Ex situ Generation of Thiazyl Trifluoride (NSF3) as a Gaseous SuFEx Hub** |
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| Authors: | Bing-Yu Li Kexin Su Prof Dr Luc Van Meervelt Prof Dr Steven H L Verhelst Dr Ermal Ismalaj Prof Dr Wim M De Borggraeve Dr Joachim Demaerel |
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| Institution: | 1. Sustainable Chemistry for Metals and Molecules (SCM2), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Box 2404, 3001 Leuven, Belgium;2. Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, PO Box 2404, 3001 Leuven (Heverlee), Belgium;3. Laboratory of Chemical Biology, Department of Cellular and Molecular Medicine, KU Leuven, O&N I bis, Herestraat 49, box 901, 3000 Leuven, Belgium |
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| Abstract: | Sulfur(VI)-fluoride exchange (SuFEx) chemistry, an all-encompassing term for substitution events that replace fluoride at an electrophilic sulfur(VI), enables the rapid and flexible assembly of linkages around a SVI core. Although a myriad of nucleophiles and applications works very well with the SuFEx concept, the electrophile design has remained largely SO2-based. Here, we introduce S≡N-based fluorosulfur(VI) reagents to the realm of SuFEx chemistry. Thiazyl trifluoride (NSF3) gas is shown to serve as an excellent parent compound and SuFEx hub to efficiently synthesize mono- and disubstituted fluorothiazynes in an ex situ generation workflow. Gaseous NSF3 was evolved from commercial reagents in a nearly quantitative fashion at ambient conditions. Moreover, the mono-substituted thiazynes could be extended further as SuFEx handles and be engaged in the synthesis of unsymmetrically disubstituted thiazynes. These results provide valuable insights into the versatility of these understudied sulfur functionalities paving the way for future applications. |
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| Keywords: | Click Chemistry Sufex Chemistry Synthetic Methods Thiazyl Trifluoride Thiazyne |
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