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Molecules 2012, 17(5), 5508-5519; doi:10.3390/molecules17055508
Article

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

1,* , 2 and 1
Received: 10 January 2012; in revised form: 6 April 2012 / Accepted: 12 April 2012 / Published: 9 May 2012
(This article belongs to the Special Issue Organocatalysis)
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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.
Keywords: oxirane; ring opening; nucleophilic addition; elemental halogen; meso-tetraarylporphyrine; halohydrine oxirane; ring opening; nucleophilic addition; elemental halogen; meso-tetraarylporphyrine; halohydrine
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA 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(5):5508-5519.

Chicago/Turabian Style

Torabi, Parviz; Azizian, Javad; Zomorodbakhsh, Shahab. 2012. "H2TPP Organocatalysis in Mild and Highly Regioselective Ring Opening of Epoxides to Halo Alcohols by Means of Halogen Elements." Molecules 17, no. 5: 5508-5519.


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