Affiliation:
1. Institut für Organische und Biomolekulare Chemie Georg-August-Universität Göttingen Tammannstr 2 37077 Göttingen Germany
2. Institut für Physikalische Chemie Georg-August-Universität Göttingen Tammannstr 6 37077 Göttingen Germany
Abstract
AbstractThe 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.
Funder
H2020 European Research Council
Deutsche Forschungsgemeinschaft
Subject
General Chemistry,Catalysis
Cited by
1 articles.
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