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Pigulski B, Arendt A, Tomilin DN, et al. Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles. J Org Chem. 2016;81(19):9188-9198doi: 10.1021/acs.joc.6b01732.
Pigulski, B., Arendt, A., Tomilin, D. N., Sobenina, L. N., Trofimov, B. A., & Szafert, S. (2016). Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles. The Journal of organic chemistry, 81(19), 9188-9198. https://doi.org/10.1021/acs.joc.6b01732
Pigulski, Bartłomiej, et al. "Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles." The Journal of organic chemistry vol. 81,19 (2016): 9188-9198. doi: https://doi.org/10.1021/acs.joc.6b01732
Pigulski B, Arendt A, Tomilin DN, Sobenina LN, Trofimov BA, Szafert S. Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles. J Org Chem. 2016 Oct 07;81(19):9188-9198. doi: 10.1021/acs.joc.6b01732. Epub 2016 Sep 12. PMID: 27561913.
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J Org Chem. 2016 Oct 07;81(19):9188-9198. doi: 10.1021/acs.joc.6b01732. Epub 2016 Sep 12.

Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles.

The Journal of organic chemistry

Bartłomiej Pigulski, Agata Arendt, Denis N Tomilin, Lyubov N Sobenina, Boris A Trofimov, Sławomir Szafert

Affiliations

  1. Department of Chemistry, University of Wroc?aw , 14 F. Joliot-Curie, 50-383 Wroc?aw, Poland.
  2. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences , 1 Favorsky, 664033 Irkutsk, Russian Federation.

PMID: 27561913 DOI: 10.1021/acs.joc.6b01732

Abstract

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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