Periodic Acid
Recent Literature
Benzyl alcohols and benzyl TBDMS ethers were efficiently oxidized to the
corresponding carbonyl compounds in high yield with periodic acid catalyzed
by CrO3 at low temperature (-78 °C). The oxidation procedure was
highly functional group tolerant and very selective for the TBDMS group over
the TBDPS group.
S. Zhang, L. Xu, M. L. Trudell, Synthesis, 2005, 1757-1760.
S. Zhang, L. Xu, M. L. Trudell, Synthesis, 2005,
1757-1760.
Oxidation of primary and secondary alcohols, using catalytic amounts of TEMPO
and tetra-n-butylammonium bromide in combination with periodic acid and
wet alumina in dichloromethane is compatible with a broad range of functional
groups and acid-sensitive protecting groups. The system also enables a
chemoselective oxidation of secondary alcohols in the presence of primary
alcohols.
M. Attoui, J.-M. Vatèle,
Synlett, 2014, 25, 2923-2927.
CrO3 is an efficient catalyst for benzylic oxidation with periodic
acid as the terminal oxidant in acetonitrile. Substituted electron-poor toluenes
and diarylmethanes were oxidized to the corresponding substituted benzoic acids
and ketones in excellent yields. Benzyl ethers such as isochroman and phthalan
were converted to 3,4-dihydroisocoumarin and phthalide in quantitative yields.
S. Yamazaki,
Org. Lett., 1999, 1, 2129-2132.
A CrO3-catalyzed oxidation of primary alcohols to carboxylic acids
proceeds smoothly with only 1-2 mol % of CrO3 and 2.5 equivalents of
H5IO6 in wet MeCN to give the carboxylic acids in
excellent yield. No significant racemization is observed for alcohols with
adjacent chiral centers. Secondary alcohols are cleanly oxidized to ketones.
M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J. J. Grabowski, P. J.
Reider, Tetrahedron Lett., 1998,
39, 5323-5326.
A facile and quantitative preparation of carboxylic acids by a
pyridinium chlorochromate (PCC) catalyzed (2 mol%) oxidation of primary
alcohols and aldehydes using 2.2 equivalents and 1.1 equivalents of H5IO6,
respectively, in acetonitrile is described here.
M. Hunsen,
Synthesis, 2005, 2487-2490.
A facile and quantitative preparation of carboxylic acids by a
pyridinium chlorochromate (PCC) catalyzed (2 mol%) oxidation of primary
alcohols and aldehydes using 2.2 equivalents and 1.1 equivalents of H5IO6,
respectively, in acetonitrile is described here.
M. Hunsen, Synthesis, 2005, 2487-2490.
Cp*Ir complexes bearing a chiral N-(2-picolyl)sulfonamidato catalyze a
convenient asymmetric reductive amination of benzylic ketones using readily
available β-amino alcohols as chiral aminating agents. The amino alcohol-derived
chiral auxiliary was easily removed by mild periodic oxidants, leading to
optically active primary β-arylamines without erosion of the optical purity.
T. Kawada, K. Yabushita, T. Yasuda, T. Ohta, T. Yajima, K. Tanaka, N. Utsumi, M.
Watanabe, K. Murata, Y. Kayaki, S. Kuwata, T. Katayama, J. Org. Chem., 2022, 87,
8458-8468.
CrO3 is an efficient catalyst for benzylic oxidation with periodic
acid as the terminal oxidant in acetonitrile. Substituted electron-poor toluenes
and diarylmethanes were oxidized to the corresponding substituted benzoic acids
and ketones in excellent yields. Benzyl ethers such as isochroman and phthalan
were converted to 3,4-dihydroisocoumarin and phthalide in quantitative yields.
S. Yamazaki,
Org. Lett., 1999, 1, 2129-2132.
An excellent method for the selective oxidation of sulfides to
sulfoxides with periodic acid (H5IO6) catalyzed by
FeCl3 in MeCN has been devised. The reported procedure is
fast, simple and the yields are excellent in most cases with reaction
time of less than 2 minutes.
S. S. Kim, K. Nehru, S. S. Kim, D. W. Kim, H. C. Jung, Synthesis, 2002, 2484-2486.
Bromination of alkenes, alkynes, and anilines has efficiently been carried out
at room temperature in short reaction times using potassium bromide and
orthoperiodic acid in dichloromethane-water (1:1) to prepare the corresponding
brominated compounds with excellent yields.
A. Khazaei, M. A. Zolfigol, E. Kolvari, N. Koukabia, H. Soltania, F. Komakia, Synthesis, 2009,
3672-3676.
