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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...

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Autores principales: Rode, Katharina, Ramadas Narasimhamurthy, Poorva, Rieger, Rene, Krätzschmar, Felix, Breder, Alexander
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
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.
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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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