Carbon-carbon bond forming reactions using polymer supported reagents

ORGN 554

Paul A Boguszewski1, Andrew F Coffey1, John W Davies1, Alasdair A MacDonald2, Aubrey J Mendonca3, and Frank P Warner1. (1) Polymer Laboratories Ltd, Essex Road, Church Stretton, Shropshire, SY6 6AX, United Kingdom, (2) Polymer Laboratorie Inc, Amherst Fields Research Park, 160 Old Farm Road, Amherst, MA 01002, (3) Polymer Laboratories Inc, Amherst Fields Research Park, 160 Old Farm Road, Amherst, MA 01002
The carbon-carbon bond forming reaction is one of the most synthetically useful reactions employed in high throughput experimentation, providing an efficient means for increasing diversity. There are a wide variety of named reactions which frequently utilize triphenylphosphine (TPP) to effect the transformation (eg cross coupling), either directly or as a means of immobilizing a palladium, nickel or ruthenium catalyst. In solution phase, the use of TPP presents a problem for purification of the target compound whereby its by-product, triphenylphosphine oxide, is difficult to remove. However, by creating the polymer supported equivalent from p-styryldiphenylphosphine, removal of both species can be simultaneously achieved by simple filtration. By using copolymerization, the stoichiometry of the polymer supported TPP can be precisely controlled giving a highly reproducible product, free from contaminants resulting in a homogeneous environment for consistent results.