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While sulfonamides, sulfones, and sulfates dominate existing drug scaffolds, more complex, multidirectional sulfur(VI) cores remain underexplored. Here, we show a viable route from amino difluorothiazynes to aminosulfurdiimidoyl fluorides (ASDFs), via sequential alkylation and imination. Leveraging the ambiphilic character of fluorothiazynes\u2014acting as both N\u2010nucleophile and S\u2010electrophile\u2014we generate thiazynium intermediates that, upon trapping with primary amides, afford ASDFs in good yields. Additionally, the potential of ASDFs as SuFEx electrophiles is demonstrated by reaction with various nucleophiles. Notably, a sulfurdiimidamide derivative was generated, which is likely the first unsymmetrically substituted tetraimidosulfur species. This work expands the toolkit of azasulfur(VI) fluorides, introducing the first general route to ASDFs as stable, functionally diverse platforms for further chemical diversification.<\/jats:p>","DOI":"10.1002\/anie.202523033","type":"journal-article","created":{"date-parts":[[2025,12,13]],"date-time":"2025-12-13T02:59:36Z","timestamp":1765594776000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Fluorothiazynes as SuFEx Ambiphiles: Interconversion to Amino\u2010sulfurdiimidoyl Fluorides"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3134-9366","authenticated-orcid":false,"given":"Kexin","family":"Su","sequence":"first","affiliation":[{"name":"Department of Chemistry Sustainable Chemistry for Metals and Molecules (SCM<sup>2<\/sup>), KU Leuven  Celestijnenlaan 200F box 2404 Leuven 3001 Belgium"},{"name":"Department of Chemistry Biomolecular Architecture, KU Leuven  Celestijnenlaan 200F box 2404 Leuven 3001 Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2186-5209","authenticated-orcid":false,"given":"Luc","family":"Van Meervelt","sequence":"additional","affiliation":[{"name":"Department of Chemistry Sustainable Chemistry for Metals and Molecules (SCM<sup>2<\/sup>), KU Leuven  Celestijnenlaan 200F box 2404 Leuven 3001 Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7400-1319","authenticated-orcid":false,"given":"Steven H. 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