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Updated: May 10, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
1-Ethyl-2-phenyl-3-[2-(tri-methyl-sil-yl)ethyn-yl]-1H-indole
Iaroslav Baglai1, Valérie Maraval, Carine Duhayon
1Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska 64, 01033 Kyiv, Ukraine.
Abstract:
The title compound, C21H23NSi, was synthesized by Sonogashira-type reaction of 1-ethyl-3-iodo-2-phenyl-1H-indole with tri-methyl-silyl-acetyl-ene. The indole ring system is nearly planar [maximum atomic deviation = 0.0244 (15) Å] and is oriented at a dihedral angle of 51.48 (4)° with respect to the phenyl ring. The supramolecular aggregation is completed by weak C-H⋯π inter-actions of the methylene and phenyl groups with the benzene and pyrrole rings of the indole ring system. The methyl groups of the tri-methyl-silyl unit are equally disordered over two sets of sites.
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