Making the SF5 Group More Accessible: A Gas‐Reagent‐Free Approach to Aryl Tetrafluoro‐λ6‐sulfanyl Chlorides

Group therapy: Employing easy‐to‐handle trichloroisocyanuric acid, potassium fluoride, and catalytic amounts of acid allows simple, mild and direct access to aryl‐SF₄Cl intermediates that have either not been or cannot be prepared using other methods. The approach also provides access to aryl‐SF₃ and aryl‐SeF₃ compounds, which extend the applications of this chemistry beyond arene SF₅‐functionalization.

Abstract

Modern pentafluorosulfanyl (SF₅) chemistry has an Achilles heel: synthetic accessibility. Herein, we present the first approach to aryl‐SF₄Cl compounds (key intermediates in state‐of‐the‐art aryl‐SF₅ synthesis) that overcomes the reliance on hazardous fluorinating reagents and/or gas reagents (e.g. Cl₂) by employing easy‐to‐handle trichloroisocyanuric acid, potassium fluoride, and catalytic amounts of acid. These simple, mild conditions allow direct access to aryl‐SF₄Cl intermediates that either have not been or cannot be demonstrated using previous methods. Furthermore, the same approach provides access to aryl‐SF₃ and aryl‐SeF₃ compounds, which extend the applications of this chemistry beyond arene SF₅‐functionalization, and demonstrate its ability to address a more general oxidative fluorination problem.

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