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. 2016 Nov 2;22(45):16066-16070.
doi: 10.1002/chem.201603955. Epub 2016 Oct 6.

Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents

Elin Stridfeldt  1 , Alexandra Seemann  1 , Marinus J Bouma  1 , Chandan Dey  1 , Anne Ertan  2 , Berit Olofsson  3
Affiliations

Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents

Elin Stridfeldt et al. Chemistry. .

Abstract

A novel type of hypervalent iodine(III) reagents, vinylbenziodoxolones (VBX), has been synthesized in a one-pot reaction from 2-iodobenzoic acid. VBX is bench stable, has been thoroughly characterized and the cyclic structure is supported by X-ray analysis. The reactivity of VBX was investigated in vinylation of nitrocyclohexane, and delivered vinylated products with opposite regioselectivity compared to acyclic vinyl(aryl)iodonium salts. The reagents could become a powerful tool in vinylation reactions under both metal-free and metal-catalyzed conditions.

Keywords: benziodoxolones; hypervalent compounds; structure analysis; synthetic methods; vinylation.

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