I. A. Bidusenko, E. Yu. Schmidt, N. I. Protsuk, I. A. Ushakov, B. A. Trofimov, “Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes”, Mendeleev Commun., 2023, Volume 33, Issue 1,Pages 24

This article is cited in 7 papers

Communications

Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes

I. A. Bidusenko, E. Yu. Schmidt, N. I. Protsuk, I. A. Ushakov, B. A. Trofimov

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation

Abstract: N-Benzyl aldimines react with arylacetylenes in the presence of Bu^tOK/DMSO superbase system to afford 2,3,5-triaryl-1-pyrrolines as two tautomers with 1,2- and 1,5-location of the double bond, both being the trans-diastereomers. This version of the C=N bond ethynylation differs from the previous one with N-benzyl ketimines. The oxidation of the pyrroline tautomeric mixtures without their isolation gives 2,3,5-triaryl-1H-pyrroles.

Keywords: acetylenes, imines, superbases, ethynylation, vinylation, pyrroles, pyrrolines.

Language: English

DOI: 10.1016/j.mencom.2023.01.007

	*Supplementary materials:*
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