342401-19-8

Upstream product

• 2901-92-0 p-chlorophenylsulfinyl chloride 
• 93-97-0 benzoic acid anhydride 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 16096-86-9 p-chlorobenzenesulphinamide 

Downstream Products

• 1264737-60-1 N-benzoyl-4-chlorophenyl sulfonimidoyl fluoride 
• 1264737-72-5 N-[(4-chlorophenyl)-oxo-(trifluoromethyl)-λ6-sulfanylidene]benzamide 
• 731-17-9 N-Benzoyl-p-chlorbenzolsulfonimidoylchlorid 

Relevant academic research and scientific papers

Rapid Deoxyfluorination of Alcohols with N-Tosyl-4-chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature

The deoxyfluorination of alcohols is a fundamentally important approach to access alkyl fluorides, and thus the development of shelf-stable, easy-to-handle, fluorine-economical, and highly selective deoxyfluorination reagents is highly desired. This work describes the development of a crystalline compound, N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor), as a novel deoxyfluorination reagent that possesses all of the aforementioned merits, which is rare in the arena of deoxyfluorination. Endowed by the multi-dimensional modulating ability of the sulfonimidoyl group, SulfoxFluor is superior to 2-pyridinesulfonyl fluoride (PyFluor) in fluorination rate, and is also superior to perfluorobutanesulfonyl fluoride (PBSF) in fluorine-economy. Its reaction with alcohols not only tolerates a wide range of functionalities including the more sterically hindered alcoholic hydroxyl groups, but also exhibits high fluorination/elimination selectivity. Because SulfoxFluor can be easily prepared from inexpensive materials and can be safely handled without special techniques, it promises to serve as a practical deoxyfluorination reagent for the synthesis of various alkyl fluorides.

Synthesis of CF3-substituted sulfoximines from sulfonimidoyl fluorides

N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert-Prakash reagent (TMSCF3) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed following two synthetic routes, and for each reaction sequence the substrate scope was evaluated. Accordingly, a wide variety of aryl-substituted products were obtained in moderate to good yield.