928048-13-9Relevant academic research and scientific papers
Electrophilic ipso-iodination of silylated arylboronic acids
Durka,Górka,Kurach,Luliński,Serwatowski
experimental part, p. 2635 - 2643 (2010/11/21)
Silylated functionalized arylboronic acids were converted into corresponding iodinated arylboronic acids in good yields via the electrophilic ipso-desilylation effected with iodine chloride in refluxing CHCl3. Disilylated arylboronic acids were susceptible to diiodination. In addition, the structural characterization and reactivity of a novel sterically hindered ortho-silylated diarylborinic ester were reported. The potential of selected iodinated phenylboronic acids as monomers for the Suzuki-Miyaura cross-coupling polymerization was demonstrated.
A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles
Lulinski, Sergiusz,Madura, Izabela,Serwatowski, Janusz,Szatylowicz, Halina,Zachara, Janusz
, p. 144 - 154 (2007/10/03)
Functionalized 2-formylphenylboronic acids undergo an unprecedented tautomeric rearrangement in solution to form corresponding 1,3-dihydro-1,3- dihydroxybenzo[c][2,1]oxaboroles. X-Ray analyses of selected examples revealed diverse solid-state molecular structures from a planar open form with a hydrogen-bonded carbonyl group (X = 3-F) through a twisted conformer showing a weak carbonyl-boron interaction (X = 3,5-Br2) to a cyclic oxaborole derivative (X = 3-Br). Variable-temperature 1H NMR spectroscopy was used to determine equilibrium constants as well as enthalpies and entropies of tautomerization in a mixed solvent [D6]acetone-D2O (95:5). A computational approach to the process by DFT (B3LYP) and MP2 methods has also been performed. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
