Electrophilic monoiodination of terminal alkenes

Sergiy V Yemets, Tatyana E. Shubina, Pavel A. Krasutsky

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

An excess of elemental iodine in N,N-dimethylacetamide enables effective 3/iodanylium-de-hydronation of terminal alkenes with 3-iodopropene derivatives and hydrogen iodide formation within minutes at room temperature. The optimal molar ratio of iodine to substrate was decreased to 1:1 when hydrogen iodide formed was oxidized on a platinum anode. The electrolytic oxidation recovers iodine as a reagent and diminishes the hydrogen iodide inhibitory action to accomplish the monoiodination. The proposed reaction mechanism is based on kinetic measurements and quantum mechanics calculations.

Original languageEnglish (US)
Pages (from-to)2891-2897
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number17
DOIs
StatePublished - May 7 2013

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