E. Yu. Schmidt, N. V. Semenova, E. V. Ivanova, I. A. Bidusenko, B. A. Trofimov, “Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles”, Mendeleev Commun., 2020, Volume 30, Issue 1,Pages <nobr>109

This article is cited in 15 papers

Communications

Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles

E. Yu. Schmidt^ab, N. V. Semenova^a, E. V. Ivanova^a, I. A. Bidusenko^a, B. A. Trofimov^a

^a A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation
^b Angarsk State Technical University, Angarsk, Russian Federation

Abstract: A new superbase-promoted reaction of acetylene involves self-organization of its three molecules with one molecule of arylamine in KOH/DMSO system to afford 1-aryl-2,5- dimethylpyrroles in up to 63% yields. The key step of this reaction cascade is assumed to be the nucleophilic addition of acetylene to the C=N bond of the intermediate aldimine (aza-Favorsky reaction).

Keywords: acetylene, arylamines, imines, pyrroles, superbases, vinylation, ethynylation..

Language: English

DOI: 10.1016/j.mencom.2020.01.036

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