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

Autor: 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
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: Arabian Journal of Chemistry, Vol 13, Iss 11, Pp 8200-8208 (2020)
Druh dokumentu: article
ISSN: 1878-5352
DOI: 10.1016/j.arabjc.2020.09.053
Popis: 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.
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