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Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N‐Fluorinated Sulfonimides with Simple Alkynes
The facile synthesis of aminoallenes, accomplished by a selenium‐π‐acid‐catalyzed cross‐coupling of an N‐fluorinated sulfonimide with simple, non‐activated alkynes, is reported. Until now, aminoallenes were difficult to be accessed by customary means, inasmuch as pre‐activated and, in part, intricat...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7986078/ https://www.ncbi.nlm.nih.gov/pubmed/33776555 http://dx.doi.org/10.1002/ejoc.202001673 |
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author | Rode, Katharina Ramadas Narasimhamurthy, Poorva Rieger, Rene Krätzschmar, Felix Breder, Alexander |
author_facet | Rode, Katharina Ramadas Narasimhamurthy, Poorva Rieger, Rene Krätzschmar, Felix Breder, Alexander |
author_sort | Rode, Katharina |
collection | PubMed |
description | The facile synthesis of aminoallenes, accomplished by a selenium‐π‐acid‐catalyzed cross‐coupling of an N‐fluorinated sulfonimide with simple, non‐activated alkynes, is reported. Until now, aminoallenes were difficult to be accessed by customary means, inasmuch as pre‐activated and, in part, intricate starting materials were necessary for their synthesis. In sharp contrast, the current study shows that ordinary internal alkynes can serve as simple and readily available precursors for the construction of the aminoallene motif. The operating reaction conditions tolerate numerous functional groups such as esters, nitriles, (silyl)ethers, acetals, and halogen substituents, furnishing the target compounds in up to 86 % yield. |
format | Online Article Text |
id | pubmed-7986078 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-79860782021-03-25 Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N‐Fluorinated Sulfonimides with Simple Alkynes Rode, Katharina Ramadas Narasimhamurthy, Poorva Rieger, Rene Krätzschmar, Felix Breder, Alexander European J Org Chem Communications The facile synthesis of aminoallenes, accomplished by a selenium‐π‐acid‐catalyzed cross‐coupling of an N‐fluorinated sulfonimide with simple, non‐activated alkynes, is reported. Until now, aminoallenes were difficult to be accessed by customary means, inasmuch as pre‐activated and, in part, intricate starting materials were necessary for their synthesis. In sharp contrast, the current study shows that ordinary internal alkynes can serve as simple and readily available precursors for the construction of the aminoallene motif. The operating reaction conditions tolerate numerous functional groups such as esters, nitriles, (silyl)ethers, acetals, and halogen substituents, furnishing the target compounds in up to 86 % yield. John Wiley and Sons Inc. 2021-03-08 2021-03-19 /pmc/articles/PMC7986078/ /pubmed/33776555 http://dx.doi.org/10.1002/ejoc.202001673 Text en © 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Communications Rode, Katharina Ramadas Narasimhamurthy, Poorva Rieger, Rene Krätzschmar, Felix Breder, Alexander Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N‐Fluorinated Sulfonimides with Simple Alkynes |
title | Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N‐Fluorinated Sulfonimides with Simple Alkynes |
title_full | Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N‐Fluorinated Sulfonimides with Simple Alkynes |
title_fullStr | Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N‐Fluorinated Sulfonimides with Simple Alkynes |
title_full_unstemmed | Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N‐Fluorinated Sulfonimides with Simple Alkynes |
title_short | Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N‐Fluorinated Sulfonimides with Simple Alkynes |
title_sort | synthesis of aminoallenes via selenium‐π‐acid‐catalyzed cross‐coupling of n‐fluorinated sulfonimides with simple alkynes |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7986078/ https://www.ncbi.nlm.nih.gov/pubmed/33776555 http://dx.doi.org/10.1002/ejoc.202001673 |
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