An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α‐cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characteriza...

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Detalles Bibliográficos
Autores principales: Bauer, Adriano, Di Mauro, Giovanni, Li, Jing, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7589340/
https://www.ncbi.nlm.nih.gov/pubmed/32808419
http://dx.doi.org/10.1002/anie.202007439
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author Bauer, Adriano
Di Mauro, Giovanni
Li, Jing
Maulide, Nuno
author_facet Bauer, Adriano
Di Mauro, Giovanni
Li, Jing
Maulide, Nuno
author_sort Bauer, Adriano
collection PubMed
description The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α‐cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non‐classical carbocations.
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spelling pubmed-75893402020-10-30 An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung Bauer, Adriano Di Mauro, Giovanni Li, Jing Maulide, Nuno Angew Chem Int Ed Engl Communications The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α‐cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non‐classical carbocations. John Wiley and Sons Inc. 2020-08-17 2020-10-05 /pmc/articles/PMC7589340/ /pubmed/32808419 http://dx.doi.org/10.1002/anie.202007439 Text en © 2020 The Authors. Published by Wiley-VCH GmbH 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
Bauer, Adriano
Di Mauro, Giovanni
Li, Jing
Maulide, Nuno
An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
title An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
title_full An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
title_fullStr An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
title_full_unstemmed An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
title_short An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
title_sort α‐cyclopropanation of carbonyl derivatives by oxidative umpolung
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7589340/
https://www.ncbi.nlm.nih.gov/pubmed/32808419
http://dx.doi.org/10.1002/anie.202007439
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