57504-59-3Relevant academic research and scientific papers
Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents
Malmedy, Florence,Wirth, Thomas
supporting information, p. 16072 - 16077 (2016/10/30)
The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.
Various α-oxygen functionalizations of β-dicarbonyl compounds mediated by the hypervalent iodine(III) reagent p-iodotoluene difluoride with different oxygen-containing nucleophiles
Jun, Yu,Jun, Tian,Chi, Zhang
experimental part, p. 531 - 546 (2010/06/13)
p-Iodotoluene difluoride (p-Tol-IF2) has been found to be a general reagent for the effective introduction of various oxygen-containing functionalities including tosyloxy, mesyloxy, acetoxy, phosphoryloxy, methoxy, ethoxy and isopropoxy at the α-position of β-dicarbonyl compounds. These transformations can be readily realized by the use of the combined reagent of p-iodotoluene difluoride and various oxygen-containing nucleophilic compounds such as p-toluenesulfonic acid, methanesulfonic acid, acetic acid, diphenyl phosphate, methanol, ethanol and propan-2-ol under mild conditions, respectively. And, the in situ generated hypervalent iodine(III) species via ligand exchange between p-iodotoluene difluoride and the respective oxygen-containing nucleophiles are believed to be the real oxidizing agents in such transformations.
Hypervalent Iodine Oxidation: α-Functionalization of β-Dicarbonyl Compounds Using Iodosobenzene
Moriarty, Robert, M.,Vaid, Radhe K.,Ravikumar, Vasulinga T.,Vaid, Beena K.,Hopkins, Thomas E.
, p. 1603 - 1608 (2007/10/02)
Hypervalent iodine oxidation of β-diketones and β-ketoesters with iodosobenzene-boron trifluoride etherate in chloroform using appropriate nucleophiles results in α-functionalization.Benzoylacetone on reaction with iodosobenzene or iodosobenzene boron trifluoride-etherate in methanol yields α-methoxyacetophenone (9) and methyl phenylacetate (10).The possible mechanisms for these reactions are discussed.
