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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Facile Synthesis of Vicinal Halohydrins Via Organocatalytic Halogen Nucleophile-Induced Regioselective Opening of Epoxides

Author(s): Niharika Sinha*, Anchal Singhal, Deeksha Sharma and Shiv Murat Singh Chauhan*

Volume 19, Issue 6, 2022

Published on: 12 January, 2022

Page: [490 - 497] Pages: 8

DOI: 10.2174/1570178618666211001114243

Price: $65

Abstract

The calix[4]pyrrole is reported as a novel organocatalyst for regioselective ringopening of epoxides under mild reaction conditions. The reaction involves elemental halogen as a nucleophile to afford vicinal halohydrins in good to excellent yield (75-95%). The reactivity of the halide ion in the reaction is governed by different factors, including solvent polarity, temperature and non-covalent interactions of the functional group present on calix[4]pyrrole moiety with halide ions. An efficient methodology has been developed for the regioselective synthesis of halohydrins in good to excellent yields.

Keywords: Calixpyrrole, epoxides, halohydrins, elemental halogen, organocatalysis, regioselective.

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