Selectfluor, Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), F-TEDA-BF4
Recent Literature
A micellar system was developed and applied for direct regioselective
fluorination of various 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.
G. Stavber, M. Zupan, S. Stavber, Synlett, 2009,
589-594.
Allylic alcohols are isomerized into enolates (enols) by [Cp*IrCl2]2.
A subsequent reaction with Selectfluor present in the reaction media produces
α-fluoro ketones as single constitutional isomers in good yields.
N. Ahlsten, A. Bartoszewicz, S. Agrawal, B. Martín-Matute, Synthesis, 2011,
2600-2608.
Reactions of enamines with Selectfluor under mild conditions easily led to
the corresponding difluorinated carbonyl compounds in high yields.
W. Peng, J. M. Shreeve, J. Org. Chem., 2005,
70, 5760-5763.
Selective introduction of an iodine atom at the α-carbonyl position in various
aryl alkyl ketones was effectively achieved by reaction of target molecules with
elemental iodine in the presence of N-F reagents such as F-TEDA-BF4 (Selectfluor)
as iodination mediators and methanol as the solvent.
M. Jereb, S. Stavber, M. Zupan, Synthesis,
2003, 853-858.
Benzene derivatives bearing at least one bulky alkyl group (i-Pr or
t-Bu) were selectively and effectively iodinated using elemental iodine
activated by Selectfluor. Up to three iodine atoms were progressively introduced
at the most electron-rich and sterically less hindered position on the benzene
ring.
S. Stavber, P. Kralj, M. Zupan, Synthesis,
2002, 1513-1518.
Using commercially available Ph3PAuCl and readily prepared, benign
arylsilanes, a gold-catalyzed oxyarylation of alkenes proceeds smoothly in air.
The oxidant, Selectfluor, not only facilitates entry to the Au(I/III) manifold
but also provides a fluoride anion for silane activation, thereby avoiding the
need for addition of a stoichiometric base.
L. T. Ball, M. Green G. C. Lloyd-Jones, C. A. Russel, Org. Lett., 2010,
12, 4724-4727.
Oxidative bromination of different types of olefins
using Selectfluor/KBr afforded addition, monobromo-substituted, or
Hunsdiecker-Borodin reaction products in good yields.
C. Ye, J. M. Shreeve, J. Org. Chem.,
2004,
69, 8561-8563.
Oxidative bromination of different types of olefins
using Selectfluor/KBr afforded addition, monobromo-substituted, or
Hunsdiecker-Borodin reaction products in good yields.
C. Ye, J. M. Shreeve, J. Org. Chem.,
2004, 69, 8561-8563.
