Iodosobenzene Diacetate
Recent Literature
LiBr is an efficient catalyst for the dihydroxylation of alkenes to afford
either syn or anti diols with excellent diastereoselectivity
depending upon the use of NaIO4 or PhI(OAc)2 as the
oxidants.
L. Emmanuvel, T. M. A. Shaikh, A. Sudalai, Org. Lett.,
2005,
7, 5071-5074.
Pd-catalyzed selective oxidation of Boc-protected N-methylamines with
IOAc as the oxidant involves a Boc-directed C-H activation process.
D.-H. Wang, X.-S. Hao, D.-F. Wu, J.-Q. Yu, Org. Lett.,
2006,
8, 3387-3390.
Copper(II) trifluoromethanesulfonate catalyzed a mild amidation of cyclic ethers
with iminoiodanes with good yields and selectivity. A subsequent reductive
ring-opening of the tosylamidated products gives α,ϖ-amino alcohols.
L. He, J. Yu, J. Zhang, X.-Q. Yu, Org. Lett., 2007,
9, 2277-2280.
A new palladium-catalyzed method allows the oxygenation of unactivated sp3
C-H bonds of a wide variety of alkane substrates containing readily
available oxime and/or pyridine directing groups with extremely high levels
of chemo-, regio-, and in some cases diastereoselectivity.
L. V. Desai, K. L . Hull, M. S. Sanford, J. Am. Chem. Soc.,
2004,
126, 9542-9543.
A palladium-catalyzed intramolecular diamination reaction yields cyclic
ureas as direct products of an oxidative alkene transformation in the
presence of iodosobenzene diacetate as terminal oxidant.
J. Streuff, C. H. Hövelmann, M. Nieger, K. Muniz, J. Am. Chem. Soc.,
2005,
127, 14586-14587.
An intermolecular Pd-catalyzed aminoacetoxylation of alkenes with phthalimide
as the nitrogen source and PhI(OAc)2 as the stoichiometric oxidant
and source of acetate achieves a highly regio- and diastereoselective oxidative
1,2-difunctionalization of alkenes. The mechanism is discussed.
G. Liu, S. S. Stahl, J. Am. Chem. Soc.,
2006,
128, 7179-7181.
A catalytic Mitsunobu reaction system is described in which the azo reagent
is used as an organocatalyst and iodosobenzene diacetate is used as the
stoichiometric oxidant. Yields obtained in the catalytic reactions of carboxylic
acids and alcohols were slightly lower than those obtained from corresponding
stoichiometric reactions.
T. Y. S. But, P. H. Toy, J. Am. Chem. Soc., 2006,
128, 9636-9637.
A gold(I) compound, supported by 4,4',4' '-tri-tert-butyl-2,2':6',2' '-terpyridine
(tBu3tpy) as the ligand, efficiently catalyzes olefin
aziridination with the use of the commercially available oxidant PhI(OAc)2
and sulfonamides.
Z. Li, X. Ding, C. He, J. Org. Chem., 2006,
71, 5876-5880.
Various 2-arylbenzimidazoles were synthesized from phenylenediamines and
aldehydes via a one-step process using hypervalent iodine as oxidant. This
method features mild conditions, short reaction times, high yields, and a simple
procedure.
L-H. Du, Y.-G. Wang, Synthesis, 2007,
675-678.
2-Imidazolines were easily prepared in good yields from the reaction of
aldehydes and ethylenediamine with iodine in the presence of potassium carbonate.
The 2-imidazolines were smoothly oxidized to the corresponding imidazoles in
good yields using (diacetoxyiodo)benzene at room temperature.
M. Ishihara, H. Togo, Synlett,
2006, 227-230.
A new Pd-catalyzed oxidation reaction for the stereospecific conversion of
enynes into cyclopropyl ketones proceeds with net inversion of geometry with
respect to the starting olefin. This result is consistent with a mechanism in
which the key cyclopropane-forming step involves nucleophilic attack of a
tethered olefin onto the PdIV-C bond.
L. L. Welbes, T. W. Lyons, K. A. Cychosz, M. S. Sanford, J. Am. Chem. Soc., 2007,
129, 5836-5837.
