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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...

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Detalles Bibliográficos
Autores principales: Abazid, Ayham H., Nachtsheim, Boris J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
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.
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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
title_full A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
title_fullStr A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
title_full_unstemmed A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
title_short A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
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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