizov AS; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Street 8, Kazan 420088, Russian Federation.
  • Gerasimova TP; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Street 8, Kazan 420088, Russian Federation.
  • Gerasimova DP; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Street 8, Kazan 420088, Russian Federation.
  • Lodochnikova OA; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Street 8, Kazan 420088, Russian Federation.
  • Morozov VI; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Street 8, Kazan 420088, Russian Federation.
  • Vatsadze SZ; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Street 8, Kazan 420088, Russian Federation.
  • Burilov AR; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russian Federation.
  • Pudovik MA; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Street 8, Kazan 420088, Russian Federation.
Org Lett ; 26(20): 4323-4328, 2024 May 24.
Article en En | MEDLINE | ID: mdl-38723192
ABSTRACT
In contrast to hypervalent iodine compounds, the chemistry of their sulfur analogues has been considerably less explored. Herein, we report the direct C-H bond thiolation of electron-rich heterocycles, arenes, and 1,3-dicarbonyls by dichlorosulfuranes under mild conditions. Mechanistic studies and density functional theory calculations suggest the radical chain mechanism of the disclosed transformation. The key to success is attributed to a strikingly low S-Cl bond dissociation energy, which enables the generation of radical species upon exposure to daylight.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article Pais de publicación: Estados Unidos