t-Butyl N-{[3,5-bis(trifluoromethyl)benzenesulfonyl]oxy}carbamate

CAS -, Cat. No EN300-52272785
Reagent for heterocycles skeletal editing

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t-Butyl N-{[3,5-bis(trifluoromethyl)benzenesulfonyl]oxy}carbamate is a novel reagent used for the regiocontrolled synthesis of polysubstituted N-alkylpyrazoles through skeletal single atom editing¹. The transformation starts with N-amination of isothiazoles, enabling the synthesis of 1,2,3-thiadiazine-S-oxides (TDSOs)¹. These intermediates undergo ring expansion and SO extrusion to afford unsymmetrical N-alkyl pyrazoles with high regioselectivity. The reagent generates an electrophilic NH₂⁺ species in situ, making it effective even with poorly nucleophilic substrates. It is bench-stable, scalable, and synthesized efficiently on a 100 mmol scale. This approach provides a powerful strategy for regiocontrolled pyrazole synthesis and the selective late-stage functionalization of heterocycles.

Synonyms: tert‐butyl N‐{[3,5‐bis(trifluoromethyl)benzenesulfonyl]oxy}carbamate; tert-butyl N-((3,5-bis(trifluoromethyl)phenyl)sulfonyl)oxycarbamate; N-Boc-O-(3,5-bistrifluoromethylphenyl)sulfonyl-hydroxylamine