Vinylbenziodoxol(on)es: Synthetic Methods and Applications |
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| Authors: | Nina Declas Guillaume Pisella Jerome Waser |
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| Institution: | 1. Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, Av. Forel 2, CH-1015 Lausanne, Switzerland
These authors contributed equally.;2. Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, Av. Forel 2, CH-1015 Lausanne, Switzerland |
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| Abstract: | Cyclic hypervalent iodine reagents are now frequently used in synthetic organic chemistry, either as oxidants or group-transfer reagents. Vinylbenziodoxol(on)es (VBXs) bearing alkene substituents have been less investigated than the corresponding trifluoromethyl or alkynyl reagents. Nevertheless, since 2016 the development of new synthetic methods to access VBXs has awakened the interest of the synthetic community, leading to new transformations highlighting their unique reactivity as electrophilic alkene synthons. In this review, an overview of the synthesis and applications of VBX reagents will be presented. The review is organized according to the two main classes of VBX reagents reported so far – simple alkyl/aryl-substituted VBXs and heteroatom (S, O, N, X)-substituted VBXs – as they differ significantly from the point of view of synthetic access. |
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| Keywords: | alkenes benziodoxolones hypervalent compounds iodine umpolung vinylation |
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