title: Reaction of alkenes with hydrogen peroxide and sodium iodide: a nonenzymatic biogenic-like approach to iodohydrins.
abstract: An efficient protocol to synthesize iodohydrins from alkenes is presented. Reactions were conducted in aqueous media using safe and readily available sodium iodide (the most abundant form of the element), and a highly convenient oxidant such as hydrogen peroxide. Addition of a protic acid triggers a faster and efficient process, a role formally related to that played by haloperoxidase enzymes in naturally occurring transformations. The successful application of these conditions to multigram scale preparations and over natural products derivatives is also discussed.
authors.affiliation: Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al C.S.I.C., Universidad de Oviedo, C/Julián Clavería, 8, 33006 Oviedo, Spain. barluenga@uniovi.es
authors.forename: José
authors.initials: J
authors.lastname: Barluenga
authors.forename: María
authors.initials: M
authors.lastname: Marco-Arias
authors.forename: Francisco
authors.initials: F
authors.lastname: González-Bobes
authors.forename: Alfredo
authors.initials: A
authors.lastname: Ballesteros
authors.forename: José M
authors.initials: JM
authors.lastname: González
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D032701:Biomimetics / Q000379:methods; D003511:Cyclohexanols / Q000138:chemical synthesis / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry; D008968:Molecular Conformation; D012974:Sodium Iodide / Q000737:chemistry*
chemical_list: D000475:Alkenes; D003511:Cyclohexanols; D007455:Iodine; D006861:Hydrogen Peroxide; D012974:Sodium Iodide