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.
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.