Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF₄ Hub

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Abstract

Sulfur(VI) fluoride exchange (SuFEx) is a new family of click chemistry based transformations that enable the synthesis of covalently linked modules via SVI hubs. Here we report thionyl tetrafluoride (SOF₄ ) as the first multidimensional SuFEx connector. SOF₄ sits between the commercially mass-produced gases SF₆ and SO₂ F₂ , and like them, is readily synthesized on scale. Under SuFEx catalysis conditions, SOF₄ reliably seeks out primary amino groups [R-NH₂ ] and becomes permanently anchored via a tetrahedral iminosulfur(VI) link: R-N=(O=)S(F)₂ . The pendant, prochiral difluoride groups R-N=(O=)SF₂ , in turn, offer two further SuFExable handles, which can be sequentially exchanged to create 3-dimensional covalent departure vectors from the tetrahedral sulfur(VI) hub.

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