Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF4Hub.
Sulfur(VI) fluoride exchange (SuFEx) is a new family of click chemistry based transformations that enable the synthesis of covalently linked modules via SVIhubs. Here we report thionyl tetrafluoride (SOF4) as the first multidimensional SuFEx connector. SOF4sits between the commercially mass-produced gases SF6and SO2F2, and like them, is readily synthesized on scale. Under SuFEx catalysis conditions, SOF4reliably 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.
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Suhua
S
Li
Department of Chemical Physiology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Peng
P
Wu
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.|School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK.
John E
JE
Moses
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
K Barry
KB
Sharpless
D057930:Click Chemistry; D005459:Fluorides / Q000737:chemistry*; D015394:Molecular Structure; D013455:Sulfur / Q000737:chemistry*
D013455:Sulfur; D005459:Fluorides
SuFEx reaction; amines; click chemistry; phenols; thionyl tetrafluoride