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Vinylbenziodoxol(on)es: Synthetic Methods and Applications
Author(s) -
Declas Nina,
Pisella Guillaume,
Waser Jerome
Publication year - 2020
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202000191
Subject(s) - chemistry , synthon , alkene , reagent , hypervalent molecule , electrophile , organic synthesis , combinatorial chemistry , aryl , organic chemistry , trifluoromethyl , alkyl , catalysis
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.