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

2019; Wiley; Volume: 25; Issue: 30 Linguagem: Inglês

10.1002/chem.201901176

1521-3765

Junkai Guo, Cuiwen Kuang, Jian Rong, Lingchun Li, Chuanfa Ni, Jinbo Hu,

Chemical Synthesis and Reactions

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.