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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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| Item type | Article | ||||
| Journal or Publication Title | European 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 | ||||
| Date | 8 March 2021 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie | ||||
| Identification Number |
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| Keywords | PROTOTROPIC ISOMERIZATIONS; ALLENES; π -Acids; Amination; Homogeneous catalysis; Oxidations; Selenium | ||||
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Partially | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-451859 | ||||
| Item ID | 45185 |
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