One-pot synthesis of primary amino end-functionalized polymers by reaction of living anionic polybutadienes with nitriles

We present a convenient method to synthesize polymers with primary amino groups by end-capping of living anionic chain ends with nitriles followed by reduction in a one-pot process. As an example, the addition of pivalonitrile to the chain ends of oligobutadienyllithium in toluene, followed by the reduction with sodium borohydride quantitatively leads to ω-amino-oligo-1,4-butadiene, as demonstrated by 1H and 13C NMR, thin-layer chromatography and MALDI-ToF mass spectrometry.