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

Molecules

Parviz Torabi¹  Javad Azizian¹ 

[1] ¹Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr 63519, Iran ²Department of Chemistry, Faculty of Science, Science and Research Branch, Islamic Azad University, Tehran 11365, Iran

关键词: oxirane;    ring opening;    nucleophilic addition;    elemental halogen;    meso-tetraarylporphyrine;    halohydrine;   

DOI  :  10.3390/molecules17055508

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.