Bis(2-methoxyethyl)aminosulfur Trifluoride:  A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability

Abstract

Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)2NSF3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C2H5)2NSF3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.

Synthesis and Anti-HIV Activity of New Metabolically Stable Alkenyldiarylmethane Non-Nucleoside Reverse Transcriptase Inhibitors Incorporating N-Methoxy Imidoyl Halide and 1,2,4-Oxadiazole Systems

“…19 F NMR spectra were obtained at 282 MHz in CDCl 3 , and chemical shifts are reported in δ values, relative to CF 3 CO 2 H at δ 0.00 ppm. IR spectra were recorded using a Perkin-Elmer 1600 series FT-IR.…”

Strategien zur Erforschung neuer Reaktionen

“…Zur Herstellung von Glycosylfluoriden [105] ist eine Vielzahl von Fluorierungsreagentien entwickelt worden, z. B. HF, [106] 2-Fluor-1-methylpyridiniumtosylat, [107] Diethylaminoschwefeltrifluorid (DAST), [108][109][110] HF/Pyridin, [111][112][113] CF 3 ZnBr/TiF 4 , [114] DEAD/PPh 3 /Et 3 O·BF 4 , [115] Selectfluor, [116] Deoxofluor, [117] N,N-Diisopropyl(1-fluor-2-methyl-1-propenyl)amin, [118] HF/MeCN/Ac 2 O, [119] AgF, [120] ZnF 2 , [121] Et 3 N-HF, [122] CF 3 ZnBr, [114] DAST/N-Bromsuccinimid(NBS)/N-Iodsuccinimid(NIS) [123,124] 4-Methyl(difluoriod)benzol, [125] TBAF [126] und PhI(OAc) 2 /SiF 4 . [127] Am häufigsten angewendet werden DAST, HF/Pyridin und DAST/NBS.…”

Fluorine is Flourishing in Pharmaceuticals

“…In recent years, fluorine chemistry has become a hot spot in chemical research due to its extensive application in pharmaceuticals. Breakthroughs in this field bring about several commercially available selective fluorination reagents, such as bis(2-methoxyethyl) aminosulfur trifluoride (Deoxofluor) [1], 1-chloromethyl-4-fluorodiazoniabicyclo [2,2,2] octane bis(tetrafluoroborate) (Selectfluor) [2], and N-fluorobenzenesulfonimide (NFSI) [3]. Among the fluorinated groups, trifluoromethyl is the most useful in pharmaceuticals.…”