title: H2TPP organocatalysis in mild and highly regioselective ring opening of epoxides to halo alcohols by means of halogen elements.
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.
authors.affiliation: Department of Chemistry, Islamic Azad University, Mahshahr Branch, Mahshahr 63519, Iran. p.torabi@mahshahriau.ac.ir
authors.forename: Parviz
authors.initials: P
authors.lastname: Torabi
authors.forename: Javad
authors.initials: J
authors.lastname: Azizian
authors.forename: Shahab
authors.initials: S
authors.lastname: Zomorodbakhsh
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis*; D000838:Anions; D001966:Bromine / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D011166:Porphyrins / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013696:Temperature
chemical_list: C509964:5,10,15,20-tetraphenylporphyrin; D000438:Alcohols; D000838:Anions; D004852:Epoxy Compounds; D011166:Porphyrins; D002244:Carbon; D007455:Iodine; D001966:Bromine