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.
A highly efficient direct α-acyloxylation of 1,3-dicarbonyl compounds with
carboxylic acids is mediated by iodosobenzene. The reaction of various
1,3-dicarbonyl compounds with carboxylic acids provides the corresponding
α-acyloxylated products in good to excellent yields under mild reaction
conditions. The loading sequence of reactants and oxidant is crucial for the
generation of the active species.
C. B. Rao, J. Yuan, Q. Zhang, R. Zhang, N. Zhang, J. Fang, D. Dong, J. Org. Chem., 2018, 83,
2904-2911.
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.
N-Triflylimino-λ3-iodanes, which can be generated in situ
from iodosylarene and triflylamide, can be used for imidations of phosphines and
α-amidations of 1,3-dicarbonyl compounds without any other additives. The
imino-λ3-iodanes can also be catalytically generated from an
iodoarene precatalyst with oxone and triflylamide.
S. Sunagawa, F. Morisaki, T. Baba, A. Tsubouchi, A. Yoshimura, K. Miyamoto,
M. Uchiyama, A. Saito, Org. Lett.,
2022, 24, 5230-5234.
A direct copper-catalyzed nitrogen transfer is mediated by the powerful oxygen
atom donor PhI=O. This unique reaction greatly simplifies the procedure for
copper-catalyzed aziridination of olefins and enhances its efficiency.
P. Dauban, L. Sanière, A. Tarrade, R. H. Dodd, J. Am. Chem. Soc., 2001,
123, 7707-7708.
The direct fluorination reaction of acetophenone derivatives, acetonaphthones,
benzyl phenyl ketone, propiophenone, butyrophenone, 1-indanone, and phenacyl
chloride using iodosylarenes and TEA·5HF gives the corresponding α-fluoroketone
derivatives in good yields under mild conditions except for use of a HF reagent.
T. Kitamura, K. Muta, K. Muta, J. Org. Chem., 2014,
79, 5842-5846.
The combination of PhIO and HF·py enables fluorination of functionalized
aromatic olefins bearing synthetically important carbonyl and hydroxyl groups.
Fluorination of for example 1,3-diphenyl-2-propen-1-one with PhIO/HF·py reagent
gave 3,3-difluoro-1,2-diphenyl-1-propanone in high yield. The fluorination of
cinnamyl alcohol derivatives proceeded smoothly to afford
2-aryl-3,3-difluoro-1-propanols in moderate yields.
T. Kitamura, K. Yoshida, S. Mizuno, A. Miyake, J. Oyamada, J. Org. Chem., 2018, 83,
14834-14841.
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.
