Electrophilic monoiodination of terminal alkenes

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

doi:10.1039/C3OB27348B

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Organic & Biomolecular Chemistry

Issue 17, 2013

The international home of synthetic, physical and biomolecular organic chemistry.

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Paper

Electrophilic monoiodination of terminal alkenes

Sergiy V. Yemets,^a Tatyana E. Shubina^b and Pavel A. Krasutsky*^a

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Corresponding authors

University of Minnesota, Natural Resources Research Institute, 5013 Miller Trunk Highway, Duluth, USA
E-mail: pkrasuts@nrri.umn.edu

Computer-Chemie-Centrum and Interdisciplinary Center for Molecular Materials, University Erlangen-Nuremberg, Nägelsbachstr 25, Germany 91052

Org. Biomol. Chem., 2013,11, 2891-2897

DOI: 10.1039/C3OB27348B
Received 03 Dec 2012, Accepted 20 Feb 2013
First published online 21 Feb 2013

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Abstract
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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.