Facile synthesis of vicinal halohydrins via organocatalytic halogen nucleophile-induced regioselective opening of epoxides
Keyword(s):
Background: The calix[4]pyrrole is reported as a novel organocatalyst for regioselective ring opening of epoxides under mild reaction conditions. Methods: The reaction involves elemental halogen as a nucleophile to afford vicinal halohydrins in good to excellent yield (75-95%). Results : The reactivity of the halide anion 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. Conclusion: An efficient methodology has been developed for the regioselective synthesis of halohydrins in good to excellent yields.
2008 ◽
Vol 12
(09)
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pp. 1030-1040
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2006 ◽
Vol 34
(2)
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pp. 291-295
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2018 ◽
Vol 20
(27)
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pp. 18241-18251
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2019 ◽
2011 ◽
Vol 41
(12)
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pp. 1829-1837
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Keyword(s):
2016 ◽
Vol 72
(12)
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pp. 1762-1767