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

2 Citations (Scopus)

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

  • Chemistry(all)
  • Chemical Engineering(all)

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