N-Methyl-N-tosyl trifluoromethanesulfenamide

CAS 1045822-31-8, Cat. No EN300-258021
Reagent for trifluoromethylthiolation

EnamineStore

N-Methyl-N-tosyl trifluoromethanesulfenamide is a universal reagent for trifluoromethylthiolation of a broad scope of substrates^1,2. It is yellow solid, bench-stable, and soluble in alkanes, alcohols, diethyl ether, dichloromethane, DMF, and DMSO². The reagent reacts with heteroatomic nucleophiles, and organometallic reagents and can undergo aromatic electrophilic substitution with electron-rich aromatic and heteroaromatic compounds¹. Furthermore, terminal alkynes reacting with it in copper-catalyzed, base-free conditions to yield trifluoromethylthiolated alkynes or, if an electron-withdrawing substituent is present to yield vic-bistrifluoromethylthiolated vinylic products with (Z)-selectivity¹. The chemoselectivity of the reagent is controlled by the conditions of the reaction, which allows the usage of the reagent in the presence of many functional groups^{1, 2}. The obtaining of trifluoromethanesulfenamides, including late-stage functionalization of bioactive compounds under mild conditions with iodide catalysis, is also described³.

Synonyms: benzenesulfonamide, N,4-dimethyl-N- [(trifluoromethyl)thio]; N,4-dimethyl-N-[(trifluoromethyl)sulfanyl] benzene-1-sulfonamide; BB23