Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles
2016
Pigulski, Bartłomiej | Arendt, Agata | Tomilin, Denis N. | Sobenina, Lyubov N. | Trofimov, Boris A. | Szafert, Sławomir
In this contribution, the synthesis of long chain hexatriynyl- and octatetraynyl-substituted pyrroles in one step from 1-halopolyyne precursors is reported. The products were obtained via a mechanochemical approach by simple grinding of 1-haloalkynes with N-substituted pyrroles and potassium carbonate which played a role of heterogeneous catalyst and this solvent- and transition metal-free approach is unprecedent in the synthesis of new, organic, long chain polyynes. Additionally, an extensive X-ray single crystal study of pyrrole end-capped polyynes is presented. Such compounds are possible substrates for different oligoheterocycles and have a significant application potential such as for instance molecular wires.
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