A Green, One-Pot Route to the Biphenyldicarboxylic Acids: Useful Intermediates in Polymer Synthesis

Richard S. Clary, Christopher D. Lee, William G. Monroe IV, David A. Vaughn, Ragy T. Ragheb, Jack W. Erter III, David M. Brown, David A. Schiraldi

Department of Chemistry, Davidson College, Davidson, NC, USA.
Department of Macromolecular Science & Engineering, Case Western Reserve University, Cleveland, OH, USA.

DOI: 10.4236/ijoc.2013.32016                

Abstract

Isomeric biphenyldicarboxylic acids have been prepared from halobenzoic acids and aryl boronic acids using an inverse biphasic modification of the Suzuki coupling reaction. In this modification of the Suzuki coupling reaction, both reactants and products are contained in the aqueous phase, with palladium catalyst contained in the organic phase. A phase transfer catalyst is used to contact reactants and catalyst. Multiple cycles, in which the catalyst/organic solvent is contacted with fresh aqueous reactants, generating products with no loss of efficiency, are demonstrated. We believe that this is the first demonstration of Suzuki coupling to produce biphenyldicarboxylic acids, in this case useful as monomers for the production of condensation polymers.

Keywords

Biphenyl; Carboxylic Acid; Suzuki

Conflicts of Interest

The authors declare no conflicts of interest.

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