Issue 17, 2013
From the journal:

Organic & Biomolecular Chemistry

Electrophilic monoiodination of terminal alkenes†

Sergiy V. Yemets,a   Tatyana E. Shubinab  and  Pavel A. Krasutsky*a  

* Corresponding authors

a University of Minnesota, Natural Resources Research Institute, 5013 Miller Trunk Highway, Duluth, MN 55811, USA
E-mail: pkrasuts@nrri.umn.edu

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

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.

Graphical abstract: Electrophilic monoiodination of terminal alkenes

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Article information

DOI
https://doi.org/10.1039/C3OB27348B
Article type
Paper
Submitted
03 Dec 2012
Accepted
20 Feb 2013
First published
21 Feb 2013

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

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Electrophilic monoiodination of terminal alkenes

S. V. Yemets, T. E. Shubina and P. A. Krasutsky, Org. Biomol. Chem., 2013, 11, 2891 DOI: 10.1039/C3OB27348B

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