IBX
2-Iodoxybenzoic acid (IBX), the impact-sensitive intermediate in the synthesis of the Dess-Martin periodinane, is available in a DMSO solution and is used as an oxidizing agent.
Recent Literature
A mild and efficient oxidation of alcohols with o-iodoxybenzoic acid
(IBX) is catalyzed by β-cyclodextrin in a water/acetone mixture (86:14).
Various alcohols were oxidized at room temperature in
excellent yields.
K. Surendra, N. Srilakshmi Krishnaveni, M. Arjun Reddy, Y. V. D. Nageswar, K.
Rama Rao, J. Org. Chem., 2003,
68, 2058-2059.
Alcohols are oxidized to the corresponding carbonyl compounds with iodoxybenzoic
acid (IBX) or with Dess-Martin-Periodinane (DMP) in hydrophilic [bmim]BF4
and hydrophobic [bmim]PF6 ionic liquids at room temperature under
mild conditions in excellent yields with high selectivity. IBX and DMP promoted
oxidations are faster in ionic liquids as compared to conventional solvents such
as DMSO, DMF, EtOAc and H2O. The byproduct iodosobenzoic acid (IBA)
and the ionic liquid are readily recovered.
J. S. Yadav, B. V. S. Reddy, A. K. Basak, A. V. Narsaiah, Tetrahedron,
2004,
60, 2131-2135.
A chemoselective oxidation of secondary alcohols with IBX/n-Bu4NBr
in CH2Cl2-H2O gave ketones in good yields and
allowed the oxidation of secondary hydroxyl group even in the presence of
primary hydroxyl groups.
C. Kuhakarn, K. Kittigowittana, M. Pohmakotr, V. Reutrakul, Tetrahedron, 2005,
61, 8995-9000.
Catalytic use of o-iodoxybenzoic acid (IBX) in the presence of
Oxone as a co-oxidant is demonstrated for the oxidation of primary and
secondary alcohols.
A. P. Thottumkara, M. S. Bowsher, T. K. Vinod, Org. Lett.,
2005,
7, 2933-2936.
o-Iodoxybenzoic acid (IBX) was found to be highly effective in
oxidations adjacent to carbonyl and benzylic functionalities to form
either α,β-unsaturated carbonyl compounds or conjugated aromatic
carbonyl systems. Fine-tuning of the reaction conditions allowed
remarkably selective transformations within multifunctional substrates.
K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem.
Soc., 2002,
124, 2245-2258.
K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem.
Soc., 2002,
124, 2245-2258.
K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem.
Soc., 2002,
124, 2245-2258.
A practical and environmentally friendly method for the oxidative
rearrangement of five- and six-membered cyclic tertiary allylic alcohols to
α,β-unsaturated β-disubstituted ketones by IBX in DMSO is described. Several
conventional protecting groups (e.g., Ac, MOM, and TBDPS) are tolerated.
M. Shibuya, S. Ito, M. Takahashi, Y. Iwabuchi, Org. Lett., 2004,
6, 4303-4306.
1,3-Diols undergo smooth oxidative cleavage of the C-C bond in the presence of
2-iodoxybenzoic acid (IBX) affording 1,2-diketones in excellent yields under
mild conditions.
J. S. Yadav, S. K. Biswas, R. Srinivas,
Synthesis, 2006, 4237-4241.
A clean and efficient method for the oxidative transformations of primary
carboxamides to one-carbon dehomologated nitriles using the combination of
o-iodoxybenzoic acid and tetraethylammonium bromide exhibits a broad scope and
is expected to be of great utility in organic synthesis.
D. S. Bhalarao, U. S. Mahajan, K. H. Chaudhari, K. G. Akamanchi, J. Org. Chem., 2007,
72, 662-665.
Different new reactions of IBX with heteroatom-containing substrates
were discovered and their utility was demonstrated. IBX was used for the
generation of imines from secondary amines in notably high yields, for
oxidative aromatization of nitrogen heterocycles and for cleavage of
dithianes.
K. C. Nicolaou, C. J. N. Mathison, T. Montagnon,
Angew. Chem., 2003, 115, 4211-4216.
K. C. Nicolaou, C. J. N. Mathison, T. Montagnon,
Angew. Chem., 2003, 115, 4211-4216.
K. C. Nicolaou, C. J. N. Mathison, T. Montagnon,
Angew. Chem., 2003, 115, 4211-4216.
K. C. Nicolaou, C. J. N. Mathison, T. Montagnon,
Angew. Chem., 2003, 115, 4211-4216.
IBX has been utilized in the oxidation of various epoxides and
aziridines, which gave for the first time α-hydroxyketones and
α-aminoketones. β-Cyclodextrin was used as the host for this
reaction, which was conducted in the environmentally friendly reaction
medium water.
K. Surendra, N. S. Krishnaveni, M. A. Reddy, Y. V. D. Nageswar, K. R.
Rao, J. Org. Chem., 2003, 68, 9119-9121.
The α-hydroxylation of α-alkynyl carbonyl compounds using IBX (o-iodoxybenzoic
acid) gave various α-hydroxyketones without dehydrogenation products
under mildly acidic conditions.
S. F. Kirsch, J. Org. Chem., 2005,
70, 10210-10212.
S. F. Kirsch, J. Org. Chem., 2005,
70, 10210-10212.
Hantzsch 1,4-dihydropyridines undergo smooth aromatization catalyzed by
iodoxybenzoic acid (IBX) to afford the corresponding pyridine
derivatives in high yields. All the reactions were carried out in DMSO
solvent at 80-85 °C for a period of two to four hours to complete
conversion of the substrates.
J. S. Yadav, B. V. S. Reddy, A. K. Basak, G. Baishya, A. V. Narsaiah,
Synthesis, 2006, 451-454.
Oximes of various aldehydes and ketones can be converted to the
corresponding carbonyl compounds at room temperature in excellent yields
with 2-iodylbenzoic acid in water in the presence of β-cyclodextrin.
N. S. Krishnaveni, K. Surendra, Y. V. D. Nageswar, K. R. Rao, Synthesis,
2003, 1968-1969.
An efficient and convenient procedure has been developed for the
hydrolysis of thioacetals/thioketals to the corresponding carbonyl
compounds in excellent yields with o-iodoxybenzoic acid (IBX) in
presence of β-cyclodextrin (β-CD) in water under neutral conditions at
room temperature.
N. S. Krishnaveni, K. Surendra, Y. V. D. Nageswar, K. R. Rao, Synthesis,
2003, 2295-2297.
