Iodohydrins and corresponding ethers were synthesized by an electrochemical process using inexpensive and non-toxic ammonium iodide. This transformation was applied to a panel of alkenes, giving products without the need of external hazardous oxidants, reductants or metal catalyst. This protocol showed a general efficiency to synthesize valuable iodinated molecules with yields from 19% to 90%.
m-Iodosylbenzoic acid, a tagged hypervalent iodine reagent for the iodo-functionalization of alkenes and alkynes
作者:Mekhman S. Yusubov、Roza Ya. Yusubova、Andreas Kirschning、Joo Yeon Park、Ki-Whan Chi
DOI:10.1016/j.tetlet.2007.12.120
日期:2008.2
An efficient and facile method for the iodo-functionalization of alkenes 5 and alkynes 6 by using recyclable ni-iodosylbenzoic acid (2) was developed. The final products can be easily isolated without any chromatographic purification by simple treatment of the crude mixture with an anionic exchange resin. Unreacted m-iodosylbenzoic acid and reduced m-iodobenzoic acid are effectively recovered from the resin by acidification with hydrochloric acid. (c) 2008 Elsevier Ltd. All rights reserved.
Iodomethane Oxidation by Dimethyldioxirane: A New Route to Hypoiodous Acid and Iodohydrines
作者:Gregorio Asensio、Cecilia Andreu、Carmen Boix-Bernardini、Rossella Mello、María Elena González-Nuñez
DOI:10.1021/ol9903281
日期:1999.12.1
[GRAPHICS]The oxidation of iodomethane with dimethyldioxirane allows the generation of stable neutral solutions of hypoiodous acid in the absence of any trapping agent for iodide anion. Hypoiodous acid is trapped in situ by addition to representative olefins to give iodohydrines in good yields. The stereochemical study of the products shows the anti-stereospecific nature of the iodohydroxylation reaction.