D. N. Tomilin, D. Yu. Soshnikov, A. B. Trofimov, M. D. Gotsko, L. N. Sobenina, I. A. Ushakov, A. V. Afonin, A. B. Koldobskii, N. M. Vitkovskaya, B. A. Trofimov, “Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight”, Mendeleev Commun., 2016, Volume 26, Issue 6,Pages <nobr>480

This article is cited in 11 papers

Communications

Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight

D. N. Tomilin^a, D. Yu. Soshnikov^ab, A. B. Trofimov^b, M. D. Gotsko^a, L. N. Sobenina^a, I. A. Ushakov^a, A. V. Afonin^a, A. B. Koldobskii^c, N. M. Vitkovskaya^b, B. A. Trofimov^a

^a A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation
^b Department of Chemistry, Irkutsk State University, Irkutsk, Russian Federation
^c A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation

Abstract: Cross-coupling of NH-pyrroles with 1-bromo-2-(trifluoroacetyl) acetylene in the Al₂O₃ medium affords (E)-4-bromo-1,1,1-trifluoro-4-(pyrrol-2-yl)but-3-en-2-ones instead of the expected 2-ethynylated products. Quantum-chemical analysis shows strong intramolecular hydrogen bonding between NH and trifluoroacetyl groups, higher NH acidity and deeper charge transfer to the ethenyl moiety, which determines the reaction pathway.

Language: English

DOI: 10.1016/j.mencom.2016.11.006

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