Preparation and chemistry of phosphoranyl-derived iodanes

Viktor Zhdankin, Olena Maydanovych, Jon Herschbach, Jessica Bruno, Elena D. Matveeva, Nikolai S. Zefirov

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

The preparation and chemistry of novel phosphoranyl-derived λ3-iodanes is reported. The phosphoranyl-derived phenyliodonium sulfonates were prepared in good yields by the reaction of stabilized phosphonium ylides [1-triphenylphosphoranylidene-2-propanone, methyl(triphenylphosphoranylidene)acetate, (triphenylphosphoranylidene)acetaldehyde, and (triphenylphosphoranylidene)acetonitrile] with the pyridinium complex of iodobenzene ditriflate or with [hydroxy(tosyloxy)-iodo]benzene under mild conditions. These compounds represent a potentially useful class of reagents that combine in one molecule synthetic advantages of a phosphonium ylide and an iodonium salt. Specifically, phosphorane-derived phenyliodonium tosylates can react with soft nucleophiles, such as iodide, bromide, benzenesulfinate, and thiophenolate anions, with a selective formation of the respective α-functionalized phosphonium ylides, which can be further converted to alkenes by the Wittig reaction with benzaldehyde. The phosphoranyl-derived benziodoxoles can be prepared by the reaction of 1-acetoxybenziodoxole with stabilized phosphonium ylides. An unusual ligand exchange on the iodine(III) center resulting in the substitution of a carbon ligand with an oxygen ligand was observed in the reaction of these compounds with strong acids.

Original languageEnglish (US)
Pages (from-to)1018-1023
Number of pages6
JournalJournal of Organic Chemistry
Volume68
Issue number3
DOIs
StatePublished - Feb 7 2003

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    Zhdankin, V., Maydanovych, O., Herschbach, J., Bruno, J., Matveeva, E. D., & Zefirov, N. S. (2003). Preparation and chemistry of phosphoranyl-derived iodanes. Journal of Organic Chemistry, 68(3), 1018-1023. https://doi.org/10.1021/jo026604y