Reaction of alkenes with hydrogen peroxide and sodium iodide: a nonenzymatic biogenic-like approach to iodohydrins.
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.
Barluenga
José
J
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
Marco-Arias
María
M
González-Bobes
Francisco
F
Ballesteros
Alfredo
A
González
José M
JM
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*
D000475:Alkenes; D003511:Cyclohexanols; D007455:Iodine; D006861:Hydrogen Peroxide; D012974:Sodium Iodide