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Synthesis of Aminoallenes via Selenium‐π‐Acid‐Catalyzed Cross‐Coupling of N ‐Fluorinated Sulfonimides with Simple Alkynes
Author(s) -
Rode Katharina,
Ramadas Narasimhamurthy Poorva,
Rieger Rene,
Krätzschmar Felix,
Breder Alexander
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001673
Subject(s) - chemistry , selenium , catalysis , halogen , silylation , yield (engineering) , combinatorial chemistry , organic chemistry , coupling reaction , alkyl , materials science , metallurgy
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.