Pentafluorocyclopropanation of (Hetero)arenes Using Sulfonium Salts: Applications in Late‐Stage Functionalization
2023 | journal article. A publication with affiliation to the University of Göttingen.
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Pentafluorocyclopropanation of (Hetero)arenes Using Sulfonium Salts: Applications in Late‐Stage Functionalization
Feng, Z.; Riemann, L.; Guo, Z.; Herrero, D.; Simon, M.; Golz, C. & Mata, R. A. et al. (2023)
Angewandte Chemie International Edition, 62(35) art. e202306764. DOI: https://doi.org/10.1002/anie.202306764
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Details
- Authors
- Feng, Zeyu; Riemann, Lucas; Guo, Zichen; Herrero, David; Simon, Martin; Golz, Christopher; Mata, Ricardo A.; Alcarazo, Manuel
- Abstract
- 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.
- Issue Date
- 2023
- Journal
- Angewandte Chemie International Edition
- ISSN
- 1433-7851
- eISSN
- 1521-3773
- Language
- English
- Sponsor
- H2020 European Research Council https://doi.org/10.13039/100010663
Deutsche Forschungsgemeinschaft https://doi.org/10.13039/501100001659