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.
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.
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.
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.