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

摘要

Sulfur(VI) fluoride exchange (SuFEx) is a new family of click chemistry based transformations that enable the synthesis of covalently linked modules via S-VI hubs. Here we report thionyl tetrafluoride (SOF4) as the first multidimensional SuFEx connector. SOF4 sits between the commercially mass-produced gases SF6 and SO2F2, 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.