A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
| Autor: | Ayham H. Abazid, Boris J. Nachtsheim |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
inorganic chemicals
oxidation Iodide Substituent Triazole asymmetric oxidation 010402 general chemistry 01 natural sciences Catalysis chemistry.chemical_compound Reactivity (chemistry) heterocyclic compounds stereoselective synthesis chemistry.chemical_classification 010405 organic chemistry Organocatalysis Aryl organic chemicals Communication Enantioselective synthesis General Chemistry General Medicine Combinatorial chemistry Communications 0104 chemical sciences chiral hypervalent iodine compounds chemistry Selectivity |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3757 0044-8249 |
| DOI: | 10.1002/ange.201912023 |
| Popis: | A widely applicable triazole‐substituted chiral aryl iodide is described as catalyst for enantioselective oxidation reactions. The introduction of a substituent in ortho‐position to the iodide is key for its high reactivity and selectivity. Besides a robust and modular synthesis, the main advantage of this catalyst is the excellent performance in a plethora of mechanistically diverse enantioselective transformations, such as spirocyclizations, phenol dearomatizations, α‐oxygenations, and oxidative rearrangements. DFT‐calculations of in situ generated [hydroxy(tosyloxy)iodo]arene isomers give an initial rational for the observed reactivity. A good all‐rounder: An easy to synthesize chiral triazole‐substituted aryl iodide is described as an omnipotent catalyst for a variety of iodane‐mediated enantioselective oxidations. It outperforms all existing chiral hypervalent iodine precursors. |
| Databáze: | OpenAIRE |
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