Synthesis of novel nitrogen-containing polymers by Pd(0)-catalyzed polycondensation of propargylic carbonates and bifunctional nitrogen nucleophiles

A Pd(0)-catalyzed polycondensation of propargylic carbonates and bifunctional nitrogen nucleophiles was investigated. The polycondensation was carried out in THF at 80 degrees C for 20 h in the presence of a Pd(0) catalyst. The Pd(0)-catalyzed polycondensation with bifunctional nitrogen nucleophiles proceeded successfully when bis[(2-diphenylphosphino)phenyl]ether (DPEphos) was used as the ligand. N-monoalkylated bifunctional benzenesulfonamides and pyromellitic diimide could be used in the polycondensation. Aliphatic and aromatic amines did not afford the corresponding polymers at all. The molecular weights of the obtained polymers were higher when propargylic carbonates having an aryl group on the acetylenic terminal carbon were used. (C) 2011 Elsevier Ltd. All rights reserved.