101327-89-3Relevant academic research and scientific papers
High yield direct fluorofunctionalisation of ketones using accufluor - NFTh fluorinating reagent
Stavber, Stojan,Zupan, Marko
, p. 3591 - 3594 (1996)
Direct regioselective conversion of a variety of cyclic and acyclic ketones to α-fluoroketones was achieved in high to excellent yield using 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate) [Accufluor - NFTh] in acetonitrile solution. Copyright
Micellar-system-mediated direct fluorination of ketones in water
Stavber, Gaj,Zupan, Marko,Stavber, Stojan
scheme or table, p. 589 - 594 (2009/07/09)
A micellar system was developed and applied for direct regioselective fluorination of a variety of cyclic and acyclic ketones to α-fluoroketones in water as reaction medium with Selectfluor F-TEDA-BF4 as fluorinating reagent. The inexpensive ionic amphiphile sodium dodecyl sulfate (SDS) was found to be an excellent promoter for fluorofunctionalization of hydrophobic ketones without prior activation or use of acid catalysts. Georg Thieme Verlag Stuttgart.
Direct electrophilic α-fluorination of imines: Efficient synthesis of mono-and difluoroimines
Verniest, Guido,Van Hende, Eva,Surmont, Riccardo,De Kimpe, Norbert
, p. 4767 - 4770 (2007/10/03)
(Chemical Equation Presented) A mild and efficient procedure to synthesize α-fluoro- and α,α-difluoroimines was developed. Various N-alkylimines derived from acetophenones were successfully monofluorinated using NFSI (N-fluorobenzenesulfonimide) in a mixture of CH3CN and DMF at 0°C. Alternatively, the same procedure without DMF gave rise to difluorinated imines when performed at room temperature. The obtained α- and α,α-difluorinated imines were subsequently reduced to give the corresponding β-fluoro- and β,β-difluoroamines in good yield.
Chelation-controlled diastereoselective reduction of α-fluoroketones
Mohanta, Pramod K.,Davis, Todd A.,Gooch, Jeremy R.,Flowers II, Robert A.
, p. 11896 - 11897 (2007/10/03)
The effect of Ti-based Lewis acids on the reduction of α-fluoropropiophenone was examined to determine whether chelation control could be used to direct the diastereoselectivity of conversion to an α-fluoro alcohol. Pretreatment of α-fluoropropiophenone with TiCl4 followed by reduction with LiBH4 in diethyl ether or methylene chloride provided the syn diastereomer predominantly, while use of Ti(OiPr)4 under identical conditions provided the anti diastereomer as the major product. The products are consistent with a chelation-controlled mechanistic pathway in the former reduction and a nonchelation pathway in the latter case. Detailed 1H, 13C, and 19F NMR studies were consistent with chelation between TiCl4 and α-fluoropropiophenone under the reaction conditions utilized in this study. Reduction of other α-fluoroketones in the presence of TiCl4 also provided a high degree of diastereoselectivity in the conversion to α-fluoro alcohols, showing the generality of this approach. Copyright
Preparation of alpha -fluoroketones
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, (2008/06/13)
PCT No. PCT/GB97/01547 Sec. 371 Date Feb. 5, 1998 Sec. 102(e) Date Feb. 5, 1998 PCT Filed Jun. 6, 1997 PCT Pub. No. WO97/46508 PCT Pub. Date Dec. 11, 1997The use of polar organic solvent as the solvent in the direct fluorination, to make an alpha -fluorok
