H2TPP organocatalysis in mild and highly regioselective ring opening of epoxides to halo alcohols by means of halogen elements.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Parviz TorabiShahab Zomorodbakhsh

Abstract

We found that elemental iodine and bromine are converted to trihalide nucleophiles (triiodine and tribromide anion, respectively) in the presence of catalytic amounts of meso-tetraphenylporphyrins (H2TPP). Therefore a highly regioselective method for the synthesis of beta-haloalcohols through direct ring opening of epoxides with elemental iodine and bromine in the presence of H2TPPs as new catalysts is described. At room temperature a series of epoxide derivatives were converted into the corresponding halohydrins resulting from an attack of trihalide species anion atoms at the less substituted carbon atom. This method occurs under neutral and mild conditions with high yields in various aprotic solvents, even when sensitive functional groups are present.

References

Jan 5, 1999·Bioorganic & Medicinal Chemistry Letters·G I GeorgR H Himes
Sep 6, 2002·Bioorganic & Medicinal Chemistry·Tsutomu AgatsumaYutaka Saitoh
Apr 15, 2002·Angewandte Chemie·Joseph M Ready, Eric N Jacobsen
Aug 1, 1988·Journal of the American Chemical Society·N N JoshiH C Brown

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Citations

Jun 1, 2017·Anais Da Academia Brasileira De Ciências·Derisvaldo R PaivaAdilson Beatriz

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Methods Mentioned

BETA
column chromatography

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