Reaction of indoles with aromatic fluoromethyl ketones: An efficient synthesis of trifluoromethyl-indolyl-phenylethanols using K2CO3/nBu4PBr in water

  1. Thanigaimalai PillaiyarORCID Logo,
  2. Masoud Sedaghati and
  3. Gregor Schnakenburg

Submitting author affiliation: Pharmaceutical institute, University of Bonn, Bonn, Germany

Beilstein Arch. 2020, 202017. https://doi.org/10.3762/bxiv.2020.17.v1

Published 12 Feb 2020

  • Preprint

Abstract

A new, mild and efficient protocol for the synthesis of trifluoromethyl-indolyl-phenylethanols by the reaction of indoles with a variety of aromatic fluoromethyl ketones in the presence of K2CO3 (15 mol%) and nBu4PBr (15 mol%) in water. The desired products were obtained in good to excellent yields without requiring the column chromatography purification. The reusability of the catalytic system and large-scale synthesis of indolyl-phenylethanols, which would further transform into biological active indole-derived compounds, are further advantages of this protocol. 

Keywords: Indole, Friedel-Crafts reaction, C-C-bond formation, C3-funtionalization of indole, indole-3-carbinol, diindolylmethane, recyclability and large-scale synthesis

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Pillaiyar, T.; Sedaghati, M.; Schnakenburg, G. Beilstein Arch. 2020, 202017. doi:10.3762/bxiv.2020.17.v1

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