Pentafluorocyclopropanation of (Hetero) arenes Using Sulfonium Salts: Applications in Late‐Stage Functionalization

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Abstract: The evaluation of the pentafluorocyclopropyl group as a chemotype in crop protection and medicinal chemistry has been hampered in the past by the lack of suitable methodologies that enable the practical incorporation of this moiety into advanced synthetic intermediates. Herein, we report the gram‐scale synthesis of an unprecedented sulfonium salt, 5‐(pentafluorocyclopropyl) dibenzothiophenium triflate, and its use as a versatile reagent for the photoinduced C−H pentafluorocyclopropylation of a broad series of non‐previously functionalized (hetero) arenes through a radical mediated mechanism. The scope and potential benefits of the protocol developed are further demonstrated by the late‐stage introduction of the pentafluorocyclopropyl unit into biologically relevant molecules and widely used pharmaceuticals.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Pentafluorocyclopropanation of (Hetero) arenes Using Sulfonium Salts: Applications in Late‐Stage Functionalization ; day:19 ; month:07 ; year:2023 ; extent:10
Angewandte Chemie / International edition. International edition ; (19.07.2023) (gesamt 10)

Creator: Feng, Zeyu
Riemann, Lucas
Guo, Zichen
Herrero, David
Simon, Martin
Golz, Christopher
Mata, Ricardo A.
Alcarazo, Manuel

DOI: 10.1002/anie.202306764

URN: urn:nbn:de:101:1-2023072015100072940590

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

Last update: 14.08.2025, 11:01 AM CEST

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Associated

Feng, Zeyu
Riemann, Lucas
Guo, Zichen
Herrero, David
Simon, Martin
Golz, Christopher
Mata, Ricardo A.
Alcarazo, Manuel

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