Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N ‐Fluorinated Sulfonimides with Simple Alkynes
| Autor: | Alexander Breder, Felix Krätzschmar, Katharina Rode, Poorva Ramadas Narasimhamurthy, Rene Rieger |
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| Rok vydání: | 2021 |
| Předmět: |
Silylation
ddc:540 chemistry.chemical_element Homogeneous catalysis 010402 general chemistry 01 natural sciences Catalysis Selenium chemistry.chemical_compound Oxidations Physical and Theoretical Chemistry Amination π-Acids Amination Homogeneous catalysis Oxidations Selenium 010405 organic chemistry Chemistry Communication Organic Chemistry Combinatorial chemistry Communications 0104 chemical sciences Yield (chemistry) 540 Chemie Functional group Halogen π-Acids |
| Zdroj: | European Journal of Organic Chemistry |
| ISSN: | 1434-193X |
| DOI: | 10.1002/ejoc.202001673 |
| Popis: | 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. A step‐ and redox‐economic route toward aminoallenes from simple alkynes and N‐fluorobenzenesulfonimide (NFSI) was established via selenium‐π‐acid catalysis. This unprecedented method significantly streamlines the assembly of heterosubstituted 1,3‐propadiene motifs and is characterized by a broad functional group tolerance. |
| Databáze: | OpenAIRE |
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