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N‐Heterocycle‐Stabilized Iodanes: From Structure to Reactivity
Author(s) -
Boelke Andreas,
Lork Enno,
Nachtsheim Boris J.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804957
Subject(s) - hypervalent molecule , reactivity (psychology) , chemistry , reagent , amide , aryl , organic chemistry , heteroatom , derivatization , combinatorial chemistry , alkyl , high performance liquid chromatography , medicine , alternative medicine , pathology
Pseudocyclic aryl‐λ 3 ‐iodanes are superior reagents for a variety of oxidative transformations due to a well‐balanced relation between stability, solubility and reactivity. Their properties are substantially influenced by a dative interaction between a Lewis base, in general the oxygen atom of a carboxylic acid or an amide, and the central hypervalent iodine atom. This work presents the first systematic investigation of pseudocyclic N‐heterocycle‐stabilized iodanes (NHIs). The synthesis of these throughout shelf‐stable solids is robust and can be achieved on a large scale. Their reactivity is highly tunable, depending on the stabilizing heterocycle. Solid state structures of selected derivatives are reported and their reactivity in a model oxygen transfer reaction is compared. Further derivatization reactions to N‐heterocycle‐stabilized pseudocyclic diaryliodonium salts and cyclic iodoso species are presented as well.