Issue 31, 2016

Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(i) reagents under metal-free conditions

Abstract

Metal-free, molecular iodine-free direct 1,2-difunctionalization of unactivated alkenes has been reported. The sulfonium iodate(I) reagent efficiently promoted the intermolecular vicinal iodo-functionalization of a diverse range of olefins in a stereo and regioselective manner. This method enables the divergent and straightforward preparation of synthetically useful functionalities; β-iodocarboxylates, β-iodohydrins, and β-iodoethers in a one-step process. Further interconversion of iodo-functionalized derivatives allows easy access to valuable synthetic intermediates en route to biologically active molecules.

Graphical abstract: Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(i) reagents under metal-free conditions

Supplementary files

Article information

Article type
Paper
Submitted
31 May 2016
Accepted
01 Jul 2016
First published
04 Jul 2016

Org. Biomol. Chem., 2016,14, 7529-7543

Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(I) reagents under metal-free conditions

D. S. Rao, T. R. Reddy, K. Babachary and S. Kashyap, Org. Biomol. Chem., 2016, 14, 7529 DOI: 10.1039/C6OB01179A

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