361-80-8Relevant academic research and scientific papers
PyFluor: A low-cost, stable, and selective deoxyfluorination reagent
Nielsen, Matthew K.,Ugaz, Christian R.,Li, Wenping,Doyle, Abigail G.
supporting information, p. 9571 - 9574 (2015/08/18)
We report an inexpensive, thermally stable deoxyfluorination reagent that fluorinates a broad range of alcohols without substantial formation of elimination side products. This combination of selectivity, safety, and economic viability enables deoxyfluorination on preparatory scale. We employ the [18F]-labeled reagent in the first example of a no-carrier-added deoxy-radiofluorination.
Synthesis of fluorinated steroids using a novel fluorinating reagent tetrabutylammonium difluorodimethylphenylsilicate (TAMPS)
Herrmann, Pavel,Kvicala, Jaroslav,Pouzar, Vladimir,Chodounska, Hana
experimental part, p. 1825 - 1834 (2009/06/19)
Steroidal 3-fluoroderivatives were prepared from corresponding tosylates using tetrabutyl-ammonium difluorodimethylphenylsilicate as fluorinating agent. The reaction was tested on all four possible C-3 and C-5 stereoisomers of cholestane and 17-oxoandrostane skeletons. In this reaction only one isomer was always formed with opposite configuration at C-3 to starting tosylate. The reaction is accompanied by elimination which affords a mixture of corresponding olefines.
Preparation of 3,17- and 3,20-difluoro-derivatives of the androst-5-ene and pregn-5-ene series
Decreau, Richard A.,Marson, Charles M.
, p. 4369 - 4385 (2007/10/03)
Unsaturated mono- and difluorosteroids have been prepared in high yield using n-perfluorobutanesulfonyl fluoride 1. The 3,17- and 3,20-difluoro-5,6- dehydrosteroids are reported for the first time. 3-Fluoroderivatives of the androst-5-ene-17-one and 5α-an
Fluorination of secondary and primary alcohols by thermal decomposition of electrochemically generated alkoxy triphenylphosphonium tetrafluoroborates
Maeda, Hatsuo,Koide, Takashi,Matsumoto, Sayaka,Ohmori, Hidenobu
, p. 1480 - 1483 (2007/10/03)
Replacement of hydroxyl groups in secondary and primary alcohols (1) with a fluorine atom arising from tetrafluoroborate anion has been performed by the electrochemical formation of alkoxy triphenylphosphonium tetrafluoroborates (2) from 1, followed by their thermal decomposition. The procedure is quite simple, involving: (1) constant-current electrolysis of a mixture of 1, Ph3P, and Ph3PH·BF4 in CH2Cl2 in an undivided cell; (2) refluxing a tetrahydrofuran or dioxane solution of the residue afforded by evaporation of the solvent in vacuo after the electrolysis. Cyclic secondary alcohols such as 3β-hydroxy steroids and 2-adamantanol are transformed into the corresponding fluorides in satisfactory yields when the geometry of the leaving group in 2 is suitable for the substitution or an elimination process for 2 to give an alkene is stereochemically forbidden. The fluorination of steroidal alcohols and 4-phenyl-1-cyclohexanol proceeded with complete inversion, demonstrating that a fluorine atom from the tetrafluoroborate anion attacks from the side opposite to the phosphonium moiety in 2 via an SN2 mechanism rather than an SN1 mechanism. The fluorination of acyclic secondary and primary alcohols was performed by the present method in reasonable yields, although the reaction for the latter required more forcing conditions, such as refluxing in dioxane.
