78181-02-9Relevant articles and documents
Iodination of organic substrates with halide salts and H2O2 using an organotelluride catalyst.
Higgs,Nelen,Detty
, p. 349 - 352 (2001)
[figure: see text] Organotelluride 1 is a water-soluble catalyst for the oxidation of iodide with hydrogen peroxide in pH 6 phosphate buffer. In two-phase systems, organic substrates are efficiently iodinated using 0.8 mol % of catalyst. Water-soluble substrates are iodinated without an organic cosolvent.
Imidazolium-containing diselenides for catalytic oxidations with hydrogen peroxide and sodium bromide in aqueous solutions
Alberto, Eduardo E.,Detty, Michael R.,Braga, Antonio L.
, p. 10476 - 10481,6 (2012/12/12)
The design and synthesis of imidazolium-containing diselenides 4a-c is described. The introduction of the N-methylimidazolium group gives freely soluble compounds in water, unlike the majority of common organic diselenides. Catalytic amounts of 4a-c effectively promote bromination of organic substrates using a safe and inexpensive NaBr/H2O2 system in water. Kinetics experiments revealed that the bromination of 4-pentenoic acid has a first-order dependence with respect to both NaBr and H2O2 concentrations The rate of reaction was also sensitive to the pH of the solution. Preparative reactions showed that, compared to 4a, diphenyl diselenide 5 was a poor catalyst and the ionic liquid 1-benzyl-3-methylimidazolium bromide 6 showed no catalytic activity with H2O2 indicating synergy from the combined functionality.
A xerogel-sequestered selenoxide catalyst for brominations with hydrogen peroxide and sodium bromide in an aqueous environment
Bennett, Stephanie M.,Tang, Ying,McMaster, Danielle,Bright, Frank V.,Detty, Michael R.
, p. 6849 - 6852 (2008/12/22)
(Chemical Equation Presented) 4-(Hydroxymethyl)phenyl benzyl selenoxide (4) sequestered in a halide-permeable, Class II xerogel formed from 10/90 (mol/mol) 3-aminopropyltriethoxysilane/tetraethoxysilane catalyzes the bromination of organic substrates (4-pentenoic acid, 3,5-dihydroxybenzoic acid, 1,3,5-trimethoxybenzene, N-phenylmorpholine, and N,N-dimethylaniline) with NaBr and H2O2. Catalyst performance (reaction rate) when sequestered within the halide-permeable xerogel is 23-fold greater in comparison to xerogel-free catalyst in solution. The catalyst is easily separated from the reaction mixture via filtration and the recovered catalyst can be reused without loss of activity through formation of the first 80 mol of product per mole of catalyst.
