Categories: C-O Bond Formation >
Synthesis of Phenols
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Name Reactions
Sandmeyer-type Reaction
Recent Literature
The direct and selective palladium-catalyzed synthesis of phenols from aryl
halides and KOH has been achieved through the use of highly active
monophosphine-based catalysts and the biphasic solvent system 1,4-dioxane/H2O.
K. W. Anderson, T. Ikawa, R. E. Tundel, S. L. Buchwald, J. Am. Chem. Soc., 2006,
128, 10694-10695.
Various siletanes have been used as substrates for the oxidation of
carbon-silicon bonds upon exposure to aqueous fluoride and peroxide. These
tetraalkylsilanes offer a combination of stability and reactivity with many
practical benefits, including compatibility with silicon protecting groups
and electron-rich aromatic rings.
J. D. Sunderhaus, H. Lam, G. B. Dudley, Org. Lett.,
2003,
8, 4571-4573.
Nitroarenes react with anions of tert-butyl and cumyl
hydroperoxides in the presence of strong bases to form substituted o- and
p-nitrophenols. The reaction usually proceeds in high yields and is of
practical value as a method of synthesis and manufacturing of nitrophenols.
M. Makosza, K. Sienkiewicz, J. Org. Chem., 1998,
63, 4199-4208.
A palladium-catalyzed synthesis of aryl tert-butyl ethers from a
variety of unactivated aryl bromides or chlorides is described. The ether
products, which are precursors to phenols, are obtained in very good yield
in the presence of air-stable dialkylphosphinobiphenyl ligands.
C. A. Parrish, S. L. Buchwald, J. Org. Chem, 2001,
66, 2498-2500.
Various anilides have been directly ortho-acetoxylated with acetic acid as the acetate
source and K2S2O8 as the oxidant in the
presence of
Pd(OAc)2 as catalyst. The amide group is an elegant directing group to convert aromatic sp2 C-H bonds into C-O bonds.
G.-W. Wang, T.-T. Yuan, X.-L. Wu, J. Org. Chem., 2008,
73, 4717-4720.
Drawbacks associated with the classic Balz-Schiemann reaction are eliminated
in a series of examples by conducting fluorodediazoniation in ionic liquid
solvents.
K. K. Laali, V. J. Gettwert, J. Fluorine Chem., 2001,
107, 31-34.
