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1.10 The Pentafluorosulfanyl Group (SF5)
Book
Editor: Paquin, J.-F.
Title: Modern Strategies in Organofluorine Chemistry 1
Online ISBN: 9783132458253; Book DOI: 10.1055/b000000921
1st edition © 2024. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
The pentafluorosulfanyl group imparts exceptional thermal, chemical, and metabolic stability to organic scaffolds. Despite being first described seven decades ago, it remains an under-utilized motif in organofluorine chemistry, primarily due to a lack of efficient synthetic routes that proceed under mild reaction conditions. Nonetheless, the renewed interest in pentafluorosulfanyl scaffolds over the last decade has enabled the preparation of important pentafluorosulfanyl building blocks. Herein, the major synthetic strategies for the preparation of pentafluoro-λ6-sulfanyl-containing compounds are reviewed, including the synthesis of (pentafluorosulfanyl)arenes via oxidative halogenation and the direct pentafluorosulfanylation of aliphatic cores, achieved mainly using pentafluorosulfanyl chloride as a reagent.
Key words
pentafluorosulfanyl compounds - fluorine - fluorination - sulfur - oxidative fluorination - chlorine - chlorotetrafluorosulfanyl compounds - arenes - aliphatic compounds - unsaturated compounds- 1 Weinhold F, Landis CR. Valency and Bonding: A Natural Bond Orbital Donor–Acceptor Perspective. Cambridge University Press; Cambridge 2005
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