Regioselective Pathway to Aniline Synthesis: Copper(II) Mediated Coupling of Saccharin with Arylboronic Acids
Dueweke, Ehren R.
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Anilines were synthesized in a novel reaction between copper(II) saccharin and various arylboronic acids. Reduction of copper(II) facilitated the formation of a carbon-nitrogen bond between each aryl group and a saccharin moiety. Saccharin was substituted on each aryl group at the carbon center to which the boronic acid substituent was initially bound, thus providing a regioselective means of synthesizing aryl saccharides. The effect of various aryl-chain substituents on the success of this reaction was examined. Aniline yields were greatest when the aryl group contained electron-withdrawing substituents at ortho or para positions with respect to the carbon reaction center, and likewise yields were lowest when that carbon atom was subject to donation of electron density by a substituent chain. The rate of the reaction was found to behave logarithmically, proceeding quickly at first but then becoming much slower for the bulk duration of the reaction. Data concerning the order of the reaction was also obtained and all reaction products were amply characterized.