Synthesis of Aminoallenes via Selenium-π-Acid-Catalyzed Cross-Coupling of N-Fluorinated Sulfonimides with Simple Alkynes

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.

Automated summary

The facile synthesis of aminoallenes through a selenium-pi-acid-catalyzed cross-coupling of N-fluorinated sulfonimide with simple alkynes has been achieved. This method offers a simple and efficient way to construct the aminoallene motif using ordinary internal alkynes as precursors, tolerating various functional groups and providing the target compounds in up to 86% yield.