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Atherton–Todd reaction: mechanism, scope and applications
Initially, the Atherton–Todd (AT) reaction was applied for the synthesis of phosphoramidates by reacting dialkyl phosphite with a primary amine in the presence of carbon tetrachloride. These reaction conditions were subsequently modified with the aim to optimize them and the reaction was extended to...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077366/ https://www.ncbi.nlm.nih.gov/pubmed/24991268 http://dx.doi.org/10.3762/bjoc.10.117 |
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author | Le Corre, Stéphanie S Berchel, Mathieu Couthon-Gourvès, Hélène Haelters, Jean-Pierre Jaffrès, Paul-Alain |
author_facet | Le Corre, Stéphanie S Berchel, Mathieu Couthon-Gourvès, Hélène Haelters, Jean-Pierre Jaffrès, Paul-Alain |
author_sort | Le Corre, Stéphanie S |
collection | PubMed |
description | Initially, the Atherton–Todd (AT) reaction was applied for the synthesis of phosphoramidates by reacting dialkyl phosphite with a primary amine in the presence of carbon tetrachloride. These reaction conditions were subsequently modified with the aim to optimize them and the reaction was extended to different nucleophiles. The mechanism of this reaction led to controversial reports over the past years and is adequately discussed. We also present the scope of the AT reaction. Finally, we investigate the AT reaction by means of exemplary applications, which mainly concern three topics. First, we discuss the activation of a phenol group as a phosphate which allows for subsequent transformations such as cross coupling and reduction. Next, we examine the AT reaction applied to produce fire retardant compounds. In the last section, we investigate the use of the AT reaction for the production of compounds employed for biological applications. The selected examples to illustrate the applications of the Atherton–Todd reaction mainly cover the past 15 years. |
format | Online Article Text |
id | pubmed-4077366 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-40773662014-07-02 Atherton–Todd reaction: mechanism, scope and applications Le Corre, Stéphanie S Berchel, Mathieu Couthon-Gourvès, Hélène Haelters, Jean-Pierre Jaffrès, Paul-Alain Beilstein J Org Chem Review Initially, the Atherton–Todd (AT) reaction was applied for the synthesis of phosphoramidates by reacting dialkyl phosphite with a primary amine in the presence of carbon tetrachloride. These reaction conditions were subsequently modified with the aim to optimize them and the reaction was extended to different nucleophiles. The mechanism of this reaction led to controversial reports over the past years and is adequately discussed. We also present the scope of the AT reaction. Finally, we investigate the AT reaction by means of exemplary applications, which mainly concern three topics. First, we discuss the activation of a phenol group as a phosphate which allows for subsequent transformations such as cross coupling and reduction. Next, we examine the AT reaction applied to produce fire retardant compounds. In the last section, we investigate the use of the AT reaction for the production of compounds employed for biological applications. The selected examples to illustrate the applications of the Atherton–Todd reaction mainly cover the past 15 years. Beilstein-Institut 2014-05-21 /pmc/articles/PMC4077366/ /pubmed/24991268 http://dx.doi.org/10.3762/bjoc.10.117 Text en Copyright © 2014, Le Corre et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Review Le Corre, Stéphanie S Berchel, Mathieu Couthon-Gourvès, Hélène Haelters, Jean-Pierre Jaffrès, Paul-Alain Atherton–Todd reaction: mechanism, scope and applications |
title | Atherton–Todd reaction: mechanism, scope and applications |
title_full | Atherton–Todd reaction: mechanism, scope and applications |
title_fullStr | Atherton–Todd reaction: mechanism, scope and applications |
title_full_unstemmed | Atherton–Todd reaction: mechanism, scope and applications |
title_short | Atherton–Todd reaction: mechanism, scope and applications |
title_sort | atherton–todd reaction: mechanism, scope and applications |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077366/ https://www.ncbi.nlm.nih.gov/pubmed/24991268 http://dx.doi.org/10.3762/bjoc.10.117 |
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