Synfacts 2016; 12(12): 1245
DOI: 10.1055/s-0036-1589673
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Mechanochemical Synthesis of Pyrrole-Substituted Polyynes

Timothy M. Swager
Cagatay Dengiz
Pigulski B, Arendt A, Tomilin DN, Sobenina LN, Trofimov BA, Szafert S * University of Wrocław, Poland and A. E. Favorsky Irkutsk Institute of Chemistry, Russian Federation
Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles.

J. Org. Chem. 2016;
81: 9188-9198
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Publication History

Publication Date:
17 November 2016 (online)



The authors present a metal-free, mechanochemical synthesis of polyyne-substituted pyrroles. The structurally demanding hexatriynyl- and octatetraynyl-substituted pyrroles were successfully obtained by simple grinding of 1-haloalkynes, pyrroles, and potassium carbonate. This approach is unprecedented in the synthesis of long polyynes.



The reported synthesis exhibits an effective way to obtain pyrrole-end-capped polyynes. Although coupling reactions of pyrroles with 1-haloalkynes are much more efficient using bromides rather than iodides, 1-iodoalkynes were used for the synthesis of longer polyynes in this work because of the poor stability of longer 1-bromoalkynes. The presented polyynes are promising candidates for molecular wire applications.