Synthesis, structural characterization, reactivity and catalytic activity of mixed halo/triflate ArI(OTf)(X) species

Both mixed λ 3 -iodoarenes and λ 3 -iodoarenes possessing -OTf ligands are coveted for their enhanced reactivities. Here we describe the synthesis, reactivity, and comprehensive characterisation of two new ArI(OTf)(X) species, a class of compound that were previously only invoked as reactive interme...

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Bibliographic Details
Published inDalton transactions : an international journal of inorganic chemistry Vol. 52; no. 11; pp. 3358 - 337
Main Authors Sharp-Bucknall, Lachlan, Sceney, Marcus, White, Keith F, Dutton, Jason L
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 14.03.2023
Subjects
Aromatic compounds
Catalytic activity
Chemical synthesis
Chlorine
Reactivity
Structural analysis
Substrates
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Summary:Both mixed λ 3 -iodoarenes and λ 3 -iodoarenes possessing -OTf ligands are coveted for their enhanced reactivities. Here we describe the synthesis, reactivity, and comprehensive characterisation of two new ArI(OTf)(X) species, a class of compound that were previously only invoked as reactive intermediates where X = Cl, F and their divergent reactivity with aryl substrates. A new catalytic system for electrophilic chlorination of deactivated arenes using Cl 2 as the chlorine source and ArI/HOTf as the catalyst is also described. Targeted isolation of two previously inaccessible I( iii ) halotriflates. The chloride analoge is a powerful electrophilic chlorinating reagent that can be generated in a catalytic manner to enhance Cl 2 reactivity.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
https://doi.org/10.1039/d3dt00275f
2219970
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-9226
1477-9234
DOI:10.1039/d3dt00275f