Next Article in Journal
Saponins with Neuroprotective Effects from the Roots of Pulsatilla cernua
Next Article in Special Issue
Asymmetric Synthesis of the Carbon-14-Labeled Selective Glucocorticoid Receptor Modulator using Cinchona Alkaloid Catalyzed Addition of 6-Bromoindole to Ethyl Trifluoropyruvate
Previous Article in Journal
Quinoline-3-carboxamide Derivatives as Potential Cholesteryl Ester Transfer Protein Inhibitors
Previous Article in Special Issue
Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans
Article Menu

Export Article

Open AccessArticle
Molecules 2012, 17(5), 5508-5519; https://doi.org/10.3390/molecules17055508

H2TPP Organocatalysis in Mild and Highly Regioselective Ring Opening of Epoxides to Halo Alcohols by Means of Halogen Elements

1
Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr 63519, Iran
2
Department of Chemistry, Faculty of Science, Science and Research Branch, Islamic Azad University, Tehran 11365, Iran
*
Author to whom correspondence should be addressed.
Received: 10 January 2012 / Revised: 6 April 2012 / Accepted: 12 April 2012 / Published: 9 May 2012
(This article belongs to the Special Issue Organocatalysis)
Full-Text   |   PDF [375 KB, uploaded 18 June 2014]   |  

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 b-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. View Full-Text
Keywords: oxirane; ring opening; nucleophilic addition; elemental halogen; meso-tetraarylporphyrine; halohydrine oxirane; ring opening; nucleophilic addition; elemental halogen; meso-tetraarylporphyrine; halohydrine
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

MDPI and ACS Style

Torabi, P.; Azizian, J.; Zomorodbakhsh, S. H2TPP Organocatalysis in Mild and Highly Regioselective Ring Opening of Epoxides to Halo Alcohols by Means of Halogen Elements. Molecules 2012, 17, 5508-5519.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top