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Facile Amberlyst A-21 catalyzed access of β-hydroxynitriles via epoxide opening in water

  • M. Shaheer Malik
  • , Basim H. Asghar
  • , Shaik Azeeza
  • , Rami J. Obaid
  • , Ismail I. Thagafi
  • , Rabab S. Jassas
  • , Hatem M. Altass
  • , Moataz Morad
  • , Ziad Moussa
  • , Saleh A. Ahmed

Research output: Contribution to journalArticlepeer-review

Abstract

β-Hydroxynitriles are essential intermediates in the synthesis of diverse bioactive compounds and clinical drugs. One of the precursor reactions to these intermediates is the opening of an epoxide ring with a cyanide nucleophile. In the present study, we report a milder and safer route to β-hydroxynitriles employing recyclable, Amberlyst A-21 resin in the ring-opening of epoxides with acetone cyanohydrin in water. A diverse range of substrates (fifteen), including aromatic epoxides, phenoxy epoxides, non-terminal, and terminal aliphatic epoxides, are investigated under the optimized conditions to afford the desired β-hydroxynitriles in good to excellent yield. In addition to this, the recyclability of the Amberlyst A-21 resin is also successfully demonstrated. This relatively safer methodology has the potential to be explored in other organic transformations.

Original languageEnglish
Pages (from-to)8200-8208
Number of pages9
JournalArabian Journal of Chemistry
Volume13
Issue number11
DOIs
Publication statusPublished - Nov 2020

Keywords

  • Acetone cyanohydrin
  • Amberlyst A-21
  • Epoxide opening
  • Water
  • β-Hydroxynitriles

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering

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