CAS 2762957-87-7, Cat. No EN300-37380850
Reagent for sulfonimidamide synthesis
![Sulfinylidene[tris(propan-2-yl)silyl] amine](/images/Reagents/EN300-37380850_Scherme.jpg)
Sulfinylidene[tris(propan-2-yl)silyl] amine is a versatile reagent for synthesizing sulfonimidamides via primary sulfinamides1,2. It enables the direct conversion of organometallic reagents (Grignard, organolithium, organozinc) into sulfinamides under mild conditions. These intermediates can be further oxidized to sulfonimidamides using hypervalent iodine and amines. The reagent is compatible with diverse nucleophiles, including aryl, alkyl, and heterocyclic compounds, making it valuable for pharmaceutical applications. It is a stable light-yellow liquid, remaining effective under refrigeration for at least a month. The efficiency and simplicity of the reagent's usage make it a powerful tool in medicinal and synthetic chemistry.
Synonyms: sulfinylidene[tris(propan-2-yl)silyl]amine; sulfinylidene[tris(propan-2-yl)silyl]amine; TIPS sulfinylidene amine
Selected publications
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Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides.
Ding M.; Zhang Z.-X.; Davies T. Q.; Willis M. C. A Org Lett 2022, 24 (8), 1711–1715. DOI: 10.1021/acs.orglett.2c00347
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Photocatalytic Carboxylate to Sulfinamide Switching Delivers a Divergent Synthesis of Sulfonamides and Sulfonimidamides.
Andrews J. A.; Kalepu J.; Palmer C. F.; Poole D. L.; Christensen K. E.; Willis M. C. J Am Chem Soc 2023, 145 (39), 21623–21629. DOI: 10.1021/jacs.3c07974