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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

Rode, Katharina, Ramadas Narasimhamurthy, Poorva, Rieger, Rene, Krätzschmar, Felix and Breder, Alexander (2021) Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N ‐Fluorinated Sulfonimides with Simple Alkynes. European Journal of Organic Chemistry 2021 (11), pp. 1720-1725.

Date of publication of this fulltext: 11 Mar 2021 11:31
Article
DOI to cite this document: 10.5283/epub.45185


Abstract

The facile synthesis of aminoallenes, accomplished by a selenium-pi-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 ...

The facile synthesis of aminoallenes, accomplished by a selenium-pi-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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Details

Item typeArticle
Journal or Publication TitleEuropean Journal of Organic Chemistry
Publisher:Wiley
Open Access Type:DEAL (Wiley)
Place of Publication:WEINHEIM
Volume:2021
Number of Issue or Book Chapter:11
Page Range:pp. 1720-1725
Date8 March 2021
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie
Identification Number
ValueType
10.1002/ejoc.202001673DOI
KeywordsPROTOTROPIC ISOMERIZATIONS; ALLENES; π -Acids; Amination; Homogeneous catalysis; Oxidations; Selenium
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgPartially
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-451859
Item ID45185

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