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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

Artikel

Rode, Katharina, Ramadas Narasimhamurthy, Poorva, Rieger, Rene, Krätzschmar, Felix und 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), S. 1720-1725.

DOI zum Zitieren dieses Dokuments: 10.5283/epub.45185


Zusammenfassung

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

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftEuropean Journal of Organic Chemistry
VerlagWiley
Open Access ArtDEAL (Wiley)
Ort der VeröffentlichungWEINHEIM
Band2021
Nummer des Zeitschriftenheftes oder des Kapitels11
SeitenbereichS. 1720-1725
Datum8 März 2021
Veröffentlichungsdatum11 Mrz 2021 11:31
InstitutionenChemie und Pharmazie > Institut für Organische Chemie
Identifikationsnummer
WertTyp
10.1002/ejoc.202001673DOI
Stichwörter / KeywordsPROTOTROPIC ISOMERIZATIONS; ALLENES; π -Acids; Amination; Homogeneous catalysis; Oxidations; Selenium
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenZum Teil
URN der UB Regensburgurn:nbn:de:bvb:355-epub-451859
Dokumenten-ID45185

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