Iodosylbenzene
Recent Literature
A rapid oxidation of primary and secondary alcohols using catalytic amounts of
TEMPO and Yb(OTf)3 in combination with a stoichiometric amount of
iodosylbenzene afforded carbonyl compounds in excellent yields without
over-oxidation. Oxidation of primary alcohols in the presence of secondary
alcohols proceeded with good selectivity.
J.-M. Vatèle, Synlett, 2006,
2055-2058.
A sequential one-pot synthesis for the oxidation of primary and secondary
tert-butyldimethylsilyl (TBDMS) ethers, using the presence of PhIO or
PhI(OAc)2 and catalytic amounts of metal triflates and TEMPO in THF
or acetonitrile tolerates acid-sensitive protecting groups and leaves tert-butyldiphenylsilyl
ethers and phenolic TBDMS groups untouched.
B. Barnych, J.-M. Vatèle, Synlett, 2011,
2048-2052.
α-Tosyloxyketones and α-tosyloxyaldehydes were directly prepared from alcohols by treatment
with iodosylbenzene and p-toluenesulfonic acid monohydrate in
good yields. Modified methods gave thiazoles, imidazoles and
imidazo[1,2-a]pyridines from alcohols in good to moderate yields.
M. Ueno, T. Nabana, H. Togo, J. Org. Chem.,
2003, 68, 6424-6426.
The use of iodosobenzene (PhIO) as oxidant and p-toluenesulfonamide (TsNH2)
as aminating reagent in the presence of a catalytic amount of perchlorate zinc
hexahydrate enables a direct α-amination of β-dicarbonyl compounds. The reaction
proceeds quickly at rt to provide the corresponding α-N-tosylamido
β-dicarbonyl compounds very good yields.
J. Yu, S.-S. Liu, J. Cui, X.-S. Hou, C. Zhang, Org. Lett., 2012,
14, 832-835.
A palladium-catalyzed dimerization of terminal acetylenes with iodosylbenzene as
oxidant allowed the preparation of various diynes in good yields in a short
period of time at room temperature.
J. Yan, F. Lin, Z. Yang, Synthesis, 2007,
1301-1303.
An efficient solvent-controlled oxidative cyclization of Michael adducts of
malonates with chalcones with the combination of iodosobenzene and
tetrabutylammonium iodide enables the divergent synthesis of highly
functionalized oxetanes and cyclopropanes in good yields with high
diastereoselectivity.
Y. Ye, C. Zheng, R. Fan, Org. Lett., 2009,
11, 3156-3159.
Y. Ye, C. Zheng, R. Fan, Org. Lett., 2009,
11, 3156-3159.
M. Ueno, T. Nabana, H. Togo, J. Org. Chem.,
2003, 68, 6424-6426.
M. Ueno, T. Nabana, H. Togo, J. Org. Chem.,
2003, 68, 6424-6426.
