Categories: C-F Bond Formation >
Synthesis of fluoroketones and fluoroaldehydes
Recent Literature
Catalytic enantioselective fluorination and chlorination reactions of
carbonyl compounds were achieved with high enantioselectivity by the use of
a dbfox-NiII complex.
N. Shibata, J. Kohno, K. Takai, T. Ishimaru, S. Nakamura, T. Toru, S.
Kanemasa, Angew. Chem. Int. Ed., 2005,
44, 4204-4207.
The use of 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane
bis(tetrafluoroborate) (Accufluor NFTh) as a fluorine transfer reagent and
methanol as solvent enabled direct regiospecific fluorofunctionalization of
the α-carbonyl position in ketones without prior activation of the target
molecules.
S. Stavber, M. Jereb, M. Zupan, Synthesis,
2002, 2609-2615.
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.
A desulfurizing difluorination reaction of benzyl sulfides having an
electron-withdrawing group such as an ester, a ketone, a nitrile, or an amide in
the presence of IF5 gave gem-difluoro compounds in good yield.
T. Fukuhara, S. Hara, Synlett, 2009,
198-200.
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.
W. Peng, J. M. Shreeve, J. Org. Chem., 2005,
70, 5760-5763.
W. Peng, J. M. Shreeve, J. Org. Chem., 2005,
70, 5760-5763.
