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A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7003988/ https://www.ncbi.nlm.nih.gov/pubmed/31600009 http://dx.doi.org/10.1002/anie.201912023 |
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author | Abazid, Ayham H. Nachtsheim, Boris J. |
author_facet | Abazid, Ayham H. Nachtsheim, Boris J. |
author_sort | Abazid, Ayham H. |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-7003988 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-70039882020-02-11 A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations Abazid, Ayham H. Nachtsheim, Boris J. Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2019-12-12 2020-01-20 /pmc/articles/PMC7003988/ /pubmed/31600009 http://dx.doi.org/10.1002/anie.201912023 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Abazid, Ayham H. Nachtsheim, Boris J. A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations |
title | A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
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title_full | A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
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title_fullStr | A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
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title_full_unstemmed | A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
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title_short | A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
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title_sort | triazole‐substituted aryl iodide with omnipotent reactivity in enantioselective oxidations |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7003988/ https://www.ncbi.nlm.nih.gov/pubmed/31600009 http://dx.doi.org/10.1002/anie.201912023 |
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