TITLE:
A Green, One-Pot Route to the Biphenyldicarboxylic Acids: Useful Intermediates in Polymer Synthesis
AUTHORS:
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
KEYWORDS:
Biphenyl; Carboxylic Acid; Suzuki
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.3 No.2,
June
14,
2013
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.