BTSF

CAS 368-65-0, Cat. No EN300-52136758
Reagent for SuFEx deoxyazidation

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1,3,5-Benzenetrisulfonyl trifluoride (BTSF) is a stable trifunctional sulfonyl fluoride reagent developed for the efficient deoxyazidation of primary and secondary alcohols through sulfur(VI) fluoride exchange (SuFEx) chemistry¹ (similar reagent EN300-727934). In combination with trimethylsilyl azide (TMSN₃) and DBU in acetonitrile, BTSF enables the direct conversion of alcohols into organic azides under mild conditions at room temperature. Owing to its three reactive sulfonyl fluoride groups, the reagent can be employed at only 0.4 equivalents, providing 91% isolated yield in a model reaction and demonstrating excellent reagent economy. The methodology exhibits broad substrate scope and functional-group tolerance, including esters, ketones, alkenes, alkynes, amides, carbamates, sulfonamides, and heterocycles, and is applicable to structurally complex pharmaceutical derivatives. The reaction proceeds via initial SuFEx-mediated formation of sulfonate intermediates, followed by nucleophilic substitution with an azide, thereby allowing stereochemical inversion at suitable chiral alcohol centers. The resulting organic azides are valuable intermediates for Cu-catalyzed azide–alkyne cycloaddition (CuAAC), enabling the synthesis of triazole derivatives and late-stage diversification of drug-like molecules.

Synonyms: benzene-1,3,5-trisulfonyl trifluoride; benzene-1,3,5-trisulfonyl fluoride; BTSF