An environmentally friendly preparation of iodohydrins from alkenes mediated by clay-minerals

Versatile and Iodine Atom-Economic Co-Iodination of Alkenes

“…Activation of elemental iodine for addition to alkenes, by modifying its electrophilicity, has been achieved using transition-metal salts or oxidizing agents . Other electrophilic iodinating agents commonly employed for iodination of organic molecules include N -iodosuccinimide and other N−I compounds, bis(pyridinium)iodonium(I) tetrafluoroborate, I 2 -clays, and in situ generated acyl hypoidoite using a combination of elemental iodine and hypervalent iodine reagents, to name a few. Though these iodinating agents are excellent sources of I + and provide good to excellent yields of iodinated products, the use of these reagents produces considerable waste and has no more than 50% iodine atom economy in the reaction.…”

Fe2(SO4)3-mediated Coiodination of Alkenes with Acetic Acid: A Convenient and Regioselective Eco-friendly Preparation of β-iodoacetates

“…17 In previous work, 18 we reported an easy and efficient synthesis of iodohydrins from the coiodination of alkenes with water mediated by diverse metal salts, one of the most effective being the ready available, less toxic and inexpensive Fe 2 (SO 4 ) 3 . Continuing our interest in cohalogenation of alkenes with oxygenated nucleophiles, 19 we present here our results on the coiodination with acetic acid mediated by Fe 2 (SO 4 ) 3 .…”

Green Alkoxyiodination of Cyclohexene Mediated by Natural Clay

“…[1 -3] b-Iodoethers are useful intermediates in synthetic organic chemistry [4,5] and are used in radiodiagnosis. [8] Continuing our interest in the cohalogenation of alkenes, [9 -12] we communicate here the results of the reaction of cyclohexene with I 2 /alcohols in the presence of clays and compare the results with traditional metal salt-mediated reactions. [7] Recently we published the hydroxyiodination (coiodination with water) of several alkenes mediated by clay minerals as an efficient route for the preparation of iodohydrins.…”